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

Anastasiya V. Petrova, Alexander I. Poptsov, Ha Thi Thu Nguyen, Tuyen Van Nguyen, Elmira F. Khusnutdinova, Denis A. Babkov, Oxana B. Kazakova
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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.

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