New 30-substituted derivatives of pentacyclic triterpenes: preparation, biological activity, and molecular docking study

A series of 30-substituted derivatives of 3,28-O,O'-diacetylbetulin 4-19 were prepared and assessed for anticancer activities in vitro against five human cancer cell lines (SNB-19, C-32, SKOV-3, MCF-7, and T47D). The triterpene 14, containing the butyryloxycarbonyl group at the C-30 position, showed the highest cytotoxicity, with IC50 values within the range of 1.24 to 6.03 mu M towards applied cancer cells. The ADME study of the betulinines 4-19 were performed by determination of molecular weight (M), hydrogen bond acceptors (nHBA), hydrogen bond donors (nHBD), lipophilicity (cLogP), rotatable bonds (nROTB) and topological polar surface area (TPSA). Molecular docking was applied to examine the probable interaction between the new synthesized compounds and the Aktl kinase. The analysis showed that triterpenes 13-16 formed numerous hydrophobic interactions inside the binding pocket of Akt1. (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

A series of betulin derivatives were synthesized and evaluated for anticancer activity, with one compound showing high cytotoxicity. Molecular docking and ADME studies were also conducted for further analysis.