Abstract: 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.

Cite: 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

Dates:

Published print:	Jul 1, 2020
Published online:	Jul 26, 2020

Identifiers:

Web of science	WOS:000552249600010
Scopus	2-s2.0-85088596655
Elibrary	45419368
OpenAlex	W3044465953

Altmetrics: