A variety of new and earlier synthesized lupane, oleanane, ursane and dammarane triterpenoids have been investigated for their inhibitory activity against α-glucosidase. 2,3-Indole-21β-acetyl-20β,28-epoxy-18α,19βH-ursane and 3-oxo-3A-homo-3a-aza-20(S)-hydroxydammar-24(25)-ene were synthesized for the first time. The compounds 3, 4, 8–11 and 14 demonstrated strong in vitro inhibitory activity towards α-glucosidase with IC50 values of 37.5–115.1 μM. 3-Deoxy-3a-homo-3a-aza-28-cinnamoyloxy-20(29)-lupene, with an IC50 of 6.67 μM was 60-fold more active than the market drug acarbose.
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