- Photo- and pH-induced transformations of flavylium cation: 'Write-lock- read-unlock-erase' cycles
-
The structural transformations of flavylium ion in aqueous solutions caused by pH jumps and photoexcitation have been investigated. At pH +). By increasing pH, the concentration of AH+ decreases and, at pH = 5, this form is no longer present. The species obtained immediately after a pH jump undergo transformation processes with pH-dependent rate constants. At pH = 5.2 and 20 °C, the final product is the uncolored trans-chalcone (C(t)). This form can be transformed by light excitation into the cis-chalcone (C(c)) isomer, which is in equilibrium with the hemiacetal form (B(2)). This mixture is relatively inert due to the existence of a kinetic barrier that slows down the back thermal isomerization of C(c) to the stable C(t) form. Such a back reaction to C(t) can be totally prevented if the irradiated solution is submitted to a pH jump to pH = 1, which transforms the photoproducts into the stable AH+ species. In basic solution, two more species were detected, namely the anionic forms C(c)- and C(t)- of the cis and trans chalcone. C(t)- is a stable, not photosensitive and luminescent species, whereas C(c)- is not stable, being converted into C(t)- in the dark. The photochemical and pH- induced transformations of the flavylium cation in the pH range 0-11 can be taken as a basis to design write-lock-read-unlockerase cycles for an optical molecular-level memory with multiple readout capacity.
- Pina, Fernando,Melo, Maria Jo?o,Maestri, Mauro,Passaniti, Paolo,Camaioni, Nadia,Balzani, Vincenzo
-
-
Read Online
- Novel triazine centred manganese based complex: A photophysical and biological studies
-
In this work, Mn(II) complex of triazine based ligand has been synthesized and characterized using various physico-chemical methods including C,H,N elemental analysis, FT-IR,1H NMR and EI-mass analysis. The synthesized compounds serve as potential photoactive material as indicated from its characteristic fluorescent properties. The ligand and its metal complex were assayed for in vitro antimicrobial activity on four bacterial strains (S. aureus, B. subtilis, E. coli and K. pneumoniae) using well-diffusion method and it was observed that metal complex showed enhanced antimicrobial activity against all tested strains as compared to ligand.
- Alphonse,Tharmaraj,Josephine, B. Avila,Teresita, V. Mary
-
-
Read Online
- Formal cycloaddition of ethyl 2-aroyl-1-chlorocyclopropanecarboxylates:facile synthesis of diversified tetrahydrocyclopropa[b]chromenes
-
Tandem reaction of ortho-hydroxy chalcone with ethyl 2-aroyl-1-chlorocyclopropanecarboxylates has been disclosed, affording facile synthesis of diversified tetrahydrocyclopropa[b]chromenes via electron-deficient cyclopropene intermediate.
- Xiong, Guoxi,Liao, Yong,Liu, Xue-Hui,Tang, Xiangying,Gong, Yuefa
-
-
Read Online
- Laser flash photolysis studies of the photo-ring-opening reaction of flav-3-en-2-ol
-
Electronic structure and photodynamics of flav-3-en-2-ol have been studied by steady-state and time-resolved absorption measurements, and by semi-empirical MO calculations. The photo-ring-opening reaction to produce 2- hydroxychalcone has been determined to be a monophotonic process with the quantum yield of 0.29. The precursor to 2-hydroxychalcone has been assigned to the ground-state enol-form by nanosecond laser flash photolysis study at room temperature and steady-state photolysis study at 77 K. The efficiency of the tautomerization from the ground-state enol-form to keto-form of 2- hydroxychalcone has been estimated to be unity. The enol-form is transformed into 2-hydroxychalcone with the rate constant of 3.2x 104 s-1 in neat acetonitrile, and this process is accelerated by protic molecules. The PM3 calculation of flav-3-en-2-ol showed that the dissociative potential surface in the first excited singlet-state is responsible for the ring-opening reaction.
- Horiuchi, Hiroaki,Yokawa, Akinobu,Okutsu, Tetsuo,Hiratsuka, Hiroshi
-
-
Read Online
- Combined 3D-QSAR and docking analysis for the design and synthesis of chalcones as potent and selective monoamine oxidase B inhibitors
-
Monoamine oxidases (MAOs) are important targets in medicinal chemistry, as their inhibition may change the levels of different neurotransmitters in the brain, and also the production of oxidative stress species. New chemical entities able to interact selectively with one of the MAO isoforms are being extensively studied, and chalcones proved to be promising molecules. In the current work, we focused our attention on the understanding of theoretical models that may predict the MAO-B activity and selectivity of new chalcones. 3D-QSAR models, in particular CoMFA and CoMSIA, and docking simulations analysis have been carried out, and their successful implementation was corroborated by studying twenty-three synthetized chalcones (151–173) based on the generated information. All the synthetized molecules proved to inhibit MAO-B, being ten out of them MAO-B potent and selective inhibitors, with IC50 against this isoform in the nanomolar range, being (E)-3-(4-hydroxyphenyl)-1-(2,2-dimethylchroman-6-yl)prop-2-en-1-one (152) the best MAO-B inhibitor (IC50 of 170 nM). Docking simulations on both MAO-A and MAO-B binding pockets, using compound 152, were carried out. Calculated affinity energy for the MAO-A was +2.3 Kcal/mol, and for the MAO-B was ?10.3 Kcal/mol, justifying the MAO-B high selectivity of these compounds. Both theoretical and experimental structure–activity relationship studies were performed, and substitution patterns were established to increase MAO-B selectivity and inhibitory efficacy. Therefore, we proved that both 3D-QSAR models and molecular docking approaches enhance the probability of finding new potent and selective MAO-B inhibitors, avoiding time-consuming and costly synthesis and biological evaluations.
- Mellado, Marco,González, César,Mella, Jaime,Aguilar, Luis F.,Vi?a, Dolores,Uriarte, Eugenio,Cuellar, Mauricio,Matos, Maria J.
