

SYNTHESIS, CYTOTOXICITY, AND α-GLUCOSIDASE INHIBITORY ACTIVITY OF TRITERPENIC AND SITOSTEROL TETRAZOLE DERIVATIVES

Abstract
A series of new triterpenic and sitosterol derivatives containing 1,2,3,4-(tetrazol-5-yl)ethoxy and -ethoxyimine fragments at positions C-2, C-3, and C-12 have been synthesized by 1,3-dipolar cycloaddition of nitriles to sodium azide. The structure of the obtained compounds was confirmed by NMR spectroscopy, including two-dimensional correlation experiments, and mass spectrometry. It was found that such steric factors as the presence of 23,24-gem-dimethyl groups or a second cyanoethyl group at position C-2 affect the yield of the reaction product. In vitro studies have shown that methyl 2-[2-(1Н-tetrazol-5-yl)]-2,4-seco-3-norlupa-4(23),20(29)-dien-28-oate and 24-ethyl-3-[2-(1Н-tetrazol-5-yl)ethoxy]cholestan-5-ene have the highest anticancer and α-glucosidase inhibitory activities, respectively.
Keywords
lupane; oleanane; β-sitosterol; tetrazoles; triterpenoids; ursane, cytotoxicity; 1,3-dipolar cycloaddition; α-glucosidase inhibitor.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv