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A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles: Synthesis and Anti-Inflammatory Activity
Russian Journal of Bioorganic Chemistry ( IF 1.1 ) Pub Date : 2020-03-01 , DOI: 10.1134/s1068162020010161
A. V. Lipeeva , M. P. Dolgikh , T. G. Tolstikova , E. E. Shults

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.

中文翻译:

植物香豆素的研究。18. 香豆素与羽扇豆三萜和 1,2,3-三唑的结合物:合成和抗炎活性

摘要 — 香豆素 peuruthenicin 与 α,ω-二溴烷烃反应合成了相应的 7-(ω-溴烷氧基)香豆素。所得化合物与叠氮化钠的相互作用产生了 7-(ω-叠氮烷基)-取代的 peuruthenicin 衍生物,其在 Cu(I) 催化的 Huisgen 环加成反应中与桦木酸炔丙酯反应中表现出高活性。作为反应的结果,已经合成了 28-O-(色烯烷基-三唑基甲基)lupenones。在硫酸铜水溶液和抗坏血酸钠存在下,桦木酸炔丙酯与 2-叠氮酮烯酮的反应产生了相应的 (呋喃苯甲酸三唑基)-20(29)-lupen-3-ones。
更新日期:2020-03-01
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