-
-
- Synthesis, characterization and α-amylase and α-glucosidase inhibition studies of novel vanadyl chalcone complexes
-
A series of chalcone ligands and their corresponding vanadyl complexes of composition [VO (LI–IV)2(H2O)2]SO4 (where LI = 1,3-Diphenylprop-2-en-1-one, LII = 3-(2-Hydroxy-phenyl)-1-phenyl-propenone, LIII = 3-(3-Nitro-phenyl)-1-phenyl-propenone, LIV = 3-(4-Methoxy-phenyl)-1-phenyl-propenone) have been synthesized and characterized using various spectroscopic (Fourier-transform infrared, electrospray ionization mass, nuclear magnetic resonance, electron paramagnetic resonance, thermogravimetric analysis, vibrating sample magnetometer) and physico-analytic techniques. Antidiabetic activities of synthesized complexes along with chalcones were evaluated by performing in vitro and in silico α-amylase and α-glucosidase inhibition studies. The obtained results displayed moderate to significant inhibition activity against both the enzymes by vanadyl chalcone complexes. The most potent complexes were further investigated for the enzyme kinetic studies and displayed the mixed inhibition for both the enzymes. Further, antioxidant activity of vanadyl chalcone complexes was evaluated for their efficiency to release oxidative stress using 2,2-diphenyl-1-picryl-hydrazyl-hydrate assay, and two complexes (Complexes 2 and 4) have demonstrated remarkable antioxidant activity. All the complexes were found to possess promising antidiabetic and antioxidant potential.
- Kaur, Mandeep,Kaushal, Raj
-
-
- Highly enantioselective addition of aliphatic aldehydes to 2-hydroxychalcone enabled by cooperative organocatalysts
-
Herein, we developed an enantioselective addition of aliphatic aldehydes to 2-hydroxychalcone promoted by cooperative organocatalysts, giving access to hybrid flavonoids in excellent enantioselectivities. This reaction took advantage of cycloisomerization of 2-hydroxychalcone to form a transient flavylium under the irradiation of 24 W CFL, which was trapped by the in situ generated chiral enamine intermediate. The synergistic action of chiral phosphoric acid secured the excellent outcome of this reaction by ion-pairing with the transient flavylium.
- Chen, Le,Chen, Lu,Gao, Yu-Qi,Hou, Yi,Hu, Jiadong,Wen, Wen,Xie, Weiqing,Xu, Dongyang
-
supporting information
p. 10018 - 10021
(2020/09/15)
-
- Synthesis of sulfonamides bearing 1,3,5-triarylpyrazoline and 4-thiazolidinone moieties as novel antimicrobial agents
-
Two series of sulfonamides were synthesized from 4-hydrazinylben-zenesulfonamide as the key starting material. 1,3,5-Triarylpyrazoline sulfonamides (2a-i) were obtained by cyclocondensation of various chalcones in 53-64 % yields, while 4-thiazolidinone derivatives (4a-e) were synthesized by cyclocondensation between mercaptoacetic acid and different phenylhydrazones in 43-62 % yields. The synthesized compounds were characterized based on FTIR, 1H-NMR, 13C-NMR and HRMS data. The sulfonamides were evaluated for their in vitro antimicrobial activities against four bacterial strains (E. coli, P. aeruginosa, B. subtillis and S aureus), two filamentous fungal strains (A. Niger and F. oxysporum) and two yeast strains (C. albicans and S. cerevisiae). Seven pyrazolines, 2a-c and 2e-h, exhibited significant inhibition of different microbial strains. Among them, compound 2b displayed good antifungal activity against A. Niger (MIC value at 12.5 μg mL-1) over the reference drug.
- Thach, Thi-Dan,Le, Thi Tuong-Vi,Nguyen, Huu Thien-An,Dang, Chi-Hien,Dang, Van-Su,Nguyen, Thanh-Danh
-
p. 158 - 162
(2020/05/08)
-
- Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies
-
In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.
- Bhoi, Manoj N.,Borad, Mayuri A.,Jethava, Divya J.,Pandya, Himanshu A.,Patel, Chirag N.,Patel, Hitesh D.
-
-
- Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds
-
A series of 16 chalcone compounds were synthesized by Claisen-Schmidt condensation of various aldehydes with acetophenone using KOH as a base in ethanol. The reaction affords the desired products in good yields. Then all the 16 compounds were converted into pyrazoles by treating with hydrazine hydrate in ethanol under reflux condition. Both chalcones and pyrazoles were screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and antifungal (Aspergillus flavus, Chrysosporium keratinophilum and Candida albicans) activity. Biological activities of these compounds were compared with those of commercially available antibiotic ampicillin and antifungal agent miconazole. Pyrazoles were found to be most active and effective than corresponding chalcones for antimicrobial activity. Out of the 7 pyrazole compounds tested for antibacterial and antifungal activity, 5 compounds, 4h, 4j, 4l, 4m and 4n are turned out to be potent antimicrobial agents. Therefore these derivatives could serve as a highly promising molecules for further development.
- Nagendra Chowdary,Umashankara,Dinesh,Girish,Ramesha Baba
-
-
- One-Pot Allylation-Intramolecular Vinylogous Michael Addition-Isomerization Cascade of o-Hydroxycinnamates and Congeners: Synthesis of Substituted Benzofuran Derivatives
-
A unique intramolecular vinylogous Michael addition leading to the synthesis of heterocycles has been disclosed. Base-promoted one-pot sequential O-allylation of o-hydroxy-cinnamates or -cinnamonitrile or -chalcones with γ-bromocrotonates followed by an intramolecular conjugate addition of vinylogous Michael donors resulted in the formation of highly substituted benzofuran derivatives in good to excellent yields. The intramolecular event followed by two [1,3]-H shifts leading to aromatization appears to be the key to the success of this unprecedented transformation.
- Harish, Battu,Subbireddy, Manyam,Obulesu, Owk,Suresh, Surisetti
-
supporting information
(2019/03/19)
-
- Design, synthesis, and carbonic anhydrase inhibition activity of benzenesulfonamide-linked novel pyrazoline derivatives
-
Carbonic anhydrases (CA, EC 4.2.1.1) are Zinc metalloenzymes and are present throughout most living organisms. Among the catalytically active isoforms are the cytosolic CA I and II, and tumor-associated CA IX and CA XII. The carbonic anhydrase (CA) inhibitory activities of newly synthesized pyrazoline-linked benzenesulfonamides 18–33 against human CA (hCA) isoforms I, II, IX, and XII were measured and compared with that of acetazolamide (AAZ), a standard inhibitor. Potent inhibitory activity against hCA I was exerted by compounds 18–25, with inhibition constant (KI) values of 87.8–244.1 nM, which were greater than that of AAZ (KI, 250.0 nM). Compounds 19, 21, 22, 29, 30, and 32 were proven to have inhibitory activities against hCA IX with KI values (5.5–37.0 nM) that were more effective than or nearly equal to that of AAZ (KI, 25.0 nM). Compounds 20–22, and 30 exerted potent inhibitory activities (KIs, 7.1–10.1 nM) against hCA XII, in comparison with AAZ (KI, 5.7 nM).
