Synthesis of Betulonic and Betulinic Acids Derivatives with Sulfonamide Fragment Linked to the Triterpene Core by Amidoalkane Spaser

N. G. Komissarova; Комиссарова Н. Г.; A. V. Orlov; Орлов А. В.; L. V. Spirikhin; Спирихин Л. В.

doi:10.31857/S0044460X24060063

Synthesis of Betulonic and Betulinic Acids Derivatives with Sulfonamide Fragment Linked to the Triterpene Core by Amidoalkane Spaser

Authors: Komissarova N.G.¹, Orlov A.V.¹, Spirikhin L.V.¹
Affiliations:
1. Ufa Federal Research Centre of the Russian Academy of Sciences
Issue: Vol 94, No 6 (2024)
Pages: 722-733
Section: Articles
URL: https://kazanmedjournal.ru/0044-460X/article/view/667390
DOI: https://doi.org/10.31857/S0044460X24060063
EDN: https://elibrary.ru/EZEDBB
ID: 667390

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Abstract

A series of potentially biologically active sulfonamides of betulonic and betulinic acids with a sulfonamide fragment containing residues of dibutylamine or N-heterocycles, which is linked to a triterpene core by an amidoethane or amidopropane spacer, was synthesized. Betulonic acid sulfonamides were obtained by chlorohydride conjugation of acid with 2-aminoethane and 3-aminopropanesulfonamides and used as precursor compounds for the transition to similar betulinic acid derivatives by selective reduction of the 3-keto group with the action of NaBH₄ in EtOH. The structure of all synthesized triterpene sulfonamides was confirmed by 1D and 2D NMR spectroscopy and mass spectrometry.

Keywords

betulonic acid, betulinic acid, amidoalkanesulfonamides

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