- Low DNA and high BSA binding affinity of cationic ruthenium(II) organometallic featuring pyridine and 2’-hydroxychalcone ligands
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The chiral-at-metal, piano-stool ruthenium(II) racemic organometallic [Ru(cymene)(chalconato)(pyridine)]PF6 was prepared by a multistep solution synthesis and its molecular and crystal structure was determined by single crystal X-ray diffractio
- Zahirovi?, Adnan,Roca, Sun?ica,Kahrovi?, Emira,Vi?njevac, Aleksandar
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- Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
- Tanemura, Kiyoshi,Rohand, Taoufik
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- Exploring the anti-breast cancer potential of flavonoid analogs
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In the course of our search for new antitumor agents for breast cancer, novel flavone derivatives were synthesized, characterized and examined for their antitumor activities against breast cancer cell lines. In initial screening, analogs 7a [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-phenyl-4H-chromen-4-one] and 7b [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one] were found to be effective against the estrogen receptor negative cell line (MDA-MB 453), which was followed by their evaluation in five dose assays. In addition, mechanistic studies of 7a and 7b were performed by cytometric analysis and electrophoretic studies and it was observed that apoptosis is a mechanism of cell death, confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis. Further in vivo evaluation of the anti-tumor activity of compound 7a and 7b by Ehrlich Ascites Carcinoma (EAC) model and related studies confirms the anti-breast cancer potential of flavonoid analogs.
- Thakor, Vanrajsinh,Poddar, Mayur,Dey, Sumit,Manjula,Madhunapantula, Subbarao V.,Pawara, Rahul,Patel, Harun M.,Noolvi, Malleshappa N.
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- Cytotoxic activity of substituted chalcones in terms of molecular electronic properties
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Global chemical reactivity descriptors and lipophilicity (log P) were evaluated via density functional theory in order to clarify the structure-cytotoxic activity relationships of substituted chalcones. Stepwise multiple regression was employed to establish correlation between descriptors and cytotoxic activity against three cancer cell lines (HL-60, NALM-6 and WM-115) for 11 compounds. Regression analysis revealed that electrophilicity index and chemical potential significantly contributed in explaining of chalcones cytotoxic potential. Moreover, the established structure-activity relationships based on electronic structure properties allow indicating the substructures responsible for their cytotoxic activity. The study has also been supported by crystallographic data of 2-chloro-2′-hydroxychalcone.
- Kupcewicz, Bogumila,Jarzecki, Andrzej A.,Malecka, Magdalena,Krajewska, Urszula,Rozalski, Marek
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- Synthesis of Hierarchically Porous Zeolite Composites with Enhanced Catalytic Activity: Effect of Different Long-Chain Structure Directing Agents
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A two-section temperature strategy was employed to achieve micromesoporous composites with five kinds of long-chain alkyl quaternary ammonium salts as single template. Zeolites with an ordered two-dimensional hexagonal mesopore and crystallized MFI domain were successfully obtained. Gemini quaternary ammonium salt surfactants C18N2 and C22N2 are effective in directing the structure of MCM-41 than CTAB at 100 °C and will transform to lamellar MFI structures at 150 °C gradually. While single quaternary ammonium salts C18N and C22N direct lamellar M41s at 100 °C and transform to mesoporous structure at a higher temperature of 150 °C, it is possible to get a composite of microporous and mesoporous material with a surface area as high as 1046 m2 g-1. Catalytic performance of typical hierarchical zeolites was evaluated by Claisen-Schmidt condensation of bulky reactants. The excellent conversion suggested the synergy effects of improved large molecule diffusion in mesopores and highly separated MFI domains as catalytic centers in the hierarchical zeolites, which can be explained by an apple-tree model.
- Ding, He,Zhang, Yixiao,Xiao, Zixing,Zhang, Jingshuang,Bai, Peng,Li, Najun,Guo, Xianghai
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- Li-Al layered double hydroxides as catalysts for the synthesis of flavanone
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Flavanone was synthesized via a series reaction scheme involving the Claisen-Schmidt condensation between 2′-hydroxyacetophenone and benzaldehyde to form 2′-hydroxychalcone and the subsequent isomerization of 2′-hydroxychalcone to flavanone. Reactions were carried out in the presence of Li-Al layered double hydroxide solid catalyst. The results showed that surface basicity varies with calcination temperature and rehydration. These variations in basicity correlate with the observed catalytic behavior. It is believed that Li+-O2- groups contribute to the surface basicity and are instrumental in the abstraction of a proton from the 2′-hydroxyacetophenone in what is believed to be the first step in the reaction mechanism.
- French, Dustin,Schifano, Paul,Cortés-Concepción, José,Hargrove-Leak, Sirena
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- Primary, secondary, and tertiary silanamine sites formed on nitrided SBA-15 for base catalytic C–C bond formation reactions
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The relationship between catalyst preparation conditions and resulting their catalytic properties on silica substituted nitrogen site, silanamine site, has been discussed for a long time. In this study, the contribution of each silanamine site for several
- Moteki, Takahiko,Koga, Yuuki,Ogura, Masaru
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- Modified Pyridine-Substituted Coumarins: A New Class of Antimicrobial and Antitubercular Agents
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Some new biologically potent coumarin derivatives 7a-f, 8a-f, and 9a-f bearing modified pyridine moieties (indeno[1,2-b]pyridine, 4-azaphenanthrene and benzofuro [3,2-b]pyridine) at the sixth position were designed and synthesized. All the synthesized com
- Giri, Rakesh R.,Lad, Hemali B.,Bhila, Varun G.,Patel, Chirag V.,Brahmbhatt
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- Synthesis of flavanones using nanocrystalline MgO
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The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described.
- Choudary,Ranganath,Yadav, Jagajit,Lakshmi Kantam
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- A new ratiometric ESIPT sensor for detection of palladium species in aqueous solution
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An aqueous ratiometric ESIPT sensor with a 87 nM (15.4 ppb) detection limit was successfully synthesized and applied for detection of all oxidation states of palladium species. The Royal Society of Chemistry 2012.
- Liu, Bin,Wang, Hu,Wang, Taisheng,Bao, Yinyin,Du, Fanfan,Tian, Jiao,Li, Qianbiao,Bai, Ruke
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- Synthesis of nanocrystalline MFI-zeolites with intracrystal mesopores and their application in fine chemical synthesis involving large molecules
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Synthesis of nanocrystalline MFI-zeolite with intracrystal mesopores, to be used to control the size of the zeolite crystals, particle morphology, and mesoporodity, and their application in fine chemical synthesis involving large molecules, was determined. An increase in the amount of PrTES to 5.0 mol% led to spherical macroporous zeolite particles of 300 nm diameter. The mesopores show a pore size distribution in the range of 3-8 nm, while Al and Si MAS MR show that all the samples contain only tetrahedral aluminum sites. It is also proposed that the mesoporous-zeolite crystallization is mediated by the nanoscale segregation of organic-rich and organic-lean domains on the growing zeolite particles. The high catalytic activity of MFI-10PrTES is due to the formation of smaller zeolite crystallites and the presence of intracrystal mesopores.
- Srivastava, Rajendra,Iwasa, Nobuhiro,Fujita, Shin-Ichiro,Arai, Masahiko
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- Synthesis, structure–activity relationship and molecular docking of 3-oxoaurones and 3-thioaurones as acetylcholinesterase and butyrylcholinesterase inhibitors
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The present study describes efficient and facile syntheses of varyingly substituted 3-thioaurones from the corresponding 3-oxoaurones using Lawesson's reagent and phosphorous pentasulfide. In comparison, the latter methodology was proved more convenient, giving higher yields and required short and simple methodology. The structures of synthetic compounds were unambiguously elucidated by IR, MS and NMR spectroscopy. All synthetic compounds were screened for their inhibitory potential against in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Molecular docking studies were also performed in order to examine their binding interactions with AChE and BChE human proteins. Both studies revealed that some of these compounds were found to be good inhibitors against AChE and BChE.
- Mughal, Ehsan Ullah,Sadiq, Amina,Murtaza, Shahzad,Rafique, Hummera,Zafar, Muhammad Naveed,Riaz, Tauqeer,Khan, Bilal Ahmad,Hameed, Abdul,Khan, Khalid Mohammed
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- Hierarchical mesoporous zeolites: Direct self-assembly synthesis in a conventional surfactant solution by kinetic control over the zeolite seed formation
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By kinetic control over the zeolite seed formation, we report the direct fabrication of hierarchical mesoporous zeolites using hexadecyl trimethyl ammonium bromide (CTAB) as the soft template in a conventional solution route. Nanometer-sized, subnanocrystal-type zeolite seeds with a high degree of polymerization are essential to prevent the formation of a separate amorphous mesoporous phase and the phase separation between the mesophase and zeolite crystals in the presence of CTAB and a certain amount of ethanol. The mechanisms for the formation of hierarchically porous zeolites in the solution process, including the effect of mother liquid aging, formation of subnanocrystal zeolite seeds and their self-assembly effect with CTAB, and the role of ethanol are proposed and discussed in detail. The prepared mesoporous ZSM-5 zeolite showed much higher catalytic activity than conventional counterparts for aldol condensations involving large molecules, especially in the synthesis of vesidryl.
- Zhu, Yan,Hua, Zile,Zhou, Jian,Wang, Lijun,Zhao, Jinjin,Gong, Yun,Wu, Wei,Ruan, Meiling,Shi, Jianlin
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- Facile one-pot synthesis of flavanones using tetramethylguanidinum-based ionic liquids as catalysts
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Several tetramethylguanidinum-based ionic liquids (TMGILs) were prepared, characterized and used as catalysts in one-pot synthesis of flavanones. The results indicated that TMGILs composed of phenolate anion was beneficial for one-pot synthesis of flavanones, and [TMG][4-MeO-PhO] induced the good yields of flavanones owing to the electron-donating effect of methoxy substituent on phenolate anion. Furthermore, [TMG][4-MeO-PhO] was found to be used repetitively at least five times without obvious decrease in activity and quantity.
- Zhou, Yan,Huang, Wei,Chen, Xiang-Shu,Song, Zhi-Bin,Tao, Duan-Jian
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- Synthesis and catalytic activity of amino-functionalized SBA-15 materials with controllable channel lengths and amino loadings
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Aminopropyl-functionalized SBA-15 mesoporous materials (NH 2-SBA-15) with different lengths of channeling pores and aminopropyl loadings up to 2.6 mmol g-1 were synthesized by one-pot co-condensation of tetraethyl orthosilicate (TEOS
- Chen, Shih-Yuan,Huang, Ching-Ya,Yokoi, Toshiyuki,Tang, Chih-Yuan,Huang, Shing-Jong,Lee, Jey-Jau,Chan, Jerry C. C.,Tatsumi, Takashi,Cheng, Soofin
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- Sulfonic acid functionalized mesoporous ZSM-5: Synthesis, characterization and catalytic activity in acidic catalysis
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Sulfonic acid functionalized mesoporous ZSM-5 (SO3H-Meso ZSM-5) were prepared by post-grafting of 3-mercaptopropyltriethoxysilane with various loading in the range of 10-50 wt% followed by oxidation of thiol using H2O2 to generate the corresponding sulfonic acid group. Grafting of organic moieties was evidenced by elemental analysis, 29Si & 13C-NMR and X-ray photoelectron spectroscopy. The SO3H-Meso ZSM-5 catalyst with improved acidity and mesoporosity exhibited enhanced catalytic activity in acid-catalyzed liquid-phase reaction of 2′-hydroxyacetophenone and benzaldehyde compared with non-functionalized mesoporous ZSM-5 (Meso ZSM-5) and functionalized microporous ZSM-5 (SO3H-ZSM-5). The higher loading of sulfonic acid functional groups led to higher acidity and consequently resulted in higher yield of products. The catalyst could be reused up to three cycles without significant loss in its catalytic activity.
- Jin, Hailian,Ansari, Mohd Bismillah,Park, Sang-Eon
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- A new pyrazoline-based fluorescent sensor for Al3+ in aqueous solution
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A new pyrazoline-based fluorescent sensor was synthesized and the structure was confirmed by single crystal X-ray diffraction. The sensor responds to Al3+ with high selectivity among a series of cations in aqueous methanol. This sensor forms a
- Hu, Shengli,Song, Jingjing,Wu, Gongying,Cheng, Cuixia,Gao, Qing
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- A simple route to synthesize mesoporous ZSM-5 templated by ammonium-modified chitosan
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Uniform mesoporous zeolite ZSM-5 crystals have been successfully fabricated through a simple hydrothermal synthetic method by utilizing ammonium-modified chitosan and tetrapropylammonium hydroxide (TPAOH) as the meso- and microscale template, respectively. It was revealed that mesopores with diameters of 5-20nm coexisted with microporous network within mesoporous ZSM-5 crystals. Ammonium-modified chitosan was demonstrated to serve as a mesoporogen, self-assembling with the zeolite precursor through strong static interactions. As expected, the prepared mesoporous ZSM-5 exhibited greatly enhanced catalytic activities compared with conventional ZSM-5 and Al-MCM-41 in reactions involving bulky molecules, such as the Claisen-Schmidt condensation of 2-hydroxyacetophenone with benzaldehyde and the esterification reaction of dodecanoic acid and 2-ethylhexanol. Mesoporous zeolite: Ammonium-modified chitosan served as a mesoporogen in the hydrothermal synthesis of mesoporous zeolite Socony Mobil (ZSM)-5, self-assembling with the zeolite precursor through strong static interactions (see figure; TPA=tetrapropylammonium, HTCC=N-(2-hydroxy)propyl-3-trimethylammonium chitosan chloride).
- Jin, Junjiang,Zhang, Xingdi,Li, Yongsheng,Li, Hua,Wu, Wei,Cui, Yunlong,Chen, Qian,Li, Liang,Gu, Jinlou,Zhao, Wenru,Shi, Jianlin
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- Synthesis and in-silico molecular modelling, DFT studies, antiradical and antihyperglycemic activity of novel vanadyl complexes based on chalcone derivatives
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Diabetes mellitus (DM) will be one of the ten most deadly diseases in the near future, according to a WHO survey. It is, therefore, of utmost importance to design and synthesize effective inhibitors to be used in the treatment of DM disease. In this respect, a new series of chalcone derivatives and their vanadyl complexes of composition [VO(LI-III)2]SO4 and [VO(LIV)2] (where LI=1-(2-Hydroxy-phenyl)-3-phenyl-propenone, LII=1-(1-Hydroxy-naphthalen-2-yl)-3-phenyl-propenone, LIII = 1-(2-Amino-phenyl)-3-phenyl-propenone, LIV = 4-Hydroxy-6-methyl-3-(3-phenyl-acryloyl)-pyran-2-one) were designed and synthesized in this work. Physioanalytical, FTIR, 1H NMR, 13C NMR, UV-Visible, EPR, SEM, EDX, and mass spectrometry data were used to establish their formation and validate their structures. After that, biological effects such as antiradical, α-glucosidase, and α-amylase inhibitory activities of synthesized vanadyl-chalcone complexes were assessed. Furthermore, the Density Functional Theory (DFT) studies with 6-31G*/B3LYP level were used to achieve optimal molecular geometries and HOMO-LUMO gap to analyze the chemical and kinetic stability of the complexes. Molecular docking studies were performed as well to investigate the interactions between the synthesized complexes and target enzyme viz. α-amylase and α-glucosidase. The in-vitro biological studies showed major and significant improvements upon the complexation of ligands. Complex 3 (for α-glucosidase) and complex 4 (for α-amylase), in particular, were found to have a remarkable ability to lower blood sugar levels. Otherwise, the potent α-glucosidase and α-amylase inhibitory activity was observed in all of the synthesized complexes. The complexes with the best IC50 values were studied further in terms of enzyme kinetics and displayed mixed inhibition with both enzymes. Furthermore, using the DPPH assay, the antiradical activity of chalcones and their vanadyl complexes was evaluated for their efficacy in releasing oxidative stress. From the obtained results, complex 3 and 4 exhibited remarkable antiradical activity.