- Abdel-Aziz, Alaa A.-M.,El-Azab, Adel S.,Bua, Silvia,Nocentini, Alessio,Abu El-Enin, Mohamed A.,Alanazi, Mohammed M.,AlSaif, Nawaf A.,Hefnawy, Mohamed M.,Supuran, Claudiu T.
-
p. 425 - 431
(2019/03/27)
-
- Design, Synthesis, Drug-Likeness Studies and Bio-Evaluation of Some New Chalconeimines
-
Newly designed chalconeimines were synthesized, characterized and evaluated for their in vitro antioxidant and antibacterial effectiveness. Results of antioxidant activity assay reveal that all the tested compounds possess good to moderate antioxidant activity which is lower in comparison to that of a standard drug (gallic acid). On the other hand, all the synthesized compounds were found to exhibit a considerably wider spectrum of antibacterial activity, but it was also narrower in comparison to that of a standard drug (ciprofloxacin). Elucidation of structure—activity relationships revealed that electron donating groups (-OH, -OCH3) contribute more to antioxidant potency, whereas electron withdrawing groups (-Cl) impart better antibacterial effectiveness. Moreover, results of drug-likeness studies indicate that a reasonable correlation exists between the drug-like properties and antioxidant activity of the synthesized chalconeimines.
- Rudrapal, Mithun,Sowmya, Mullapudi P. K.
-
p. 814 - 821
(2019/12/23)
-
- Design, Synthesis, and Biological Evaluation of Pyrazoline-Based Hydroxamic Acid Derivatives as Aminopeptidase N (APN) Inhibitors
-
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
-
supporting information
p. 431 - 436
(2018/02/21)
-
- Pyrazoline aminopeptidase N inhibitor and its preparation method and application (by machine translation)
-
The invention discloses a pyrazoline aminopeptidase N inhibitor and its preparation method and application. The invention relates to compounds having the general formula (I) or (II) the structure of the shown. The invention also provides a preparation method of the cardiovascular diseases and in preparation for preventing or treating the abnormal activity of aminopeptidase diseases associated with application of the medicament. (by machine translation)
- -
-
Paragraph 0147; 0148
(2018/05/16)
-
- Chalcones and their pyrazine analogs: synthesis, inhibition of aldose reductase, antioxidant activity, and molecular docking study
-
Abstract: Chalcones and their pyrazine analogs synthesized by Claisen–Schmidt condensation were tested for inhibition of aldose reductase, which is the key enzyme in the development of secondary diabetic complications. The most active compounds exerted IC50 values within the micromolar scale, and their interactions with the enzyme were described in a molecular docking study. Antioxidant activity of several representative compounds was explored in DPPH (2,2-diphenyl-1-picrylhydrazyl) assay, revealing significant scavenging for 4-hydroxy-substituted derivatives endowed with electron-donating methoxy substituent in position 3 of the ring B. To conclude, the novel chalcones hydroxylated and methoxylated in the B-ring and their pyrazine analogs exhibited significant aldose reductase inhibition activity, albeit lower in comparison with the reference epalrestat. Medium antioxidant activity (not exceeding the antioxidant efficacy of the standard Trolox) was shown by the representative compounds tested.
- Kucerova-Chlupacova, Marta,Dosedel, Martin,Kunes, Jiri,Soltesova-Prnova, Marta,Majekova, Magdalena,Stefek, Milan
-
p. 921 - 929
(2018/02/26)
-
- Synthesis and antimicrobial activity of some 5-chloro-3-phenyl-1H-indole-2-carbonyl azide derivatives
-
In the present investigations, a series of new 6-substituted-3-(5-chloro-3-phenyl-lJ?-indole-2yl)-3,4-dihydro-4-substituted-4-substituted-phenacyl-2H-l,3-benzoxazin-2-one 7a-f have been synthesized by two methods making use of 5-chloro-3-phenyl-l/H-ndole-2-carbonyl azide 2 and chalcones 5a-f. In one method, compound 2 on reaction with chalcones 5a-f in presence of triethylamine in dry benzene yields respective open chain carbamates 6a-f, followed by reaction with catalytic amount of potassium hydroxide in dry benzene under reflux condition to afford compounds 7a-f. In another method, compound 5a-f on reaction with compound 2 using dry benzene in presence of catalytic amount of potassium hydroxide under reflux conditions afford cyclized products 7a-f in good yield. Structures of the all the newly synthesized compounds have been confirmed by spectral data. All these compounds have been screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, antifungal activity against Aspergillus Niger and Candida albicans and antituberculosis activity against Mycobacterium tuberculosis (H37RV).
- Basavarajaiah,Mramyunjayaswamy
-
p. 390 - 399
(2019/05/21)
-
- Exploitation of new chalcones and 4H-chromenes as agents for cancer treatment
-
Chalcone and chromene derivatives were synthesized in good yield through simple and effective reactions using innocuous solvents such as water and ethanol and high yielding aldol condensations. Generally, the reactions were performed at room temperature, leading to the isolation of highly pure compounds. These compounds were tested on breast cancer cells (MCF-7 and Hs578T) and breast non-neoplastic cells (MCF-10A). After determination of IC50 value, specific assays were performed to analyze the potential of these compounds, and those bearing halogenated substituents presented enhanced activity comparing to methoxyl or methyl groups. More specifically, the bromine atom was often present in the bioactive molecules that proceeded to the final assays and showed to be promising candidates for further studies. The selected chromene acted as a cell migration inhibitory agent and triggered regulated cell death associated with G2/M cell-arrest and microtubule destabilization. For chalcones, the results suggest an anti-proliferative activity. Also, results for combination-therapy potentiated the antitumor effect of doxorubicin and reduced cytotoxicity in MCF-10A cells.
