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Cas Database

1214-47-7

1214-47-7

Identification

Synonyms:Chalcone,2'-hydroxy- (6CI,7CI,8CI);1-(2-Hydroxyphenyl)-3-phenyl-2-propen-1-one;2-(3-Phenyl-2-propenoyl)phenol;2'-Hydroxychalcone;3-Phenyl-1-(2-hydroxyphenyl)-2-propen-1-one;NSC 18939;RVC 556;o-Cinnamoylphenol;o-Hydroxychalcone;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:2''-Hydroxychalcone
  • Packaging:250mg
  • Price:$ 45
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2'-Hydroxychalcone >98.0%(HPLC)
  • Packaging:25g
  • Price:$ 68
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-(2-Hydroxyphenyl)-3-phenyl-2-propenone for synthesis
  • Packaging:25 g
  • Price:$ 68.5
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2'-HYDROXYCHALCONE Aldrich
  • Packaging:250mg
  • Price:$ 144
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-(2-Hydroxyphenyl)-3-phenyl-2-propenone for synthesis. CAS 1214-47-7, molar mass 224.26 g/mol., for synthesis
  • Packaging:8147760025
  • Price:$ 66.2
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-(2-Hydroxyphenyl)-3-phenyl-2-propenone for synthesis. CAS 1214-47-7, molar mass 224.26 g/mol., for synthesis
  • Packaging:8147760100
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-(2-Hydroxyphenyl)-3-phenyl-2-propenone for synthesis
  • Packaging:100 g
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  • Manufacture/Brand:Crysdot
  • Product Description:1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one 97%
  • Packaging:500g
  • Price:$ 240
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  • Manufacture/Brand:Crysdot
  • Product Description:1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one 97%
  • Packaging:100g
  • Price:$ 75
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  • Manufacture/Brand:Crysdot
  • Product Description:1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one 97%
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Relevant articles and documentsAll total 137 Articles be found

Low DNA and high BSA binding affinity of cationic ruthenium(II) organometallic featuring pyridine and 2’-hydroxychalcone ligands

Zahirovi?, Adnan,Roca, Sun?ica,Kahrovi?, Emira,Vi?njevac, Aleksandar

, (2021)

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

Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water

Tanemura, Kiyoshi,Rohand, Taoufik

, (2021)

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.

Exploring 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.

, p. 79166 - 79179 (2016)

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.

Cytotoxic activity of substituted chalcones in terms of molecular electronic properties

Kupcewicz, Bogumila,Jarzecki, Andrzej A.,Malecka, Magdalena,Krajewska, Urszula,Rozalski, Marek

, p. 4260 - 4265 (2014)

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.

Synthesis of Hierarchically Porous Zeolite Composites with Enhanced Catalytic Activity: Effect of Different Long-Chain Structure Directing Agents

Ding, He,Zhang, Yixiao,Xiao, Zixing,Zhang, Jingshuang,Bai, Peng,Li, Najun,Guo, Xianghai

, p. 1730 - 1737 (2018)

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.

Li-Al layered double hydroxides as catalysts for the synthesis of flavanone

French, Dustin,Schifano, Paul,Cortés-Concepción, José,Hargrove-Leak, Sirena

, p. 92 - 94 (2010)

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.

Primary, secondary, and tertiary silanamine sites formed on nitrided SBA-15 for base catalytic C–C bond formation reactions

Moteki, Takahiko,Koga, Yuuki,Ogura, Masaru

, p. 131 - 139 (2019)

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

Modified Pyridine-Substituted Coumarins: A New Class of Antimicrobial and Antitubercular Agents

Giri, Rakesh R.,Lad, Hemali B.,Bhila, Varun G.,Patel, Chirag V.,Brahmbhatt

, p. 363 - 375 (2015)

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

Synthesis of flavanones using nanocrystalline MgO

Choudary,Ranganath,Yadav, Jagajit,Lakshmi Kantam

, p. 1369 - 1371 (2005)

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.

A new ratiometric ESIPT sensor for detection of palladium species in aqueous solution

Liu, Bin,Wang, Hu,Wang, Taisheng,Bao, Yinyin,Du, Fanfan,Tian, Jiao,Li, Qianbiao,Bai, Ruke

, p. 2867 - 2869 (2012)

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.

Synthesis of nanocrystalline MFI-zeolites with intracrystal mesopores and their application in fine chemical synthesis involving large molecules

Srivastava, Rajendra,Iwasa, Nobuhiro,Fujita, Shin-Ichiro,Arai, Masahiko

, p. 9507 - 9511 (2008)

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.

Synthesis, structure–activity relationship and molecular docking of 3-oxoaurones and 3-thioaurones as acetylcholinesterase and butyrylcholinesterase inhibitors

Mughal, Ehsan Ullah,Sadiq, Amina,Murtaza, Shahzad,Rafique, Hummera,Zafar, Muhammad Naveed,Riaz, Tauqeer,Khan, Bilal Ahmad,Hameed, Abdul,Khan, Khalid Mohammed

, p. 100 - 106 (2017)

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.

Hierarchical mesoporous zeolites: Direct self-assembly synthesis in a conventional surfactant solution by kinetic control over the zeolite seed formation

Zhu, Yan,Hua, Zile,Zhou, Jian,Wang, Lijun,Zhao, Jinjin,Gong, Yun,Wu, Wei,Ruan, Meiling,Shi, Jianlin

, p. 14618 - 14627 (2011)

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.

Facile one-pot synthesis of flavanones using tetramethylguanidinum-based ionic liquids as catalysts

Zhou, Yan,Huang, Wei,Chen, Xiang-Shu,Song, Zhi-Bin,Tao, Duan-Jian

, p. 1830 - 1836 (2015)

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.

Synthesis and catalytic activity of amino-functionalized SBA-15 materials with controllable channel lengths and amino loadings

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

, p. 2233 - 2243 (2012)

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

Sulfonic acid functionalized mesoporous ZSM-5: Synthesis, characterization and catalytic activity in acidic catalysis

Jin, Hailian,Ansari, Mohd Bismillah,Park, Sang-Eon

, p. 116 - 121 (2015)

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.

A new pyrazoline-based fluorescent sensor for Al3+ in aqueous solution

Hu, Shengli,Song, Jingjing,Wu, Gongying,Cheng, Cuixia,Gao, Qing

, p. 1188 - 1194 (2015)

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

Naidu

, p. 124 (1972)

A simple route to synthesize mesoporous ZSM-5 templated by ammonium-modified chitosan

Jin, Junjiang,Zhang, Xingdi,Li, Yongsheng,Li, Hua,Wu, Wei,Cui, Yunlong,Chen, Qian,Li, Liang,Gu, Jinlou,Zhao, Wenru,Shi, Jianlin

, p. 16549 - 16555 (2012)

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).

Synthesis and in-silico molecular modelling, DFT studies, antiradical and antihyperglycemic activity of novel vanadyl complexes based on chalcone derivatives

Kaur, Mandeep,Kaushal, Raj

, (2022/01/13)

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.

Water stable fluorescent organotin(iv) compounds: aggregation induced emission enhancement and recognition of lead ions in an aqueous system

Capalash, Neena,Kaur, Kulwinder,Kaur, Varinder,Singh, Raghubir

, p. 148 - 161 (2021/12/31)

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.

B regioselective and chemoselective biotransformation of 2′-hydroxychalcone derivatives by marine-derived fungi

Nitschke, Marcia,Porto, André Luiz Meleiro,de Matos, Iara Lisboa

, (2021/08/06)

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.

Stereoselective reduction of flavanones by marine-derived fungi

Birolli, Willian G.,Nitschke, Marcia,Porto, André Luiz M.,Santos, Darlisson de A.,de Matos, Iara L.

, (2021/08/13)

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.

Exploring the 2′-hydroxy-chalcone framework for the development of dual antioxidant and soybean lipoxygenase inhibitory agents

Detsi, Anastasia,Hadjipavlou-Litina, Dimitra,Karadendrou, Maria-Anna,Kostopoulou, Ioanna,Kritsi, Eftichia,Liargkova, Thalia,Polyzos, Nestor-Ioannis,Pontiki, Eleni,Tzani, Andromachi,Zoumpoulakis, Panagiotis

, (2021/05/29)

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.

Process route upstream and downstream products

Process route

phenyl cinnamate
2757-04-2,25695-77-6

phenyl cinnamate

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
With sodium dodecyl-sulfate; for 7h; Irradiation;
15%
70%
salicylaldehyde
90-02-8

salicylaldehyde

phenylacetylene
536-74-3

phenylacetylene

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
With piperidine; iron(III) chloride; In toluene; for 8h; Reflux;
80%
4%
Flavanone
487-26-3

Flavanone

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
With gold nanoparticles supported on a Mg-Al layered double hydroxide; air; In 1,3,5-trimethyl-benzene; at 130 ℃; under 760.051 Torr; Reagent/catalyst;
66%
9%
With gold nanoparticles supported on a Mg-Al layered double hydroxide; air; In 1,3,5-trimethyl-benzene; at 130 ℃; under 760.051 Torr; Reagent/catalyst;
24%
25%
benzaldehyde
100-52-7

benzaldehyde

1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

Flavanone
487-26-3

Flavanone

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
With guanidine based amino graphene; In para-xylene; Reflux;
30%
30%
8%
2'-hydroxy-3-phenylpropiophenone
3516-95-8