- Kaur, Mandeep,Kaushal, Raj
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- Water stable fluorescent organotin(iv) compounds: aggregation induced emission enhancement and recognition of lead ions in an aqueous system
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Herein, synthesis, spectroscopic studies, single-crystal X-ray diffraction, aggregation-induced emission enhancement (AIEE) and sensing application of water-stable organotin(iv) compounds (4a-6aand4b-6b) obtained from 3-hydroxy-4H-chromen-4-one ligands are reported. All the synthesized organotin(iv) compounds were characterized using elemental analysis, FT-IR spectroscopy, multi-nuclei NMR (1H,13C, and119Sn) spectroscopy, UV-VIS, fluorescence spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. The119Sn NMR signal of compounds in the range ofδ?144.92 to ?190.68 ppm indicated the formation of hexacoordinated organotin species. The spectroscopic and single-crystal X-ray diffraction studies confirmed the formation of [L2SnR2] type compounds (where L is the bidentate ligand and R is an alkyl group) with a ‘skew-trapezoidal bipyramidal’ geometry. Furthermore, DFT calculations of compound4bbased on the DGDZVP basis set fully supported the stability of the structure where two short bonds Sn-O(C-O)acquire thecisposition rather than thetransposition. Single-crystal X-ray diffraction analysis of the crystals grown in the presence of water confirmed the stability of4ain water. Moreover, the water stability of a test compound4awas established by119Sn NMR data and spectrofluorimetric data. The spectrofluorimetric scan at different time intervals revealed the stability and constant emission response up to 24 h. The compounds were found to be fluorescent and exhibited aggregation-induced emission enhancement in MeOH/H2O mixtures, which was confirmed by HRTEM analysis. The test compound4ashowed selective spectrofluorimetric recognition of Pb2+ions in an aqueous medium by displaying an enhanced emission signal at 478 nm and enabled detection up to 22.66 μM. A mechanism of interaction is also proposed by spectroscopic experiments, spectrofluorimetric experiments and computational studies.
- Capalash, Neena,Kaur, Kulwinder,Kaur, Varinder,Singh, Raghubir
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p. 148 - 161
(2021/12/31)
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- The influence of the preparation method on the physico-chemical properties and catalytic activities of ce-modified ldh structures used as catalysts in condensation reactions
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Mechanical activation and mechanochemical reactions are the subjects of mechanochem-istry, a special branch of chemistry studied intensively since the 19th century. Herein, we comparably describe two synthesis methods used to obtain the following layered double hydroxide doped with cerium, Mg3 Al0.75 Ce0.25 (OH)8 (CO3)0.5·2H2 O: the mechanochemical route and the co-precipitation method, respectively. The influence of the preparation method on the physico-chemical properties as determined by multiple techniques such as XRD, SEM, EDS, XPS, DRIFT, RAMAN, DR-UV-VIS, ba-sicity, acidity, real/bulk densities, and BET measurements was also analyzed. The obtained samples, abbreviated HTCe-PP (prepared by co-precipitation) and HTCe-MC (prepared by mechanochemical method), and their corresponding mixed oxides, Ce-PP (resulting from HTCe-PP) and Ce-MC (result-ing from HTCe-MC), were used as base catalysts in the self-condensation reaction of cyclohexanone and two Claisen–Schmidt condensations, which involve the reaction between an aromatic aldehyde and a ketone, at different molar ratios to synthesize compounds with significant biologic activity from the flavonoid family, namely chalcone (1,3-diphenyl-2-propen-1-one) and flavone (2-phenyl-4H-1benzoxiran-4-one). The mechanochemical route was shown to have indisputable advantages over the co-precipitation method for both the catalytic activity of the solids and the costs.
- Birjega, Ruxandra,Breze?tean, Ioana,Dumitru, Marius,Marcu, Ioan-Cezar,Matei, Andreea,Osiac, Mariana,Pavel, Octavian Dumitru,Stamate, Alexandra-Elisabeta,Z?voianu, Rodica
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- Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization
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Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.
- Son, Seung Hwan,Cho, Yang Yil,Yoo, Hyung-Seok,Lee, Soo Jin,Kim, Young Min,Jang, Hyu Jeong,Kim, Dong Hwan,Shin, Jeong-Won,Kim, Nam-Jung
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p. 14000 - 14006
(2021/04/22)
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- A novel one-pot synthesis of flavones
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In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
- Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
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p. 11655 - 11662
(2021/03/31)
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- Transfer Hydrogenation of Flavanones and ortho-Hydroxychalcones to 1,3-Diarylpropanols Catalyzed by CNN Pincer Ruthenium Complexes
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The transfer hydrogenation of flavanones and ortho-hydroxychalcones catalyzed by ruthenium pincer complexes RuCl(CNNPh)(disphosphine) has allowed the synthesis of ortho-hydroxy 1,3-diarypropanols in 80–88 % yield, under mild reaction conditions and short reaction times (1 h) in 2-propanol. The amount of the co-catalyst NaOiPr has been found crucial for the selective reduction of flavanones to ortho-hydroxy 1,3-diarypropanols vs. flavan-4-ols. Preliminary results show that with pincer catalysts bearing (S,R)-Josiphos, flavanone is reduced to the corresponding (S)-alcohol in moderate conversion (36 %) and up to 92 % ee.
- Soto, Martín,Gotor-Fernández, Vicente,Rodríguez-Solla, Humberto,Baratta, Walter
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p. 2152 - 2157
(2021/03/03)
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- B regioselective and chemoselective biotransformation of 2′-hydroxychalcone derivatives by marine-derived fungi
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Eight fungal strains (Penicillium raistrickii CBMAI 931, Cladosporium sp. CBMAI 1237, Aspergillus sydowii CBMAI 935, Penicillium oxalicum CBMAI 1996, Penicillium citrinum CBMAI 1186, Mucor racemosus CBMAI 847, Westerdykella sp. CBMAI 1679, and Aspergillus sclerotiorum CBMAI 849) mediated the biotransformation of the 2′-hydroxychalcone 1a. The main products obtained were from hydrogenation, hydroxylation, and cyclization reactions. Penicillium raistrickii CBMAI 931 catalyzed the chemoselective reduction of 1a to produce 2′-hydroxydihydrochalcone 2a (72%) in 7 days of incubation in phosphate buffer (pH 7). Aspergillus sydowii CBMAI 935 promoted the hydroxylation of 1a to yield 2′,4-dihydroxy-dihydrochalcone 5a (c = 42%) in 7 days of incubation in phosphate buffer (pH 8). The reaction using P. citrinum CBMAI 1186 and M. racemosus CBMAI 847 presented main cyclization products in phosphate buffer (pH 8), but the reactions with these fungi did not present enantioselectivity. Marine-derived fungi were effective and versatile biocatalysts for biotransformation of the 2′-hydroxychalcones yielding different products according to the conditions and microorganism used.
- Nitschke, Marcia,Porto, André Luiz Meleiro,de Matos, Iara Lisboa
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- Stereoselective reduction of flavanones by marine-derived fungi
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Biotransformation is an alternative with great potential to modify the structures of natural and synthetic flavonoids. Therefore, the bioreduction of synthetic halogenated flavanones employing marine-derived fungi was described, aiming the synthesis of flavan-4-ols 3a-g with high enantiomeric excesses (ee) of both cis- and trans-diastereoisomers (up to >99% ee). Ten strains were screened for reduction of flavanone 2a in liquid medium and in phosphate buffer solution. The most selective strains Cladosporium sp. CBMAI 1237 and Acremonium sp. CBMAI1676 were employed for reduction of flavanones 2a-g. The fungus Cladosporium sp. CBMAI 1237 presented yields of 72–87% with 0–64% ee cis and 0–30% ee trans with diastereoisomeric ratio (dr) from 52:48 to 64:36 (cis:trans). Whereas Acremonium sp. CBMAI 1676 resulted in 31% yield with 77–99% ee of the cis and 95–99% ee of the trans-diastereoisomers 3a-g with a dr from 54:46 to 96:4 (cis:trans). To our knowledge, this is the first report of the brominated flavon-4-ols 3e and 3f. The use of fungi, with emphasis for these marine-derived strains, is an interesting approach for enantioselective reduction of halogenated flavanones. Therefore, this strategy can be explored to obtain enantioenriched compounds with biological activities.
- Birolli, Willian G.,Nitschke, Marcia,Porto, André Luiz M.,Santos, Darlisson de A.,de Matos, Iara L.
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- Exploring the 2′-hydroxy-chalcone framework for the development of dual antioxidant and soybean lipoxygenase inhibitory agents
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2′-hydroxy-chalcones are naturally occurring compounds with a wide array of bioactiv-ity. In an effort to delineate the structural features that favor antioxidant and lipoxygenase (LOX) inhibitory activity, the design, synthesis, and bioactivity profile of a series of 2′-hydroxy-chalcones bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfac-tory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A, and three methoxy groups on ring B, exhibited the most promising LOX inhibitory activity (IC50 = 45 μM). A combination of in silico techniques were utilized in an effort to explore the crucial binding characteristics of the most active compound 3c and its analogue 3b, to LOX. A common H-bond interaction pattern, orienting the hydroxyl and carbonyl groups of the aromatic ring A towards Asp768 and Asn128, respectively, was observed. Regarding the analogue 3c, the bulky (-OMOM) group does not seem to participate in a direct binding, but it induces an orientation capable to form H-bonds between the methoxy groups of the aromatic ring B with Trp130 and Gly247.
- Detsi, Anastasia,Hadjipavlou-Litina, Dimitra,Karadendrou, Maria-Anna,Kostopoulou, Ioanna,Kritsi, Eftichia,Liargkova, Thalia,Polyzos, Nestor-Ioannis,Pontiki, Eleni,Tzani, Andromachi,Zoumpoulakis, Panagiotis
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- Unsaturated ketone compound as well as preparation method and application thereof
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The present invention relates to a novel GPR52 antagonist. Specifically, the invention relates to an unsaturated ketone compound, a pharmaceutically acceptable salt, a stereoisomer or a prodrug molecule thereof, and a method for preparing a pharmaceutical composition thereof. The invention further relates to the use of the GPR52 antagonist as an orphan G protein coupled receptor GPR52 antagonist,and further relates to the use of the GPR52 antagonist in the preparation of drugs for preventing and treating Huntington's disease.
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Paragraph 0219-0222; 0026-0028
(2020/10/30)
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- Thermally regulated molybdate-based ionic liquids toward molecular oxygen activation for one-pot oxidative cascade catalysis
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One-pot oxidative cascade catalysis plays a central role in the synthesis of key pharmaceutical and industrial molecules. Although ionic liquids are one of the most promising solvents and reaction media, the breakthrough of their catalysis in aerobic oxidation is very challenging due to the difficulty in the direct activation of molecular oxygen. Herein, a family of novel thermally regulated molybdate-based ionic liquids (Mo-ILs) has been designed and developed for the first time toward molecular oxygen activation for highly efficient tandem oxidative catalysis. Three diverse one-pot oxidative cascade processes for the syntheses of various flavones, imines, and benzyl benzoates were achieved with good to excellent yields using the Mo-IL [Bmim]2[MoO4] as a catalyst under air conditions. The results of spectroscopic investigations and quantum-chemical calculations further demonstrated that a thermally regulated proton migration between the cation [Bmim] and anion [MoO4] was the key to forming N-heterocyclic carbene and thereby to effortlessly promoting the generation of O2- active species from molecular oxygen, which results in excellent catalytic performance in these three aerobic tandem oxidations. Our work extends the application area of ILs as the sole catalyst to one-pot aerobic oxidative cascade catalysis, which could have pronounced implications in future work.
- Song, Zhibin,Huang, Wei,Zhou, Yan,Tian, Zi-Qi,Li, Zhang-Min,Tao, Duan-Jian
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p. 103 - 109
(2020/01/21)
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- A Convenient One-Pot Synthesis of Chalcones and Their Derivatives and Their Antimicrobial Activity
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Abstract: A series of chalcones were synthesized by base-catalyzed Clasien-Schmidtcondensation of substituted benzaldehydes and substituted acetophenones at roomtemperature. The addition of hydrazine hydrate and hydroxylamine hydrochlorideacross the double bond of the obtained chalcones gave pyrazole and isoxazolederivatives, respectively. All the synthesized compounds were characterized by1H and 13C NMR andFT-IR spectroscopy and screened for their in vitro antimicrobial activityagainst two bacterial strains, Pseudomonasaeruginosa and Pseudomonasoryzihabitans using Ciprofloxacin as standard drug.1-(2-Methoxyphenyl)-3-phenylprop-2-en-1-one and1-(4-chlorophenyl)-3-phenylprop-2-en-1-one showed significant activity againstboth bacterial strains and hence proved to be potent antimicrobialagents.
- Salotra,Utreja,Sharma
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p. 2207 - 2211
(2021/02/09)
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- Effect of substituents in the A and B rings of chalcones on antiparasite activity
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Chalcones are a group of natural products with many recognized biological activities, including antiparasitic activity. Although a lot of chalcones have been synthetized and assayed against parasites, the number of structural features known to be involved in this biological property is small. Thus, in the present study, 21 chalcones were synthesized to determine the effect of substituents in the A and B rings on the activity against Leishmania braziliensis, Trypanosoma cruzi, and Plasmodium falciparum. The compounds were active against L. braziliensis in a structure-dependent manner. Only one compound was very active against T. cruzi, but none of them had a significant antiplasmodial activity. The electron-donating substituents in ring B and the hydrogen bonds at C-2′ with carbonyl affect the antiparasitic activity.
