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Synthesis, Cytotoxicity, and [alpha]-glucosidase Inhibitory Activity of Triterpenic and Sitosterol Tetrazole Derivatives

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

Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2021-09, Vol.57 (9), p.920 [Periódico revisado por pares]

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Título:
Synthesis, Cytotoxicity, and [alpha]-glucosidase Inhibitory Activity of Triterpenic and Sitosterol Tetrazole Derivatives
Autor: Petrova, Anastasiya V ; Poptsov, Alexander I ; Thu, Ha Nguyen Thi ; Van Tuyen, Nguyen ; Khusnutdinova, Elmira F ; Babkov, Denis A ; Kazakova, Oxana B
Assuntos: Nitriles ; Nuclear magnetic resonance spectroscopy ; Sterols
É parte de: Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2021-09, Vol.57 (9), p.920
Descrição: 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-(1Ð-tetrazol-5-yl)]-2,4-seco-3-norlupa-4(23),20(29)-dien-28-oate and 24-ethyl-3-[2-(1Ð-tetrazol-5-yl)ethoxy]cholestan-5-ene have the highest anticancer and [alpha]-glucosidase inhibitory activities, respectively.
Editor: Springer
Idioma: Inglês

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