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

— 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...

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Veröffentlicht in:Russian journal of bioorganic chemistry 2020-03, Vol.46 (2), p.125-132
Hauptverfasser: Lipeeva, A. V., Dolgikh, M. P., Tolstikova, T. G., Shults, E. E.
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Sprache:eng
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Zusammenfassung:— 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.
ISSN:1068-1620
1608-330X
DOI:10.1134/S1068162020010161