- González, Luis A.,Upegui, Yulieth A.,Rivas, Luis,Echeverri, Fernando,Escobar, Gustavo,Robledo, Sara M.,Qui?ones, Wiston
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- Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors
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Activating mutations in FLT3 receptor tyrosine kinase are found in a third of acute myeloid leukemia (AML) patients and are associated with disease relapse and a poor prognosis. The majority of these mutations are internal tandem duplications (ITDs) in the juxtamembrane domain of FLT3, which have been validated as a therapeutic target. The clinical success of selective inhibitors targeting oncogenic FLT3, however, has been limited due to the acquisition of drug resistance. Herein the identification of a dual FLT3/microtubule polymerization inhibitor, chalcone 4 (2′-allyloxy-4,4′-dimethoxychalcone), is reported through screening of 15 related chalcones for differential antiproliferative activity in leukemia cell lines dependent on FLT3-ITD (MV-4-11) or BCR-ABL (K562) oncogenes and by subsequent screening for mitotic inducers in the HCT116 cell line. Three natural chalcones (1-3) were found to be differentially more potent toward the MV-4-11 (FLT3-ITD) cell line compared to the K562 (BCR-ABL) cell line. Notably, the new semisynthetic chalcone 4, which is a 2′-O-allyl analogue of the natural chalcone 3, was found to be more potent toward the FLT3-ITD+ cell line and inhibited FLT3 signaling in FLT3-dependent cells. An in vitro kinase assay confirmed that chalcone 4 directly inhibited FLT3. Moreover, chalcone 4 induced mitotic arrest in these cells and inhibited tubulin polymerization in both cellular and biochemical assays. Treatment of MV-4-11 cells with this inhibitor for 24 and 48 h resulted in apoptotic cell death. Finally, chalcone 4 was able to overcome TKD mutation-mediated acquired resistance to FLT3 inhibitors in a MOLM-13 cell line expressing FLT3-ITD with the D835Y mutation. Chalcone 4 is, therefore, a promising lead for the discovery of dual-target FLT3 inhibitors.
- Malik, Haleema Sadia,Bilal, Aishah,Ullah, Rahim,Iqbal, Maheen,Khan, Sardraz,Ahmed, Ishtiaq,Krohn, Karsten,Saleem, Rahman Shah Zaib,Hussain, Hidayat,Faisal, Amir
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p. 3111 - 3121
(2020/11/02)
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- Synthesis and kinetic study for the interconversion process of some 2'-hydroxychalcones to their corresponding flavanones
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In this work, five substituted2'-Hydroxychalconeswere prepared using Claisen - Schmidt condensation and used as a synthone for substituted flavanones via base catalyzed isomerization process. The latter process has been studied kinetically using HPLC technique in (8:2) (CH3CN:CH3OH) medium at different temperatures (298 K - 318 K). The obtained results were inconsonance with a four-step mechanism which considered the existence of phenoxide ion as the key intermediate. The reaction was achieved as a pseudo first order reaction in which the rate of the studied compounds followed the sequence 1>2>3>4>5, and the activation energy had the same sequence for these compounds. The reaction rate was affected by the electronic behavior of the different substituents at ring B since they played an important role in the stability of the intermediate that led to the final product.
- Majed, Zainab Waleed,Said, Said Abdelqader,Shareef, Omar Adil
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p. 4379 - 4386
(2020/12/09)
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- Chloro and bromo-pyrazole curcumin Knoevenagel condensates augmented anticancer activity against human cervical cancer cells: design, synthesis, in silico docking and in vitro cytotoxicity analysis
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With an endeavor to develop novel curcumin analogs as potential anti-cancer agents, we designed and synthesized a series of Knoevenagel condensates by clubbing pyrazole carbaldehydes at the active methylene carbon atom of the curcumin backbone. Molecular docking studies were carried out to target the proposed derivatives on human kinase β (IKKβ), a potential anti-cancer target. The chloro derivative displayed five hydrogen bond interactions with a docking score of ?11.874 kcal/mol higher than curcumin (docking score = ?7.434 kcal/mol). This was supported by the fact that the propellant shaped derivatives fitted aptly into the binding pocket. Molecular simulations studies were also conducted on the lead molecule and the results figured out that the stable complexes were developed as the minimal deviations per residue of protein within the range of 0.11–0.92 ?. The screened compounds were synthesized, characterized and evaluated in vitro for cytotoxicity against cervical cancer cell line, HeLa using standard cell proliferation assay. Chloro derivative and bromo analog demonstrated IC50 (half maximal inhibitory concentration) value of 14.2 and 18.6 μg/ml, respectively, significantly lower than 42.4 μg/ml of curcumin and higher than 0.008 μg/ml of paclitaxel. Induction of apoptosis was evaluated in the terms of cleavage of caspase-3 enzyme and they also exhibited 69.6 and 65.4% of apoptosis significantly higher than 19.9% induced by curcumin. In conclusion, chloro and bromo derivatives must be evaluated under a set of stringent in vitro and in vivo parameters for translating in to a clinically viable product. Communicated by Ramaswamy H. Sarma.
- Chaudhary, Monika,Kumar, Neeraj,Baldi, Ashish,Chandra, Ramesh,Arockia Babu,Madan, Jitender
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p. 200 - 218
(2019/03/08)
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- Synthesis and kinetic investigations for the isomerization process of 2–hydroxy chalcone derivatives
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The wide biological activities of flavanones are mainly depends on their physical and chemical properties, thus a number of substituted 2-Hydroxy chalcones have been synthesized, and their isomerization to their corresponding flavanones was studied. In order to determine the rate constant, kinetic experiments were performed using HPLC technique in (9:1) (CH3CN:H2O) medium at different temperature (298-318) K. The obtained results were interpreted by four steps mechanism, which considered the existence of phenoxide ion as the key intermediate. This study performed with a pseudo first order (reaction in which the rate for the studied compounds follow the sequence 5 > 2 > 1 > 4 > 3, the activation energy have the same sequence for these compounds .The effect of substituents on the rate showed that electronic and steric factors play reasonable role on the stability of the product .
- Shareef, Omar A.,Said, Said A.,Abdulrazaq, Ali Y.
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p. 1046 - 1054
(2020/01/09)
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- Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents
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A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.
- Zhong, Hui,Zhou, Jia,An, Xiao-Hong,Hua, Ying-Rong,Lai, Yi-Fan,Zhang, Rui,Ahmad, Owais,Zhang, Ye,Shang, Jing
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p. 523 - 533
(2019/04/01)
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- Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi
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Chagas disease is caused by infection with the parasite protozoan Trypanosoma cruzi and affects about 8 million people in 21 countries in Latin America. The main form of treatment of this disease is still based on the use of two drugs, benznidazole and nifurtimox, which both present low cure rates in the chronic phase and often have serious side-effects. Herein, we describe the synthesis of tricyclic coumarins that were obtained via NHC organocatalysis and evaluation of their trypanocidal activity. Molecular docking studies against trypanosomal enzyme triosephosphate isomerase (TIM) were carried out, as well as a theoretical study of the physicochemical parameters. The tricyclic coumarins were tested in vitro against the intracellular forms of Trypanosoma cruzi. Among the 18 compounds tested, 10 were more active than the reference drug benznidazole. The trypanocidal activity of the lead compound was rationalized by molecular docking study which suggested the strong interaction with the enzyme TIM by T.?cruzi and therefore indicating a possible mode of action. Furthermore, the selectivity index of eight tricyclic coumarins with high anti-T.?cruzi activity was above 50 and thus showing that these lead compounds are viable candidates for further in vivo assays.
