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Synthesis and Analgesic Activity Assessment of Furanolabdanoid Conjugates with Glucuronic Acid Научная публикация

Журнал Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388
Вых. Данные Год: 2020, Том: 56, Номер: 4, Страницы: 678-687 Страниц : 10 DOI: 10.1007/s10600-020-03119-7
Ключевые слова diterpenoids; glucuronic acid; glycoconjugate; azides; CuAAC reaction; analgesic activity
Авторы Brusentseva O.I. 1 , Kharitonov Yu.V. 1 , Dolgikh M.P. 1 , Tolstikova T.G. 1 , Shul'ts E.E. 1
Организации
1 (Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Prosp Lavrenteva, Novosibirsk 630090, Russia

Реферат: Phlomisoic acid reacted with methyl-1-deoxy-2,3,4-tri-O-acetyl-1-bromo-alpha-D-glucopyranuronate to form the 18-O-beta-D-(glucuronopyranoside)-6 '-O-methyl ester of 15,16-epoxylabda-8(9),13,14-triene. Reductive amination of methyl 16-formyl-15,16-epoxylabda-8(9),13,14-trienoate or this beta-D-glucuronopyranoside of 16-formyl-15,16-epoxylabda-8(9),13,14-triene by propargylamine in the presence of NaBH(4)gave the corresponding 16-propargylaminomethyl-15,16-epoxylabda-8(9),13,14-trienes. Copper-catalyzed azide-alkyne cycloaddition of the new terpenoid alkynes and the propargylamide of phlomisoic acid with methyl 1-deoxy-2,3,4-tri-O-acetyl-1-azido-alpha-D-glucopyranuronate synthesized the corresponding labdanoid glucuronides and diglucuronide. Selective screening of the labdanoid triazolylglucuronides identified compounds with analgesic activity in chemical and thermal irritation tests.
Библиографическая ссылка: Brusentseva O.I. , Kharitonov Y.V. , Dolgikh M.P. , Tolstikova T.G. , Shul'ts E.E.
Synthesis and Analgesic Activity Assessment of Furanolabdanoid Conjugates with Glucuronic Acid
Chemistry of Natural Compounds. 2020. V.56. N4. P.678-687. DOI: 10.1007/s10600-020-03119-7 WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована в печати: 1 июл. 2020 г.
Опубликована online: 26 июл. 2020 г.
Идентификаторы БД:
Web of science: WOS:000552249600010
Scopus: 2-s2.0-85088596655
РИНЦ: 45419368
OpenAlex: W3044465953
Цитирование в БД:
БД Цитирований
Web of science 3
Scopus 3
РИНЦ 2
OpenAlex 3
Альметрики: