Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols

Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols Full article

Journal

Medicinal Chemistry Research
ISSN: 1054-2523 , E-ISSN: 1554-8120

Output data

Year: 2015, Volume: 24, Number: 11, Pages: 3821-3830 Pages count : DOI: 10.1007/s00044-015-1426-5

Tags

Terpene; Chromene; Heterocyclic compounds; Analgesic activity; Acetic acid-induced writhing test; Hot plate test; Stereoisomers

Authors

Pavlova Alla ¹ , Mikhalchenko Oksana ¹ , Rogachev Artem ^1,2 , Il'ina Irina ^1,2 , Korchagina Dina ¹ , Gatilov Yuriy ^1,2 , Tolstikova Tat'yana ¹ , Volcho Konstantin ^1,2 , Salakhutdinov Nariman ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Organ Chem Inst, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

2-(3(4)-Hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols were found recently to possess high analgesic activity and low acute toxicity. Stereoisomers of these compounds with high optical purity were synthesized from (+)- and (-)-alpha-pinenes for the first time in this work. The structure of (4S)-4b isomer was confirmed by the XRD data. Studies of analgesic activity of the resulting products demonstrated that neither the absolute configuration nor cis- or trans-arrangement of vicinal oxygen atoms plays a significant role in manifestation of analgesic effect by these isomers, while only (4S)-4b isomer, but not (4R)-4b demonstrated the analgesic effect.

Pavlova A. , Mikhalchenko O. , Rogachev A. , Il'ina I. , Korchagina D. , Gatilov Y. , Tolstikova T. , Volcho K. , Salakhutdinov N.
Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols
Medicinal Chemistry Research. 2015. V.24. N11. P.3821-3830. DOI: 10.1007/s00044-015-1426-5 WOS Scopus РИНЦ

Published online:	Aug 15, 2015
Published print:	Nov 1, 2015

Web of science	WOS:000361758000006
Scopus	2-s2.0-84942503083
Elibrary	24952964
OpenAlex	W2098126832