- Coelho, Gleicekelly Silva,Andrade, Josimara Souza,Xavier, Viviane Flores,Sales Junior, Policarpo Ademar,Rodrigues de Araujo, Barbara Caroline,Fonseca, Kátia da Silva,Caetano, Melissa Soares,Murta, Silvane Maria Fonseca,Vieira, Paula Melo,Carneiro, Claudia Martins,Taylor, Jason Guy
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p. 337 - 350
(2018/12/05)
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- Synthesis of 3-HCF2S-Chromones through Tandem Oxa-Michael Addition and Oxidative Difluoromethylthiolation
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A simple protocol for the synthesis of difluoromethylthiolated chromen-4-ones using elemental sulfur and ClCF2CO2Na as the difluoromethylthiolating agent is described. Three-component reactions of 2′-hydroxychalcones, ClCF2CO2Na, and sulfur under basic conditions using TEMPO as the oxidant afforded HCF2S-containing 4H-chromen-4-one and 9H-thieno[3,2-b]chromen-9-one derivatives in good yield. The protocol is practical and efficient, and the starting materials are cheap and readily available.
- Zhang, Pingshun,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 9326 - 9329
(2019/12/24)
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- The detection of the precursors of the photorearranged products of 3-hydroxyflavones in selected solvents from UV-visible spectra: In situ
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Mechanistic studies relating to the photochemistry of 3-hydroxy-2-phenyl-4H-chromen-4-one (3HF) and 6-chloro-3-hydroxy-2-phenyl-4H-chromen-4-one (Cl-3HF) have been reinvestigated in selected solvents. The UV-visible spectra of the photoproduct(s) of 3HF and Cl-3HF have been computed in situ via subtracting the spectra of unreacted substrates, with acetonitrile (ACN) and methanol (MeOH) as solvents. These spectra turn out to be different from the spectra of the corresponding isolated photoproducts: 3-hydroxy-3-phenyl-indan-1,2-dione and 6-chloro-3-hydroxy-3-phenyl-indan-1,2-dione (referred to as dione). Analyses of the photoproduct(s) via GC-MS show the formation of a single detectable product, i.e., the corresponding dione. On the basis of some experimental observations, it is proposed that the primary photoproduct in situ is 2,3-epoxy-2-hydroxy-1-indanone (referred to as epoxide) instead of dione as reported in previous years. Earlier, epoxide has been proposed to be the intermediate in the mechanism for the formation of dione. This is the first report where the formation of epoxide has been directly detected in the selected solvents. On the other hand, both dione and epoxide (2?:?1) are shown to be formed with MeOH as solvent. The second important finding is that epoxide and dione interconvert in the dark, depending upon the environment. With ACN as solvent, pure dione in the dark is kinetically and partially converted to epoxide. With MeOH as solvent, epoxide is instantly and partially converted to dione until both are in equilibrium. However, a solution of dione in MeOH remains stable in the dark. The photoformation of epoxide is quantitative with ACN as solvent and it is sufficiently stable. It has been further observed that epoxide solutions of 3HF and Cl-3HF in ACN are quantitatively converted into 3-phenylisobenzofuran-1(3H)-one and 6-chloro-3-phenylisobenzofuran-1(3H)-one, i.e., the corresponding phthalides, through the loss of CO when kept in the dark for some days. A mechanism has been proposed where epoxide has been shown to give dione and/or phthalide via selective C-O or C-C bond cleavage in the oxiranyl ring, respectively. The selection of this cleavage depends mainly on the solvent system and the substituents in the parent flavones.
- Tomar, Jyoti,Kaur, Kulvir,Bansal, Manisha
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p. 2912 - 2920
(2019/12/24)
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- Design, synthesis and biological evaluation of novel dihydropyrimidine-2-thione derivatives as potent antimicrobial agents: Experimental and molecular docking approach
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Introduction: Dihydropyrimidine scaffold represent an important class of pharmacologically active nitrogen containing heterocyclic compounds. A wide range of molecules with dihydropyrimidine moieties have important role in medicinal chemistry on account of their potential biological activities. Methodology: A series of 3,4-dihydropyrimidine-2(1H)-thione derivatives have been designed and synthesized in a concise way through condensation of variously substituted chalcones with thiourea in alkaline alcoholic solutions. In order to investigate their biological significance, these compounds were tested for their in vitro antimicrobial potential against various bacterial and fungal strains. Moreover, the experimental results were supported by molecular docking studies. Results and Discussion: The newly synthesized compounds were characterized by the usual spectroscopic techniques In case of antibacterial activity, the compounds 5 (40.3±0.44 mm), 12 and 13 (almost 35 mm) exhibited highest zone of inhibitions against Methicillin-resistant Staphylococcus auerus (MRSA) bacterial strain as compared to the standard drug Cefixime. These compounds displayed moderate to good activities against all attempted fungal strains. In docking analysis, it has been observed that compounds 8 (-6.4017 Kcal/mol) and 10 (-6.1319 Kcal/mol) revealed significant binding affinity against penicillin binding protein (PDB ID: 1VQQ), while compounds 1 (-143.23 Kcal/mol) and 2 (-146.99 Kcal/mol) showed best activity for shikimate dehydrogenase (PDB ID: 3DON). Conclusion: In conclusion, we have designed, synthesized and characterized an interesting series of biologically active dihydropyrimidine derivatives. Remarkably, most of the synthesized compounds were found more active against all tested bacterial strains in comparison to the standard drug Cefixime as manifested by experimental as well as theoretical results.
- Mughal, Ehsan Ullah,Sadiq, Amina,Hamayun, Muhammad,Zafar, Muhammad Naveed,Fatima, Nighat,Yameen, Muhammad Arfat,Muhammad, Syed Aun,Mumtaz, Amara,Ahmed, Ishtiaq,Fatima, Tehseen
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p. 1189 - 1201
(2018/11/01)
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- Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids
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Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.
- Lu, Yanhui,Nakatsuji, Hidefumi,Okumura, Yukimasa,Yao, Lu,Ishihara, Kazuaki
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supporting information
p. 6039 - 6043
(2018/05/14)
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- Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction
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The first decarbonylative insertion of an alkyne through C?H/C?C activation of six-membered compounds is reported. The Ru-catalyzed reaction of 3-hydroxy-2-phenyl-chromones with alkynes works most efficiently in the presence of the ligand PPh3 to provide spiro-indenebenzofuranones. Unlike previously reported metal-catalyzed decarbonylative annulation reactions, in the present decarbonylative annulation reaction, the annulation occurs before extrusion of carbon monoxide.
- Kaishap, Partha P.,Duarah, Gauri,Sarma, Bipul,Chetia, Dipak,Gogoi, Sanjib
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supporting information
p. 456 - 460
(2018/02/21)
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- Thermal study of chalcones: Thermal decomposition of chalcone and its hydroxylated derivatives
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Chalcones α-β-unsaturated ketones are found in large plant species. Synthesis of chalcones and its three analogues hydroxy group at 2′, 3′ and 4′ positions (2–4) was carried out. The studies of thermal behavior were made by thermogravimetry (TG) and differential scanning calorimetry, both under oxygen and nitrogen purge gases. In addition, the kinetic evaluation was carried out under heating rates of 5, 10 and 20?°C?min?1 with sample mass of 2?mg in open crucibles. The kinetic results obtained by TG analysis showed that the thermal behavior under oxygen shows that the functional hydroxy group substitution affects the thermal behavior of each molecule, with a gradual increase in the thermal decomposition. The activation energy (Ea/kJ?mol?1) showed under a nitrogen purge gas that the hydroxy group at 3′ position (3′-hy-chalcone compound) has a different kinetic behavior, while the chalcone under oxygen showed a low activation energy when compared with the other hydroxy groups.
