Publication: Synthesis, molecular docking, and QSAR study of bis-sulfonamide derivatives as potential aromatase inhibitors
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Issued Date
2019-10-01
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ISSN
14643391
09680896
09680896
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2-s2.0-85070395327
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Mahidol University
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SCOPUS
Bibliographic Citation
Bioorganic and Medicinal Chemistry. Vol.27, No.19 (2019)
Suggested Citation
Ronnakorn Leechaisit, Ratchanok Pingaew, Veda Prachayasittikul, Apilak Worachartcheewan, Supaluk Prachayasittikul, Somsak Ruchirawat, Virapong Prachayasittikul Synthesis, molecular docking, and QSAR study of bis-sulfonamide derivatives as potential aromatase inhibitors. Bioorganic and Medicinal Chemistry. Vol.27, No.19 (2019). doi:10.1016/j.bmc.2019.08.001 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/50066
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Title
Synthesis, molecular docking, and QSAR study of bis-sulfonamide derivatives as potential aromatase inhibitors
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Abstract
© 2019 Elsevier Ltd A library of bis-sulfonamides (9–26) were synthesized and tested for their aromatase inhibitory activities. Interestingly, all bis-sulfonamide derivatives inhibited the aromatase with IC50 range of 0.05–11.6 μM except for compound 23. The analogs 15 and 16 bearing hydrophobic chloro and bromo groups exhibited the potent aromatase inhibitory activity in sub-micromolar IC50 values (i.e., 50 and 60 nM, respectively) with high safety index. Molecular docking revealed that the chloro and bromo benzenesulfonamides (15 and 16) may play role in the hydrophobic interaction with Leu477 of the aromatase to mimic steroidal backbone of the natural substrate, androstenedione. QSAR study also revealed that the most potent activity of compounds was governed by van der Waals volume (GATS6v) and mass (Mor03m) descriptors. Finally, the two compounds (15 and 16) were highlighted as promising compounds to be further developed as novel aromatase inhibitors.