A series of lupeol derivatives 2, 2a-2f, 2a-2h, 3a-3e, and 4a-4b were designed, synthesized and evaluated for their α-glucosidase inhibitory and cytotoxic activities. Among synthetic derivatives, lupeol analogues 2b and 2e containing a benzylidene chain exhibited the best activity against α-glucosidase and superior to the positive agent with the IC 50 values of 29.4 ± 1.33 and 20.1 ± 0.91 μM, respectively. Lupeol analogues 2d and 3a showed weak cytotoxicity against K562 cell line with the IC 50 values of 76.6 ± 2.40 and 94.4 ± 1.51 μM, respectively.
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