- Kobelnik, Marcelo,Ferreira, Leonardo Miziara Barboza,Regasini, Luis Octavio,Dutra, Luiz Antonio,da Silva Bolzani, Vanderlan,Ribeiro, Clóvis Augusto
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p. 425 - 431
(2018/02/06)
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- Design, Synthesis, and Biological Evaluation of Pyrazoline-Based Hydroxamic Acid Derivatives as Aminopeptidase N (APN) Inhibitors
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Aminopeptidase N (APN) has been recognized as a target for anticancer treatment due to its overexpression on diverse malignant tumor cells and association with cancer invasion, metastasis and angiogenesis. Herein we describe the synthesis, biological evaluation, and structure–activity relationship study of two new series of pyrazoline analogues as APN inhibitors. Among these compounds, 5-(2-(2-(hydroxyamino)-2-oxoethoxy)phenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (compound 13 e) showed the best APN inhibition with an IC50 value of 0.16±0.02 μm, which is more than one order of magnitude lower than that of bestatin (IC50=9.4±0.5 μm). Moreover, compound 13 e was found to inhibit the proliferation of diverse carcinoma cells and to show potent anti-angiogenesis activity. At the same concentration, compound 13 e presents significantly higher anti-angiogenesis activity than bestatin in human umbilical vein endothelial cells (HUVECs) capillary tube formation assays. The putative binding mode of 13 e in the active site of APN is also discussed.
- Cao, Jiangying,Zang, Jie,Ma, Chunhua,Li, Xiaoguang,Hou, Jinning,Li, Jin,Huang, Yongxue,Xu, Wenfang,Wang, Binghe,Zhang, Yingjie
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supporting information
p. 431 - 436
(2018/02/21)
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- Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
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Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and showed various efficiency. Compounds D1–D30 showed no toxic effects on RAW 264.7 cells at the concentration 20 μM; among them, compounds D9, D13, and D19 exhibited best anti-inflammatory activity through decreasing IL-1β, IL-6, and TNF-α. Furthermore, their structure–activity relationships were discussed preliminarily.
- Hu, Chunling,Zhou, Zongbao,Xiang, Yuanhang,Song, Xiaoying,Wang, Hong,Tao, Kaiqi,Ye, Xiaochuan
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p. 194 - 205
(2018/04/19)
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- Preparation method for cadmium, aluminium and lead ion chelating agent
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The invention discloses a preparation method for a metal ion chelating agent, belongs to the field of analytical chemistry and environment, and particularly relates to the preparation method for the metal ion chelating agent and application thereof in tre
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Paragraph 0005
(2018/04/03)
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- Synthesis, structure-activity relationship and molecular docking studies of 3-O-flavonol glycosides as cholinesterase inhibitors
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The prime objective of this research work is to prepare readily soluble synthetic analogues of naturally occurring 3-O-flavonol glycosides and then investigate the influence of various substituents on biological properties of synthetic compounds. In this context, a series of varyingly substituted 3-O-flavonol glycosides have been designed, synthesized and characterized efficiently. The structures of synthetic molecules were unambiguously corroborated by IR, 1H, 13C NMR and ESI-MS spectroscopic techniques. The structure of compound 22 was also analyzed by X-ray diffraction analysis. All the synthetic compounds (21–30) were evaluated for in vitro inhibitory potential against cholinesterase enzymes. The results displayed that most of the derivatives were potent inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with varying degree of IC50 values. The experimental results were further encouraged by molecular docking studies in order to explore their binding behavior with the active pocket of AChE and BChE enzymes. The experimental and theoretical results are in parallel with one another.
- Mughal, Ehsan Ullah,Javid, Asif,Sadiq, Amina,Murtaza, Shahzad,Zafar, Muhammad Naveed,Khan, Bilal Ahmad,Sumra, Sajjad Hussain,Tahir, Muhammad Nawaz,Kanwal,Khan, Khalid Mohammed
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p. 3696 - 3706
(2018/06/19)
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- Iodine-mediated direct synthesis of 3-iodoflavones
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Molecular iodine has been used for the regioselective, one pot, direct synthesis of 3-iodoflavones from 2′-allyloxy chalcones, 2′-hydroxy chalcones and flavones. Allyl deprotection, cyclization dehydrogenation and α-iodination of 2′-allyloxychalcones has been achieved in a single step to offer 3-iodoflavones.
- Patil, Avinash M.,Kamble, Dayanand A.,Lokhande, Pradeep D.
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p. 1299 - 1307
(2018/04/05)
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- Guanidino-graphene catalysed synthesis of flavones via Aldol-Michael-oxidation
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Guanidino-graphene has been synthesized by the reaction of bromoamine with reduced graphene oxide and characterized by FT-IR, Raman, TGA, powder XRD, TEM, SEM, and zeta potential. It is a cheap, heterogeneous and environmentally benign solid base catalyst used for cascade Aldol-Michael-oxidation in the synthesis of chalcone, flavonoids.
- Mishra, Sweta,Arora, Smriti,Nagpal, Ritika,Chauhan, Shive Murat Singh
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p. 2525 - 2530
(2017/03/09)
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- Synthesis, molecular docking studies and biological evaluation of 3-iminoaurones as acetylcholinesterase and butyrylcholinesterase inhibitors
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Background: A new series of aurone-hydrazones have been designed and synthesized in order to explore new bioactive compounds, which could have potential to be used as active drugs against Alzheimer’s disease. Methods: The newly synthesized compounds were characterized by various spectroscopic techniques (IR, mass spectrometry and NMR spectroscopy) and evaluated in vitro for their inhibitory potential against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. All target compounds exhibited varied degree of IC50 values compared to standard Donepezil. Among the series, the compound 6c was found as a potent dual inhibitor of AChE and BChE having IC50 values 0.92±0.01 and 2.25±0.01 μM respectively. Results and Conclusion: The experimental results were further supported by molecular docking analysis. Both studies showed that some of these compounds are interesting inhibitors against AChE and BChE enzymes.
- Mughal, Ehsan Ullah,Sadiq, Amina,Khan, Bilal Ahmad,Zafar, Muhammad Naveed,Ahmed, Ishtiaq,Zubair, Muhammad
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p. 1035 - 1041
(2017/09/12)
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- Graphene-supported ZnO nanoparticles: An efficient heterogeneous catalyst for the Claisen-Schmidt condensation reaction without additional base
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ZnO nanoparticles supported on reduced graphene oxide (ZnO/RGO) were prepared by the hydrothermal method and characterized by TEM, XPS, XRD, and Raman spectroscopy. As a green catalyst, ZnO/RGO was applied to the Claisen-Schmidt condensation reaction of aryl aldehydes and aryl ketones under microwave irradiation. Therein, chalcone products could be efficiently synthesized and easily separated from the heterogeneous catalysis system. The catalyst could be recycled four times without significant loss of catalytic activity.
- Li, Zhuofei,Zhao, Hongyan,Han, Huatao,Liu, Yang,Song, Jinyi,Guo, Weihao,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 3984 - 3988
(2017/09/26)
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- Synthesis, crystal structure and antitumour activity evaluation of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives
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A series of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives were synthesised through Knoevenagel condensation of substituted flavanones with thiazolidine-2,4-dione in ethanol in the presence of piperidine. The mechanism of the reaction was proposed. All synthesised compounds were characterised by IR, 1H NMR, 13C NMR, HRMS, and elemental analysis. The structure of 2-(3-chlorophenyl)-1H-thieno[2,3-c]chromen-4(2H)-one was confirmed by a single crystal X-ray diffraction analysis. A preliminary antitumour screening showed that 2-(2-fluorophenyl)-1H-thieno [2,3-c]chromen-4(2H)-one had moderate to good activity against A549, BGC-823, HCT116 and MDA-MB-453 cancer cell lines, and 2-(3,4-dimethoxyphenyl)-1H-thieno[2,3-c]chromen-4(2H)-one displayed similar activity against these four kinds of cancer cells compared with the reference drug.
