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https://ir.swu.ac.th/jspui/handle/123456789/13800| Title: | Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents |
| Authors: | Pingaew R. Saekee A. Mandi P. Nantasenamat C. Prachayasittikul S. Ruchirawat S. Prachayasittikul V. |
| Keywords: | 4 ((1 (3 (3 (2,3 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 4 ((1 (3 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 4 ((1 (3 (3 (3,4 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 4 ((1 (4 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 4 ((1 (4 (3 (3,4,5 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yll)methoxy) 2h chromen 2 one 7 ((1 (3 (3 (2,3 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 7 ((1 (3 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 7 ((1 (3 (3 (3,4 dimethoxyphenyl)acryloyl)phenyl) 1 h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 7 ((1 (4 (3 (2,3 dimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 7 ((1 (4 (3 (2,3,4 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one 7 ((1 (4 (3 (3,4,5 trimethoxyphenyl)acryloyl)phenyl) 1h 1,2,3 triazol 4 yl)methoxy) 2h chromen 2 one alpha tubulin antimalarial agent antineoplastic agent beta tubulin chalcone derivative coumarin derivative etoposide falcipain 2 unclassified drug 1,2,3 triazole derivative 4 [[1 [3 [3 (2,3 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 4 [[1 [3 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 4 [[1 [3 [3 (3,4 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 4 [[1 [4 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 4 [[1 [4 [3 (3,4,5 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [3 [3 (2,3 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [3 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [3 [3 (3,4 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [4 [3 (2,3 dimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [4 [3 (2,3,4 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one 7 [[1 [4 [3 (3,4,5 trimethoxyphenyl)acryloyl]phenyl] 1h 1,2,3 triazol 4 yl]methoxy] 2h chromen 2 one antimalarial agent antineoplastic agent chalcone derivative colchicine coumarin derivative dihydroartemisinin doxorubicin ellipticine etoposide falcipain 2 n [n (3 carboxyoxirane 2 carbonyl)leucyl]agmatine tubulin antimalarial agent antineoplastic agent chalcone coumarin coumarin derivative cysteine proteinase triazole derivative antimalarial activity antineoplastic activity article cancer cell line carbon nuclear magnetic resonance cycloaddition cytotoxicity drug structure drug synthesis HepG2 cell line human human cell molecular docking Plasmodium falciparum proton nuclear magnetic resonance A549 cell line AGMK cell line animal cell antimalarial activity Article cholangiocarcinoma cell line controlled study crystal structure drug binding site drug cytotoxicity drug potency drug screening drug synthesis hydrogen bond IC50 leukemia cell line lymphatic leukemia molecular docking nonhuman structure activity relation Vero cell line chemistry drug effects metabolism protein conformation synthesis tumor cell line Antimalarials Antineoplastic Agents Cell Line, Tumor Chalcone Chemistry Techniques, Synthetic Coumarins Cysteine Endopeptidases Humans Molecular Docking Simulation Plasmodium falciparum Protein Conformation Triazoles Tubulin |
| Issue Date: | 2014 |
| Abstract: | A new series of chalcone-coumarin derivatives (9-19) linked by the 1,2,3-triazole ring were synthesized through the azide/alkyne dipolar cycloaddition. Hybrid molecules were evaluated for their cytotoxic activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) and antimalarial activity toward Plasmodium falciparum. Most of the synthesized hybrids, except for analogs 10 and 16, displayed cytotoxicity against MOLT-3 cell line without affecting normal cells. Analogs (10, 11, 16 and 18) exhibited higher inhibitory efficacy than the control drug, etoposide, in HepG2 cells. Significantly, the high cytotoxic potency of the hybrid 11 was shown to be non-toxic to normal cells. Interestingly, the chalcone-coumarin 18 was the most potent antimalarial compound affording IC50 value of 1.60 μM. Molecular docking suggested that the cytotoxicity of reported hybrids could be possibly due to their dual inhibition of α- and β-tubulins at GTP and colchicine binding sites, respectively. Furthermore, falcipain-2 was identified to be a plausible target site of the hybrids given their antimalarial potency. © 2014 Elsevier Masson SAS. All rights reserved. |
| URI: | https://ir.swu.ac.th/jspui/handle/123456789/13800 https://www.scopus.com/inward/record.uri?eid=2-s2.0-84905161366&doi=10.1016%2fj.ejmech.2014.07.087&partnerID=40&md5=4c490e6ea3dea932430f55e04459096e |
| ISSN: | 2235234 |
| Appears in Collections: | Scopus 1983-2021 |
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