- Pontes, Olívia,Costa, Marta,Santos, Filipa,Sampaio-Marques, Belém,Dias, Tatiana,Ludovico, Paula,Baltazar, Fátima,Proen?a, Fernanda
-
p. 101 - 114
(2018/08/06)
-
- Design, synthesis and biological evaluation of tricyclic pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one scaffolds as selective BuChE inhibitors
-
Based on the structural analysis of tricyclic scaffolds as butyrylcholinesterase (BuChE) inhibitors, a series of pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one derivatives were designed, synthesized and evaluated for their acetylcholinesterase (AChE) and BuChE inhibitory activity. Compounds with 5-carbonyl and 7- or/and 9-halogen substitutions showed potential BuChE inhibitory activity, among which compounds 6a, 6c and 6g showed the best BuChE inhibition (IC50 = 1.06, 1.63 and 1.63 μM, respectively). The structure–activity relationship showed that the 5-carbonyl and halogen substituents significantly influenced BuChE activity. Compounds 6a and 6g were found nontoxic, lipophilic and exhibited remarkable neuroprotective activity and mixed-type inhibition against BuChE (Ki = 7.46 and 3.09 μM, respectively). Docking studies revealed that compound 6a can be accommodated into BuChE via five hydrogen bonds, one Pi–Sigma interaction and three Pi–Alkyl interactions.
- Qiu, Guo-Liang,He, Shao-Sheng,Chen, Shi-Chao,Li, Bo,Wu, Hui-Hui,Zhang, Jing,Tang, Wen-Jian
-
p. 1506 - 1515
(2018/10/15)
-
- Dihydropyrazothiazole derivatives as potential MMP-2/MMP-8 inhibitors for cancer therapy
-
MMP-2/MMP-8 is established as one of the most important metalloenzymes for targeting cancer. A series of dihydropyrazothiazole derivatives (E1–E18) bearing a salicylaldehyde group linked to Pyrazole ring were designed, synthesized, and evaluated for their pharmacological activity as MMP-2/MMP-8 inhibitors. Among them, compound E17 exhibited most potent inhibitory activity (IC50 = 2.80 μM for MMP-2 and IC50 = 5.6 μM for MMP-8), compared to the positive drug CMT-1 (IC50 = 1.29 μM). Compounds (E1–E18) were scrutinized by CoMFA and CoMSIA techniques of Three-dimensional quant. structure-activity relationship (3D-QSAR), as well as a docking simulation. Moreover, treatment with compound E4 could induce MCF-7 cell apoptosis. Overall, the biological profile of E1–E18 may provide a research basis for the development of new agents against cancer.
- Wang, Zhong-Chang,Shen, Fa-Qian,Yang, Meng-Ru,You, Ling-Xia,Chen, Li-Zhi,Zhu, Hai-Liang,Lu, Ya-Dong,Kong, Fan-Lei,Wang, Ming-Hua
-
supporting information
p. 3816 - 3821
(2018/10/20)
-
- Synthesis of Functionalized Chromene and Chroman Derivatives via Cesium Carbonate Promoted Formal [4 + 2] Annulation of 2′-Hydroxychalcones with Allenoates
-
A new strategy has been established for the synthesis of functionalized chromene and chroman derivatives via a Cs2CO3-catalyzed domino addition of 2′-hydroxychalcone derivatives with allenoates, which can serve as a general avenue for the construction of multireplaced chromene derivatives. Chemoselectivity of this synthesis was found to depend on substituents on substrates. Good to excellent yields were achieved under simple and mild conditions at room temperature.
- Rouh, Hossein,Liu, Yangxue,Katakam, Nandakumar,Pham, Lilian,Zhu, Yi-Long,Li, Guigen
-
p. 15372 - 15379
(2019/01/04)
-
- Design, in silico and in?vitro evaluation of curcumin analogues against Plasmodium falciparum
-
The polyphenolic compound curcumin has been reported for its antimalarial properties in various scientific studies. Plasmodium falciparum ATP6, the parasite orthologue of mammalian sarcoplasmic Ca2+ ATPase (SERCA) has been identified as a key molecular target of both artemisinin and curcumin. The work was thereby undertaken to study the anti-malarial properties of two different series of curcumin analogues based on their docking interactions with PfATP6 and correlating the results with their anti-malarial activity. The compounds were designed retaining similar functional groups as that of the parent curcumin nucleus while incorporating changes in the carbon chain length, unsaturated groups and the number of ketone groups. The compounds (1E, 4E)-1,5-bis(4-methylphenyl)penta-1,4-dien-3-one (CD-9), (1E, 4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one (CD-8) and (E)-1,3-bis(4-hydroxylphenyl)prop-2-en-1-one (CD-1) showed IC50 values of 1.642?μM, 1.764?μM and 2.59?μM in 3D7 strain and 3.039?μM, 7.40?μM and 11.3?μM in RKL-2 strain respectively. Detailed structure-activity relationship studies of the compounds showed that CD-9 and CD-8 had a common hydrophobic interaction with the residue Leu268 of the PfATP6 protein and has been postulated through our study to be the reason for their antimalarial activity as seen after corroborating the results with the in?vitro study. The study provided valuable insight about the ligand-protein interaction of the various functional groups of curcumin and its analogues against the PfATP6 protein and their importance in imparting antimalarial action.
- Dohutia, Chandrajit,Chetia, Dipak,Gogoi, Kabita,Sarma, Kishore
-
-
- Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia
-
A series of hydroxychalcone derivatives have been designed, synthesized and evaluated for human xanthine oxidase (XO) inhibitory activity. Most of the tested compounds acted moderate XO inhibition with IC50 values in the micromolar rang. Molecular docking and kinetic studies have been performed to explain the binding modes of XO with the selected compounds. In addition, in vitro antioxidant screening results indicated that some of the hydroxychalcones possessed good anti-free radical activities. Furthermore, the preferred compounds 16 and 18 were able to significantly inhibit hepatic xanthine oxidase activity and reduced serum uric acid level of hyperuricemic mice in vivo. In summary, compounds 16 and 18 with balanced activities of antioxidant, XO inhibition and serum uric acid reduction, which are promising candidates for the treatment of hyperuricemia and gout.
