Medicinal Chemistry Research | 2019
Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones
Abstract
A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five compounds exhibited activity against G. lamblia at IC 50 ’s\u2009<5\u2009μM. The chalcone 3m exhibited the highest antigiardial activity (IC 50 \u2009=\u20091.03\u2009μM), even more than the positive control (metronidazole, IC 50 \u2009=\u20091.4\u2009μM), and selectivity (SI\u2009=\u200938.9). A preliminary SAR study suggested that electrophylicity has not relationship with antigiardiasic activity, and the docking study reveals that synthesized chalcones bind at zone 3 of colchicine site, therefore presumably the action mechanism of the synthesized chalcones does not follow the Michael acceptor mechanism.