- Yu, Huchang,Li, Yan,Feng, Zhiyuan,Jiang, Hongwu,Zhao, Yinglan,Luo, Youfu,Huang, Wencai,Li, Zicheng
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- Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives
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A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1–20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1–5, 7–17, 19) were found to be selective towards hMAO-B, while two w
- Badavath, Vishnu Nayak,Nath, Chandrani,Ganta, Narayana Murthy,Ucar, Gulberk,Sinha, Barij Nayan,Jayaprakash, Venkatesan
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p. 1528 - 1532
(2017/07/17)
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- Efficient Access to Chromeno[4,3- b ]quinolines Related to Dependensin
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We report a robust synthesis of novel chromeno[4,3- b ]quinoline derivatives structurally similar to the natural product dependensin. The target compounds are accessed through the acid-catalysed condensation of 2-aminoacetophenones or 2-aminochalcones with substituted flavanones, which are in turn obtained from 2-hydroxyacetophenones and benzaldehydes.
- Dobrowolski, Jeremy C.,Fraser, Benjamin H.,Bhadbhade, Mohan,Black, David Stc.,Kumar, Naresh
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p. 1979 - 1983
(2017/09/13)
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- Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloaddition and Its Application in Natural Product Synthesis
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An efficient method for the asymmetric Diels-Alder cycloaddition of 2'-hydroxychalcones with acyclic or cyclic dienes has been successfully developed. The Diels-Alder cycloaddition is mediated by a chiral boron complex with VANOL, affording the corresponding products in high yields and with excellent diastereo- and enantioselectivities. This reaction enabled the enantioselective construction of cyclohexene skeletons crucial for the total synthesis of a number of Diels-Alder-type natural products (-)-nicolaioidesin C, (-)-panduratine A, (-)-kuwanon I, (+)-kuwanon J, and (-)-brosimones A and B.
- Li, Xia,Han, Jianguang,Jones, Alexander X.,Lei, Xiaoguang
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supporting information
p. 458 - 468
(2016/01/25)
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- A new series of 2-phenol-4-aryl-6-chlorophenyl pyridine derivatives as dual topoisomerase I/II inhibitors: Synthesis, biological evaluation and 3D-QSAR study
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As a continuous effort to develop novel antitumor agents, a new series of forty-five 2-phenol-4-aryl-6-chlorophenyl pyridine compounds were synthesized and evaluated for cytotoxicity against four different human cancer cell lines (DU145, HCT15, T47D, and HeLa), and topoisomerase I and II inhibitory activity. Several compounds (10-15, 20, 22, 24, 28, 42, and 49) displayed strong to moderate dual topoisomerase I and II inhibitory activity at 100 μM. It was observed that hydroxyl and chlorine moiety at meta or para position of phenyl ring is favorable for dual topoisomerase inhibitory activity and cytotoxicity. Most of the compounds displayed stronger cytotoxicities than those of all positive controls against the HCT15 and T47D cell lines. For investigation of the structure-activity relationships, a 3D-QSAR analysis using the method of comparative molecular field analysis (CoMFA) was performed. The generated 3D contour maps can be used for further rational design of novel terpyridine derivatives as highly selective and potent cytotoxic agents.
- Karki, Radha,Jun, Kyu-Yeon,Kadayat, Tara Man,Shin, Somin,Thapa Magar, Til Bahadur,Bist, Ganesh,Shrestha, Aarajana,Na, Younghwa,Kwon, Youngjoo,Lee, Eung-Seok
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p. 228 - 245
(2016/03/08)
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- QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase
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Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.
- Yaeghoobi, Marzieh,Frimayanti, Neni,Chee, Chin Fei,Ikram, Kusaira K.,Najjar, Belal O.,Zain, Sharifuddin M.,Abdullah, Zanariah,Wahab, Habibah A.,Rahman, Noorsaadah Abd.
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p. 2133 - 2142
(2016/10/25)
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- Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus
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A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.
- Badavath, Vishnu N.,Jadav, Surender S.,Pastorino, Boris,De Lamballerie, Xavier,Sinha, Barij N.,Jayaprakash, Venkatesan
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p. 1019 - 1024
(2016/11/25)
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- Synthesis, biological evaluation and molecular modelling of 2′-hydroxychalcones as acetylcholinesterase inhibitors
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A series of 2′-hydroxy- and 2′-hydroxy-4′,6′-dimethoxychalcones was synthesised and evaluated as inhibitors of human acetylcholinesterase (AChE). The majority of the compounds were found to show some activity, with the most active compounds having IC
- Sukumaran, Sri Devi,Chee, Chin Fei,Viswanathan, Geetha,Buckle, Michael J. C.,Othman, Rozana,Rahman, Noorsaadah Abd.,Chung, Lip Yong
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- Gold Nanoparticles Supported on a Layered Double Hydroxide as Efficient Catalysts for the One-Pot Synthesis of Flavones
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Flavones are a class of natural products with diverse biological activities and have frequently been synthesized by step-by-step procedures using stoichiometric amounts of reagents. Herein, a catalytic one-pot procedure for the synthesis of flavone and its derivatives is developed. In the presence of gold nanoparticles supported on a Mg-Al layered double hydroxide (Au/LDH), various kinds of flavones can be synthesized starting from 2′-hydroxyacetophenones and benzaldehydes (or benzyl alcohols). The present one-pot procedure consists of a sequence of several reactions, and Au/LDH can catalyze all these different types of reactions. The catalysis is shown to be truly heterogeneous, and Au/LDH can be readily recovered and reused. Go for gold: In the presence of gold nanoparticles supported on a Mg-Al layered double hydroxide (Au/LDH), various flavones were obtained from the corresponding 2′-hydroxyacetophenones and benzaldehydes (or benzyl alcohols). All three (four) steps of this one-pot process are catalyzed by Au/LDH in a truly heterogeneous fashion.
- Yatabe, Takafumi,Jin, Xiongjie,Yamaguchi, Kazuya,Mizuno, Noritaka
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supporting information
p. 13302 - 13306
(2015/11/09)
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- Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives
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Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes and substituted salicylaldehyes. The resulting 2,3-disubstituted chroman-4-ones are readily fluorinated to form trans-3-fluoro-2,3-disubstituted chroman-4-ones in high yields with excellent diastereoselectivity. (Chemical Equation Presented).
- Du, Xiang-Wei,Stanley, Levi M.
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p. 3276 - 3279
(2015/07/15)
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- The synthesis and structures of arene-substituted azadipyrromethenes
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We present the synthesis of several azadipyrromethenes with four peripheral arene units which can be readily generated via the well-established chalcone synthetic method. The stability and yields of these azadipyrromethenes is highly dependent on the nature of the arene substituent, with the bis-pyridine systems exhibiting the highest degree of instability. The structures of several of the compounds and their BF2 adducts are presented; intramolecular hydrogen bonding is observed in the free base ADPMs. We also present a study into the absorption and emission properties of the ADPMs and their BF2 adducts and observe that they are also highly dependent on the identity of the substituents.
- Chanawanno, Kullapa,Hasheminasab, Abed,Engle, James T.,Ziegler, Christopher J.
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p. 276 - 281
(2015/10/19)
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