Highly potent analgesic activity of monoterpene-derived (2S,4aR,8R,8aR)-2-aryl-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols

Highly potent analgesic activity of monoterpene-derived (2S,4aR,8R,8aR)-2-aryl-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: 2014, Volume: 23, