A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles: Synthesis and Anti-Inflammatory Activity
| Autor: | T. G. Tolstikova, Elvira E. Shults, A. V. Lipeeva, M. P. Dolgikh |
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| Rok vydání: | 2020 |
| Předmět: |
0301 basic medicine
Sodium ascorbate 010405 organic chemistry Chemistry Furocoumarin Organic Chemistry Triazole Coumarin 01 natural sciences Biochemistry Medicinal chemistry Cycloaddition 0104 chemical sciences 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology Propargyl Sodium azide Linker |
| Zdroj: | Russian Journal of Bioorganic Chemistry. 46:125-132 |
| ISSN: | 1608-330X 1068-1620 |
| DOI: | 10.1134/s1068162020010161 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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