2'-hydroxy-3-phenylpropiophenone

Flavanone
487-26-3

Flavanone

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
2'-hydroxy-3-phenylpropiophenone; With palladium(II) trifluoroacetate; copper diacetate; In dimethyl sulfoxide; at 100 ℃; for 15h; Inert atmosphere;
With hydrogenchloride; In water; dimethyl sulfoxide; ethyl acetate; at 100 ℃; for 24h; Reagent/catalyst; Inert atmosphere;
79%
10%
8%
o-hydroxyacetophenone
118-93-4,104809-67-8

o-hydroxyacetophenone

benzaldehyde
100-52-7

benzaldehyde

Flavanone
487-26-3

Flavanone

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
With gold nanoparticles supported on a Mg-Al layered double hydroxide; air; In 1,3,5-trimethyl-benzene; at 130 ℃; for 24h; under 760.051 Torr; Inert atmosphere;
24%
15%
34%
With 2C9H17N2(1+)*MoO4(2-); In hexan-1-ol; at 140 ℃; for 6h; Reagent/catalyst; Catalytic behavior;
54 %Chromat.
25 %Chromat.
18 %Chromat.
With 1-butyl-3-methylimidazolium molybdate; In hexan-1-ol; at 140 ℃; for 6h; Solvent; Catalytic behavior;
43 %Chromat.
37 %Chromat.
14 %Chromat.
2'-hydroxychalcone dibromides
39729-11-8

2'-hydroxychalcone dibromides

6-bromo-2-phenylchroman-4-one
1220531-63-4

6-bromo-2-phenylchroman-4-one

Flavanone
487-26-3

Flavanone

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
at 200 ℃; for 0.166667h;
6%
14%
14%
36%
o-hydroxyacetophenone
118-93-4,104809-67-8

o-hydroxyacetophenone

benzaldehyde
100-52-7

benzaldehyde

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
o-hydroxyacetophenone
118-93-4,104809-67-8

o-hydroxyacetophenone

benzaldehyde
100-52-7

benzaldehyde

Flavanone
487-26-3

Flavanone

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
alkali-catalysed;
65%
25%
With caesium carbonate; In ethanol; for 3h; Reflux;
58%
28%
With 1H-imidazole; 18-crown-6 ether; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; benzene; at 37 ℃; for 72h;
6.4 % Chromat.
42.4 % Chromat.
With 1H-imidazole; 18-crown-6 ether; sodium hydride; In benzene; at 37 ℃; for 72h; Product distribution; various concentrations of NaH;
31.3 % Chromat.
5.1 % Chromat.
magnesium oxide; In ethanol; for 12h; Further Variations:; Catalysts; Solvents; Product distribution; Heating;
90 % Chromat.
10 % Chromat.
With L-proline; In N,N-dimethyl-formamide; at 80 ℃; for 18h; Title compound not separated from byproducts;
With nanocrystalline mesoporous MFI-10PrTES-zeolite; at 149.84 ℃; for 8h;
With ZSM-5 (HMZ-0.28 C-0.035E) type zeolite; at 150 ℃; for 12h; Inert atmosphere; Neat (no solvent);
With b-axis-aligned mesoporous ZSM-5 zeolite H-form; at 150 ℃; for 18h; Neat (no solvent);
With mesoporous ZSM-5; at 150 ℃; for 8h; Inert atmosphere;
With sulfated zinc ferrite; In neat (no solvent); at 150 ℃; for 9h; Reagent/catalyst;
With mesoporous aluminosilicate zeolite Beta; at 135 ℃; for 18h;
With sulfonic acid functionalized mesoporous ZSM-5; at 140 ℃; for 6h; Reagent/catalyst; Catalytic behavior; Inert atmosphere;
With sodium hydroxide; In water; at 30 ℃; for 24h; Kinetics; Green chemistry;
With C7H8O2*C5H13N3; at 70 ℃; for 8h; Temperature; Solvent; Reagent/catalyst;
20 %Chromat.
77 %Chromat.
Cinnamic acid
621-82-9

Cinnamic acid

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

Flavanone
487-26-3

Flavanone

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Conditions
Conditions Yield
With cesium fluoride; In tetrahydrofuran; at 125 ℃;
54%

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  • Amadis Chemical Co., Ltd.
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  • Main Products:29
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  • Shaanxi BLOOM TECH Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-29-86470566
  • Emails:sales@bloomtechz.com
  • Main Products:79
  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:sales@chemwill.com
  • Main Products:56
  • Country:China (Mainland)
  • Leader Biochemical Group
  • Business Type:Lab/Research institutions
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