A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles

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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. / Lipeeva, A. V.; Dolgikh, M. P.; Tolstikova, T. G. et al.

In: Russian Journal of Bioorganic Chemistry, Vol. 46, No. 2, 01.03.2020, p. 125-132.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{5edcade5e6e04aa4aa4c72065d955faf,

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

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.",

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

author = "Lipeeva, {A. V.} and Dolgikh, {M. P.} and Tolstikova, {T. G.} and Shults, {E. E.}",

year = "2020",

month = mar,

day = "1",

doi = "10.1134/S1068162020010161",

language = "English",

volume = "46",

pages = "125--132",

journal = "Russian Journal of Bioorganic Chemistry",

issn = "1068-1620",

publisher = "MAIK NAUKA/INTERPERIODICA/SPRINGER",

number = "2",

}

RIS

TY - JOUR

T1 - A Study of Plant Coumarins. 18. Conjugates of Coumarins with Lupane Triterpenoids and 1,2,3-Triazoles

T2 - Synthesis and Anti-Inflammatory Activity

AU - Lipeeva, A. V.

AU - Dolgikh, M. P.

AU - Tolstikova, T. G.

AU - Shults, E. E.

PY - 2020/3/1

Y1 - 2020/3/1

N2 - 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.

AB - 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.

KW - 1,3-dipolar cycloaddition

KW - azides

KW - betulin

KW - coumarins

KW - furocoumarins

KW - triterpenoids

KW - 3-dipolar cycloaddition

KW - MOLECULAR DOCKING

KW - 1

KW - BETULINIC ACID

KW - BETULONIC ACID-AMIDES

KW - DERIVATIVES

KW - TRANSFORMATIONS

UR - http://www.scopus.com/inward/record.url?scp=85083962799&partnerID=8YFLogxK

U2 - 10.1134/S1068162020010161

DO - 10.1134/S1068162020010161

M3 - Article

AN - SCOPUS:85083962799

VL - 46

SP - 125

EP - 132

JO - Russian Journal of Bioorganic Chemistry

JF - Russian Journal of Bioorganic Chemistry

SN - 1068-1620

IS - 2

ER -

ID: 24231014

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

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