A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles: Synthesis and Anti-Inflammatory Activity

A. V. Lipeeva, M. P. Dolgikh, T. G. Tolstikova, E. E. Shults

Research output: Contribution to journalArticlepeer-review

Abstract

In the reaction of coumarin peuruthenicin with α,ω-dibromoalkanes, the corresponding 7-(ω-bromoalkyloxy)coumarins have been synthesized. The interaction of the resulting compounds with sodium azide has yielded 7-(ω-azidoalkyl)-substituted peuruthenicin derivatives, which exhibited high activity in the Cu(I)-catalyzed Huisgen cycloaddition reaction with the propargyl ester of betulonic acid. As a result of the reaction, 28-O-(chromenoalkyl-triazolylmethyl)lupenones have been synthesized. The reaction of betulonic acid propargyl ester with 2-azidooreoselones in the presence of aqueous copper sulfate and sodium ascorbate has led to the corresponding (furochromen-triazolyl)-20(29)-lupen-3-ones. The newly synthesized hybrid compound triterpenoid furocoumarin containing a triazole linker exhibits anti-inflammatory activity in a model of histamine inflammation.

Original languageEnglish
Pages (from-to)125-132
Number of pages8
JournalRussian Journal of Bioorganic Chemistry
Volume46
Issue number2
DOIs
Publication statusPublished - 1 Mar 2020

Keywords

  • 1,3-dipolar cycloaddition
  • azides
  • betulin
  • coumarins
  • furocoumarins
  • triterpenoids
  • 3-dipolar cycloaddition
  • MOLECULAR DOCKING
  • 1
  • BETULINIC ACID
  • BETULONIC ACID-AMIDES
  • DERIVATIVES
  • TRANSFORMATIONS

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