A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles: Synthesis and Anti-Inflammatory Activity Full article
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Russian Journal of Bioorganic Chemistry
ISSN: 1068-1620 |
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| Output data | Year: 2020, Volume: 46, Number: 2, Pages: 125-132 Pages count : 8 DOI: 10.1134/S1068162020010161 | ||||
| Tags | triterpenoids; betulin; coumarins; furocoumarins; azides; 1; 3-dipolar cycloaddition | ||||
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Abstract:
In the reaction of coumarin peuruthenicin with alpha,omega-dibromoalkanes, the corresponding 7-(omega-bromoalkyloxy)coumarins have been synthesized. The interaction of the resulting compounds with sodium azide has yielded 7-(omega-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.
Cite:
Lipeeva A.V.
, Dolgikh M.P.
, Tolstikova T.G.
, Shults E.E.
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. 2020. V.46. N2. P.125-132. DOI: 10.1134/S1068162020010161 WOS Scopus РИНЦ
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. 2020. V.46. N2. P.125-132. DOI: 10.1134/S1068162020010161 WOS Scopus РИНЦ
ArticleLinkType.TRANSLATED_TO_ORIGINAL:
Липеева А.В.
, Долгих М.П.
, Толстикова Т.Г.
, Шульц Е.Е.
ИССЛЕДОВАНИЕ РАСТИТЕЛЬНЫХ КУМАРИНОВ. 18. КОНЪЮГАТЫ КУМАРИНОВ С ЛУПАНОВЫМИ ТРИТЕРПЕНОИДАМИ И 1,2,3-ТРИАЗОЛАМИ: СИНТЕЗ И ПРОТИВОВОСПАЛИТЕЛЬНАЯ АКТИВНОСТЬ
Биоорганическая химия (RUSS J BIOORG CHEM+). 2020. Т.46. №2. С.115-123. DOI: 10.31857/S0132342320010194 РИНЦ
ИССЛЕДОВАНИЕ РАСТИТЕЛЬНЫХ КУМАРИНОВ. 18. КОНЪЮГАТЫ КУМАРИНОВ С ЛУПАНОВЫМИ ТРИТЕРПЕНОИДАМИ И 1,2,3-ТРИАЗОЛАМИ: СИНТЕЗ И ПРОТИВОВОСПАЛИТЕЛЬНАЯ АКТИВНОСТЬ
Биоорганическая химия (RUSS J BIOORG CHEM+). 2020. Т.46. №2. С.115-123. DOI: 10.31857/S0132342320010194 РИНЦ
Dates:
| Published print: | Mar 1, 2020 |
| Published online: | Apr 27, 2020 |
Identifiers:
| Web of science | WOS:000529094300001 |
| Scopus | 2-s2.0-85083962799 |
| Elibrary | 43286844 |
| OpenAlex | W3019422202 |