Publication: Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors
Issued Date
2015-01-01
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ISSN
14643391
09680896
09680896
Other identifier(s)
2-s2.0-84937425435
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Mahidol University
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SCOPUS
Bibliographic Citation
Bioorganic and Medicinal Chemistry. Vol.23, No.13 (2015), 3472-3480
Suggested Citation
Ratchanok Pingaew, Veda Prachayasittikul, Prasit Mandi, Chanin Nantasenamat, Supaluk Prachayasittikul, Somsak Ruchirawat, Virapong Prachayasittikul Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors. Bioorganic and Medicinal Chemistry. Vol.23, No.13 (2015), 3472-3480. doi:10.1016/j.bmc.2015.04.036 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/35617
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Title
Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors
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Abstract
© 2015 Elsevier Ltd. 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.