Synthesis and evaluation of 2,3-indolotriterpenoids as new α-glucosidase inhibitors

A series of ring-A fused heterocycles of lupane, oleanane, ursane and dammarane triterpenoids were synthesized and evaluated for their inhibitory activity against α-glucosidase. An influence of the different types of triterpenoids with indole and pyrazine cycles on the activity was revealed. Among t...

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Bibliographic Details
Published in:Medicinal chemistry research 2017-11, Vol.26 (11), p.2737-2742
Main Authors: Khusnutdinova, Elmira F., Smirnova, Irina E., Kazakova, Oxana B., Petrova, Anastasiya V., Ha, Nguyen Thi Thu, Viet, Do Quoc
Format: Article
Language:English
Subjects:
Acarbose
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Glucosidase
Indoles
Original Research
Pharmacology/Toxicology
Pyrazine
Triterpenoids
α-Glucosidase
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Summary:A series of ring-A fused heterocycles of lupane, oleanane, ursane and dammarane triterpenoids were synthesized and evaluated for their inhibitory activity against α-glucosidase. An influence of the different types of triterpenoids with indole and pyrazine cycles on the activity was revealed. Among them, 2,3-indolo-lup-20(29)-en-28-oic acid with an IC 50 of 1.8 µM was the most active compound being 221-fold more active than the market drug acarbose. In the most cases, the replacement of the indole by the pyrazine fragment provided the decreasing of activity (except dammarane type pyrazine derivative). Graphical Abstract
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-017-1972-0