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https://ir.swu.ac.th/jspui/handle/123456789/13782| Title: | Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors |
| Authors: | Pingaew R. Prachayasittikul V. Mandi P. Nantasenamat C. Prachayasittikul S. Ruchirawat S. Prachayasittikul V. |
| Keywords: | 1,2,3 triazole derivative 1,2,3 triazole sulfonamide derivative 4 [[1 [3 [(3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 4 [[1 [3 [(6,7 dimethoxy 3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [3 [(3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [3 [(6,7 dimethoxy 3,4 dihydroisoquinolin 2 (1h)yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one aromatase inhibitor coumarin oxymethyl functional group ketoconazole letrozole naphthalene oxymethyl phenoxymethyl phenyl group sulfonamide sulfonyl group unclassified drug antineoplastic agent aromatase aromatase inhibitor CYP19A1 protein, human isoquinoline derivative protein binding sulfonamide triazole derivative animal cell Article binding affinity binding site carbon nuclear magnetic resonance chemical interaction chemical reaction Click reaction concentration response controlled study drug cytotoxicity drug mechanism drug potency drug safety drug screening drug synthesis enzyme active site enzyme inhibition hydrogen bond hydrophobicity IC50 mass spectrometry molecular docking nonhuman pi pi stacking interaction proton nuclear magnetic resonance structure activity relation Vero cell line animal cell survival chemical phenomena chemistry Chlorocebus aethiops drug effects human synthesis Animals Antineoplastic Agents Aromatase Aromatase Inhibitors Catalytic Domain Cell Survival Cercopithecus aethiops Humans Hydrogen Bonding Hydrophobic and Hydrophilic Interactions Isoquinolines Molecular Docking Simulation Protein Binding Structure-Activity Relationship Sulfonamides Triazoles Vero Cells |
| Issue Date: | 2015 |
| Abstract: | Abstract A series of 1,4-disubstituted-1,2,3-triazoles (13-35) containing sulfonamide moiety were synthesized and evaluated for their aromatase inhibitory effects. Most triazoles with open-chain sulfonamide showed significant aromatase inhibitory activity (IC50 = 1.3-9.4 μM). Interestingly, the meta analog of triazole-benzene-sulfonamide (34) bearing 6,7-dimethoxy substituents on the isoquinoline ring displayed the most potent aromatase inhibitory activity (IC50 = 0.2 μM) without affecting normal cell. Molecular docking of these triazoles against aromatase revealed that the compounds could snugly occupy the active site of the enzyme through hydrophobic, π-π stacking, and hydrogen bonding interactions. The potent compound 34 was able to form hydrogen bonds with Met374 and Ser478 which were suggested to be the essential residues for the promising inhibition. The study provides compound 34 as a potential lead molecule of anti-aromatase agent for further development. © 2015 Elsevier Ltd. |
| URI: | https://ir.swu.ac.th/jspui/handle/123456789/13782 https://www.scopus.com/inward/record.uri?eid=2-s2.0-84937425435&doi=10.1016%2fj.bmc.2015.04.036&partnerID=40&md5=ded6150540b91998db68cccbfd84b0e8 |
| ISSN: | 9680896 |
| Appears in Collections: | Scopus 1983-2021 |
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