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

Authors

  • Anastasiya V. Petrova Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Science, 71 Octyabrya Ave., Ufa 450054, Russia
  • Alexander I. Poptsov Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Science, 71 Octyabrya Ave., Ufa 450054, Russia
  • Ha Thi Thu Nguyen Institute of Chemistry, Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay Dist., Hanoi, Vietnam
  • Tuyen Van Nguyen Institute of Chemistry, Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay Dist., Hanoi, Vietnam
  • Elmira F. Khusnutdinova Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Science, 71 Octyabrya Ave., Ufa 450054, Russia
  • Denis A. Babkov Scientific Center for Innovative Drugs, Volgograd State Medical University, 39 Novorossiyskaya St., Volgograd 400087, Russia
  • Oxana B. Kazakova Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Science, 71 Octyabrya Ave., Ufa 450054, Russia

DOI:

https://doi.org/10.1007/6265

Keywords:

lupane, oleanane, β-sitosterol, tetrazoles, triterpenoids, ursane, cytotoxicity, 1, 3-dipolar cycloaddition, α-glucosidase inhibitor.

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.

Author Biography

Anastasiya V. Petrova, Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Science, 71 Octyabrya Ave., Ufa 450054, Russia

junior researcher of laboratory of organic functional materials

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Published

2021-09-22

Issue

Vol. 57 No. 9 (2021)

Section

Original Papers