- Xie, Zhaodi,Luo, Xiaoting,Zou, Zhuan,Zhang, Xiao,Huang, Feifei,Li, Ruishan,Liao, Shijie,Liu, Yun
-
supporting information
p. 3602 - 3606
(2017/07/07)
-
- Synthesis and biological evaluation of α-methyl-chalcone for anti-cervical cancer activity
-
A series of 31 chalcones were synthesized and evaluated for anti-proliferative activity against the human cervical cancer cell lines (HeLa and SiHa). Compound 19, (E)-1-(2,4-dihydroxyphenyl)-3-(4-(dimethylamino) phenyl)-2-methylprop-2-en-1-one was found to be an effective anti-proliferative agent in HeLa and SiHa cells (IC50 = 0.035 μM). Compound 19 increased the percentage of apoptosis in a dose-dependent manner, as measured by Annexin V-FITC (fluorescein isothiocyanate)/(propidium iodide) PI staining. Molecular modeling studies of compound 19 showed that the most potent structure was docked at the yeast 20 S proteasome binding site (Protein Data Bank code-3E47) and was stabilized in the cavity by various hydrophobic and hydrogen bonding interactions.
- Ren, Bing-zhao,Ablise, Mourboul,Yang, Xu-chao,Liao, Bo-er,Yang, Zheng
-
p. 1871 - 1883
(2017/08/03)
-
- Synthesis of 6,12-Methanobenzo[d]pyrano[3,4-g][1,3]dioxocin-1(12H)-ones and Study of Their Interaction with DNA and β-Lactoglobulin
-
An efficient synthesis of 6,12-methanobenzo[d]pyrano[3,4-g][1,3]dioxocin-1(12H)-ones, a new class of 2,8-dioxabicyclo[3.3.1]nonanes, starting from 2-hydroxychalcones or their analogues and 4-hydroxy-6-methyl-2H-pyran-2-one has been achieved by use of amberlyst-15, a sulfonated polystyrene resin, as a recyclable heterogeneous catalyst. The methodology involves a domino sequence of Michael addition and two-stage heterocyclization. Among the synthesized products, two show significant ct-DNA-binding properties and all show strong binding with the carrier protein β-lactoglobulin (β-lg). A study of antibacterial properties conducted on two bacterial species by using four compounds showed that two of them are moderately active.
- Sepay, Nayim,Guha, Chayan,Maity, Sanhita,Mallik, Asok K.
-
p. 6013 - 6022
(2017/11/14)
-
- Synthesis of several types of 2,8-dioxabicyclo[3.3.1]nonanes using amberlyst-15 as an efficient recyclable heterogeneous catalyst
-
A facile synthesis of 2,8-dioxabicyclo[3.3.1]nonane derivatives starting from simple molecules, such as 2-hydroxychalcones as one component and dimedone, 4-hydroxycoumarin, 2-hydroxynaphthoquinone, 2-naphthol or 1-naphthol, as the other has been achieved by use of amberlyst-15, a sulfonated polystyrene resin, as a recyclable heterogeneous catalyst. The methodology involves a domino sequence of Michael addition and two-stage cyclisation.
- Samanta, Swati,Sepay, Nayim,Mallik, Sumitava,Mondal, Rina,Rahaman Molla, Mosidur,Mallik, Asok K.
-
supporting information
p. 2195 - 2201
(2017/11/15)
-
- Enantioselective synthesis of 2,3-disubstituted: Trans -2,3-dihydrobenzofurans using a Br?nsted base/thiourea bifunctional catalyst
-
The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96 : 4 dr, 95 : 5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pro-nucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.
- Barrios Antúnez, Diego-Javier,Greenhalgh, Mark D.,Fallan, Charlene,Slawin, Alexandra M. Z.,Smith, Andrew D.
-
supporting information
p. 7268 - 7274
(2016/08/05)
-
- Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers
-
In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono- and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones' effects to rescue neurons subjected to ROS-induced stress created by the addition of β-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class.
- Hofmann, Emily,Webster, Jonathan,Do, Thuy,Kline, Reid,Snider, Lindsey,Hauser, Quintin,Higginbottom, Grace,Campbell, Austin,Ma, Lili,Paula, Stefan
-
p. 578 - 587
(2016/02/09)
-
- Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect
-
2-Amino-3-nitrile-chromenes with potential antitumor activity were constructed by a novel catalytic system. In combination with α-naphthol, quinine could effectively promote the Michael-cyclization process of malononitrile with functionalized chalcones in high yields and moderate to good enantioselectivity (up to 84% ee). It is notable that the enantioselectivity could be greatly improved when α-naphthol was employed as additive.
- Zheng, Yuan-Qin,Luan, Chun-Feng,Wang, Zhi-Jing,Yao, Yong-Qi,Shi, Zhi-Chuan,Li, Xue-Feng,Zhao, Zhi-Gang,Chen, Feng
-
supporting information
p. 25 - 30
(2016/01/25)
-
- Facile synthesis of 4H-chromene derivatives via base-mediated annulation of orffro-hydroxychalcones and 2-bromoallyl sulfones
-
The cesium carbonate-mediated reaction of 2-bromoallyl sulfones and ortho-hydroxychalcones furnished 3-arylsulfonyl-4H-chromene derivatives in 58-67% yield (18 examples). 2-Bromoallyl sulfones functioned as synthetic surrogates for allenyl sulfones in the reaction.
- Thadkapally, Srinivas,Kunjachan, Athira C.,Menon, Rajeev S.
-
-
- Novel tricyclic pyrazolo[1,5-d][1,4]benzoxazepin-5(6H)-one: Design, synthesis, model and use as hMAO-B inhibitors
-
Based on our recently reported selective hMAO-A inhibitors, on which, the intramolecular cyclization led to a very interesting change of isoform selectivity. A series of selective hMAO-B inhibitors (3a-3u) with novel scaffold of tricyclic pyrazolo[1,5-d][1,4]benzoxazepin-5(6H)-one were designed and synthesized. Compound 3u (IC50 = 221 nM) exhibited the best inhibitory activity and isoform selectivity against hMAO-B, superior to selegiline (IC50 = 321 nM), which is a commercial selective hMAO-B inhibitor used to Parkinson's disease. Modeling study indicated that the selectivity of our compounds to hMAO-B is determined by at least two residues, i.e., Ile 199 and Cys 172 (or corresponded Phe 208 and Asn 181 of hMAO-A). These data support further studies to assess rational design of more efficiently selective hMAO-B inhibitors.
- Chen, Rui,Xiao, Jie,Ni, Yong,Xu, Han-Fei,Zheng, Min,Tong, Xu,Zhang, Tong-Tian,Liao, Chenzhong,Tang, Wen-Jian
-
p. 1741 - 1748
(2016/04/05)
-
- Synthesis of some novel substituted phenylisoxazol phenoxy 2-methylpropanoic acids and there in vivo hypolipidemic activity
-
The novel series of phenylisoxazol phenoxy 2-methylpropanoic acid derivatives were synthesized and evaluated for their in vivo hypolipidemic activity by triton WR-1339-induced hyperlipidemia in rats. The newly synthesized compounds 5a and 5i showed significant decrease in the serum TCH, TG, LDL and VLDL along with an increase in serum HDL levels as compared to standard drug Fenofibrate. The treated groups also showed significant decrease in the atherogenic index, TC:HDL risk ratios compared to cholesterol-induced hyperlipidemic control group. These molecules indeed have the potential to be developed as antihypolipidemic molecules.
- Mokale, Santosh N.,Dube, Pritam N.,Nevase, Manjusha C.,Sakle, Nikhil S.,Shelke, Vishakha R.,Bhavale, Swati A.,Begum, Afreen
-
p. 422 - 428
(2016/02/19)
-
- QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase
-
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.
-
p. 2133 - 2142
(2016/10/25)
-
- Catalyzed Claisen-Schmidt reaction by protonated aluminate mesoporous silica nanomaterial focused on the (E)-chalcone synthesis as a biologically active compound
-
The mesoporous silica structure (MSN) was synthesized using the sol-gel method followed by aluminum grafting and protonation and was then denoted as HAlMSN (Si/Al = 18.9). N2 physisorption confirmed the mesoporous structure with a pore diameter of 3.38 nm. 27Al NMR showed the presence of framework and extra-framework aluminum structures, which led to the formation of strong Lewis and Br?nsted acidic sites. HAlMSN catalyzed the synthesis of (E)-chalcones through the Claisen-Schmidt reaction. Chalcone derivatives have been applied as biologically active compounds with anti-cancer, anti-inflammatory and diuretic pharmacological activities. The products were obtained via reactions on the protonic acid sites of HAlMSN. The significant advantages of this reaction are high yield, easy work up, short reaction time and also compatibility with various organic solvents. The products were obtained in an excellent conversion of 97% at 298 K. The results show that the electron donating substituents exhibit higher conversion in comparison to electron withdrawing substituents. The stability of the catalyst was investigated by reusing it five times for (E)-chalcone production and there was only a slight decrease in its catalytic activity. The highest product of (E)-chalcone was observed with a 1:2 molar ratio of benzaldehyde/acetophenone. A comparative study in chalcone synthesis using the heterogeneous catalysts demonstrated that HAlMSN has a significantly high activity at low temperature.
- Sazegar, Mohammad Reza,Mahmoudian, Shaya,Mahmoudi, Ali,Triwahyono, Sugeng,Jalil, Aishah Abdul,Mukti, Rino R.,Nazirah Kamarudin, Nur H.,Ghoreishi, Monir K.
-
p. 11023 - 11031
(2016/02/05)
-
- Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst
-
A highly enantioselective synthesis of chiral chroman derivatives via an oxa-Michael-Michael cascade reaction has been developed using a bifunctional thiourea organocatalyst. The products were obtained with excellent enantioselectivities (up to >99%), good yields (up to 95%), and diastereoselectivities (up to 5:1).
- Saha, Prasenjit,Biswas, Arnab,Molleti, Nagaraju,Singh, Vinod K.
-
p. 11115 - 11122
(2015/11/18)
-
- Synthesis and evaluation of novel prenylated chalcone derivatives as anti-leishmanial and anti-trypanosomal compounds
-
Abstract Chalcones form a class of compounds that belong to the flavonoid family and are widely distributed in plants. Their simple structure and the ease of preparation make chalcones attractive scaffolds for the synthesis of a large number of derivatives enabling the evaluation of the effects of different functional groups on biological activities. In this Letter, we report the successful synthesis of a series of novel prenylated chalcones via Claisen-Schmidt condensation and the evaluation of their effect on the viability of the Trypanosomatidae parasites Leishmania amazonensis, Leishmania infantum and Trypanosoma cruzi.
- Passalacqua, Thais Gaban,Dutra, Luiz Antonio,De Almeida, Letícia,Velásquez, Angela Maria Arenas,Torres Esteves, Fabio Aurelio,Yamasaki, Paulo Renato,Dos Santos Bastos, Mariana,Regasini, Luis Octavio,Michels, Paul A.M.,Da Silva Bolzani, Vanderlan,Graminha, Marcia A.S.
-
supporting information
p. 3342 - 3345
(2015/07/08)
-
- The design, synthesis, in vitro biological evaluation and molecular modeling of novel benzenesulfonate derivatives bearing chalcone moieties as potent anti-microtubulin polymerization agents
-
A series of novel 3,4-dimethoxylbenzenesulfonate derivatives containing a chalcone structure were synthesized and evaluated for their anti-proliferative activities against HepG2, HCT-116, MCF-7 and HeLa cell lines, as well as the effects of compound 10b on mitotic arrest and cell cycle of MCF-7 carcinoma cell line. Most importantly, the results of DAPI staining under co-focal microscope justified that compound 10b functioned even at relatively low concentration. The analogues showed a potent bio-activity towards tumor cells with IC50 values at nano-mole class, compared with those of positive control drug Colchicine, whose IC50 were 150.4 nM for MCF-7, 123.9 nM for HepG2, 125.4 nM for HCT-116 and 131.4 nM for HeLa cells. Also, a molecular docking modeling was utilized to reveal the binding mode of derivatives and microtubule. Among all the synthesized compounds, compound 10b stands out as IC50 values against all the selected cell lines were at average 80 nM (in which the values against MCF-7 and HepG2 were similar; about 79.2 nM). In this research, we gave strong evidence upon the optimized stratagem for ligands targeting the colchicine-binding site on microtubules, explaining the attribution that the analogues were designed upon the structure of chalcone and combretastatin A-4.
- Shen, Yu-Ning,Lin, Lin,Qiu, Han-Yue,Zou, Wen-Yan,Qian, Yong,Zhu, Hai-Liang
-
p. 23767 - 23777
(2015/04/14)
-
- Intramolecular oxidative coupling: I2/TBHP/NaN3-mediated synthesis of benzofuran derivatives
-
A novel intramolecular oxidative coupling reaction has been established to prepare benzofuran derivatives via direct C(sp2)-H functionalization for the formation of C-O bond. This transformation is mediated by I2/TBHP/NaN3 under metal-free conditions and a catalytic amount of NaN3 plays a crucial role in the reaction. Furthermore, the reaction tolerates a broad substrate scope with average to excellent yields.
- Xu, Wengang,Li, Qingcui,Cao, Chuanpeng,Zhang, Fanglin,Zheng, Hua
-
supporting information
p. 6158 - 6161
(2015/06/08)
-
- Synthesis, biological evaluation, quantitative-SAR and docking studies of novel chalcone derivatives as antibacterial and antioxidant agents
-
In the present study, a series of chalcone derivatives including 17 new compounds were synthesised; their antibacterial activities against eleven bacteria, and their free radical-scavenging activities using DPPH were evaluated. All compounds showed significant antibacterial activities against both Grampositive and Gram-negative bacteria. In particular, compound IIIf strongly inhibited Staphylococcus aureus (JMC 2151) and Enterococcus faecalis (CARS 2011-012) with MIC values of 6.25 μg mL-1 and 12.5 μg mL-1, respectively, which are comparable to that of the standard antibiotic, nalidixic acid. Compound IIIg also inhibited S. aureus with a MIC value similar to that of nalidixic acid (6.25 μg mL-1). Furthermore, like nalidixic acid (MIC value of 25 μg mL-1), compounds IIIa, IIIc and IIId inhibited Listeria monocytogenes (ATCC 43256) with MIC values of 25 μg mL-1, 12.5 μg mL-1 and 25 μg mL-1, respectively. Quantitative structure-activity relationship (Q-SAR) studies using physicochemical calculations indicated that the antibacterial activities of chalcone derivatives correlated well with predicted physicochemical parameters (logP and PSA). Docking simulation by positioning the most active compound IIIf in the active site of the penicillin-binding protein (PBP-1b) of S. aureus was performed to explore the feasible binding mode. Furthermore, most of the compounds synthesised exhibited significant DPPH radical-scavenging activity, although compounds IIc and IIIc exhibited the greatest antioxidant activity with IC50 values of 1.68 μM and 1.44 μM, respectively, comparable to that of the standard antioxidant, ascorbic acid (1.03 μM).
- Alam, Mohammad Sayed,Rahman, S. M. Mostafizur,Lee, Dong-Ung
-
p. 1118 - 1129
(2015/06/08)
-
- Design and synthesis of novel 2-pyrazoline-1-ethanone derivatives as selective MAO inhibitors
-
Thirty seven novel 2-pyrazoline-1-ethanone derivatives were designed, synthesized and evaluated as selective hMAO inhibitors. Among them, compounds 7h (IC50 = 2.40 μM) and 12c (IC50 = 2.00 μM) exhibited best inhibitory activity and selectivity against hMAO-A, surpassing that of the positive control Clorgyline (IC50 = 2.76 μM). Based on selective activity of hMAO-A, SAR analysis showed that the order of N1 substituent contribution was bromo (3) > piperidinyl (4) > morpholinyl (5) > imidazolyl (6), and compounds with electron-withdrawing substituents (-F, -Cl) at C3 or C5 phenyl ring of 2-pyrazoline nucleus dedicated stronger MAO-A inhibitory activity. Molecular docking showed that compounds 7h and 12c were nicely bound to hMAO-A via two hydrogen bonds (SER209, GLU216), one Pi-Pi interaction and three hydrogen bonds (SER209, GLU216, TYR69), one Sigma-Pi interaction, respectively. In addition, the substituent at C3 position of 2-pyrazoline with the N1 acetyl has little effect on MAO-A inhibitory activity. These data support further studies to assess rational design of more efficiently selective hMAO inhibitors in the future.
- Tong, Xu,Chen, Rui,Zhang, Tong-Tian,Han, Yan,Tang, Wen-Jian,Liu, Xin-Hua
-
p. 515 - 525
(2015/01/30)
-
- ZrCl4-catalysed synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridine derivatives
-
In the presence of a catalytic amount of zirconium(IV) chloride, an efficient synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridines has been developed by the reaction 2-hydroxychalcones with 3-methyl-1-phenyl-1H-pyrazol-5-amine in refluxing ethanol. All these novel compounds have been characterised by 1H NMR, 13C NMR, HRMS, IR spectra and X-ray crystallographic analysis.
- Liu, Meilin,Yin, Guodong
-
p. 236 - 266
(2015/06/02)
-
- Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans
-
Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.
- Shang, Xuyang,Zhou, Xiaomeng,Zhang, Wei,Wan, Changfeng,Chen, Junmin
-
p. 8187 - 8193
(2015/12/30)
-
- Synthesis, biological evaluation, and docking of dihydropyrazole sulfonamide containing 2-hydroxyphenyl moiety: A series of novel MMP-2 inhibitors
-
In this study, we synthesized a series of dihydropyrazole sulfonamide derivatives containing 2-hydroxyphenyl moiety as antitumor agents to target the matrix metalloproteinase-2 (MMP-2). All of the synthesized compounds were examined by bioactivity assays, in which compound 4c turned out as a potential antagonist of MMP-2 along with potent anticancer activity against four tumor cell lines. Structure-activity relationship analysis was also performed to examine how structural changes impacted the bioactivity. Suggested to be caused by the induction of apoptosis, the antitumor mechanism of 4c was further confirmed by PI combining with annexin V-FITC staining assay using flow cytometry analysis. These new findings along with molecular docking observations suggested that compound 4c could be developed as a potential anticancer agent. A series of dihydropyrazole sulfonamide derivatives containing 2-hydroxyphenyl moiety were designed and synthesized as antitumor agent to target the matrix metalloproteinase-2 (MMP-2). All of the synthesized compounds were examined by bioactivity assays, and structure-activity relationship analysis was also performed to discuss how structural changes could impact the bioactivity.
- Wang, Peng-Fei,Qiu, Han-Yue,Baloch, Shahla Karim,Gong, Hai-Bin,Wang, Zhong-Chang,Zhu, Hai-Liang
-
p. 1405 - 1410
(2016/02/05)
-
- Synthesis and screening of antimicrobial activity of novel pyrrolylpyrazole derivatives
-
Novel pyrrolyl-pyrazole derivatives (5a-k) were synthesized by reacting substituted chalcones (3a-k) and 4-pyrrol-1-yl benzoic acid hydrazide (4) in ethanol. Purity of newly synthesized compounds were confirmed by TLC and melting point. The structures of all newly synthesized compounds were confirmed by spectral study such as IR, 1H NMR and Mass spectroscopy. The title compounds were screened for their antibacterial and antitubercular activities.
- Hallikeri,Joshi, Shrinivas D.,Kumar, Devendra,Kulkarni,Selvam, Theivendren Paneer
-
p. 261 - 264
(2019/01/21)
-
- Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure-activity relationship analysis and regulation of apoptotic proteins
-
In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-lymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, Bcl-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, sTNF-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated.
- Mai, Chun Wai,Yaeghoobi, Marzieh,Abd-Rahman, Noorsaadah,Kang, Yew Beng,Pichika, Mallikarjuna Rao
-
supporting information
p. 378 - 387
(2014/04/17)
-
- Synthesis and evaluation of chalcone derivatives as inhibitors of neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species
-
Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti-inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol- and lucigenin-based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4-methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators. Chalcone derivatives were synthesised and evaluated for their inhibitory effects on PMNs chemotaxis, phagocytosis and intracellular and extracellular ROS productions. It was observed that phenyl-4-methylaminoethanol and dimethoxy substituents contributed to these effects.
- Bukhari, Syed N. A.,Tajuddin, Yasmin,Benedict, Vannessa J.,Lam, Kok W.,Jantan, Ibrahim,Jalil, Juriyati,Jasamai, Malina
-
p. 198 - 206
(2014/02/14)
-
- Nano titania-supported sulfonic acid: An efficient and reusable catalyst for a range of organic reactions under solvent free conditions
-
Nano titania-supported sulfonic acid (n-TSA) has been easily prepared from the reaction of nano titania (titanium oxide) with chlorosulfonic acid as sulfonating agent and characterized by the FT-IR spectroscopy, scanning electron microscopy (SEM), X-ray diffraction (XRD) and thermal gravimetric analysis (TGA). The catalytic activity of n-TSA was investigated in the synthesis of important organic derivatives such as pyrimidones, benzothiazoles and chalcones. All of the reactions are very fast and the yields are good to excellent. The catalyst was easily separated and reused for several runs without appreciable loss of its catalytic activity.
- Rahmani, Salman,Amoozadeh, Ali,Kolvari, Eskandar
-
p. 184 - 188
(2014/11/08)
-
- Reaction of ethyl acetoacetate and 2'-hydroxychalcones: Efficient route to 9-aryl-6H-benzo[c]chromen-6-ones
-
The reaction of ethyl acetoacetate and 2'-hydroxychalcones under atmospheric air to furnish a series of functionalized 6H-benzo[c]chromen-6-ones in moderate yields is reported. The reaction proceeds through trans-esterification, intra-molecular Michael addition, Robinson annulation and oxidative aromatization.
- Masesane, Ishmael B.,Mazimba, Ofentse
-
p. 289 - 294
(2014/06/24)
-
- Synthesis and in-vivo hypolipidemic activity of some novel substituted phenyl isoxazol phenoxy acetic acid derivatives
-
The present study was undertaken to evaluate in-vivo hypolipidemic activity of a novel series of 2-methyl-2-(substituted phenyl isoxazol)phenoxyacetic acid derivatives by triton induced hyperlipidemia in rats. The newly synthesized compounds 5a, 5d and 5g showed significant decrease in the serum TCH, TG, LDL and VLDL along with an increase in serum HDL levels as compared to standard drug Fenofibrate. The treated groups also showed significant decrease in the atherogenic index and increase in % protective activity compared to control group.
- Mokale, Santosh N.,Nevase, Manjusha C.,Sakle, Nikhil S.,Dube, Pritam N.,Shelke, Vishakha R.,Bhavale, Swati A.,Begum, Afreen
-
p. 2155 - 2158
(2014/05/06)
-
- An advanced and novel one-pot synthetic method for diverse benzo[c]chromen-6-ones by transition-metal free mild base-promoted domino reactions of substituted 2-hydroxychalcones with β-ketoesters and its application to polysubstituted terphenyls
-
Novel and efficient one-pot syntheses of a variety of benzo[c]chromen-6-one derivatives were accomplished using Cs2CO3-promoted reactions between substituted 2-hydroxychalcones and β-ketoesters. These reactions involved domino Michael addition/intramolecular aldol/oxidative aromatization/lactonization and provided a rapid synthetic route for the production of biologically interesting novel benzo[c]chromen-6-one molecules bearing several different substituents on benzene rings. As an application of this methodology, several synthesized benzo[c]chromen-6-ones were transformed into highly functionalized novel terphenyls.
- Poudel, Tej Narayan,Lee, Yong Rok
-
p. 919 - 930
(2014/02/14)
-
- Dual inhibition of the α-glucosidase and butyrylcholinesterase studied by Molecular Field Topology Analysis
-
A striking dual inhibition of enzymes α-glucosidase and butyrylcholinesterase by small drug-like molecules, including 1,4-disubstituted-1,2,3-triazoles, chalcones, and benzothiazepines, was rationalized with the help of Molecular Field Topology Analysis, a 3D QSAR technique similar to CoMFA. A common pharmacophore supported the concept of a link existing between type-2 diabetes mellitus and Alzheimer's disease. These findings will be instrumental for rational design of drug candidates for both of these conditions.
- Jabeen, Farukh,Oliferenko, Polina V.,Oliferenko, Alexander A.,Pillai, Girinath G.,Ansari, Farzana Latif,Hall, C. Dennis,Katritzky, Alan R.
-
p. 228 - 242
(2014/05/20)
-
- Effect of phosphorus amount on the particle size and catalytic performance of heterogeneous nickel(ii) schiff-base complex in aldol condensation reaction
-
The organic-inorganic hybrid of citric acid, tetraethoxysilane (TEOS), and triethylphosphate (TEP) doped by a nickel Schiff-base complex was prepared by sol-gel method. The prepared composites were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), transmittance electron microscopy (TEM), scanning tunnelling microscopy (STM), and infrared spectroscopy (IR). In order to determine the phosphorus amount effect on the catalytic activity of the prepared composites, the aldol condensation was used as a model reaction. The results revealed that the composite with 10% phosphorus is a better catalyst in comparison with other composites.
- Eshtiagh-Hosseini, Hossein,Tabari, Taymaz
-
p. 1778 - 1791
(2013/11/06)
-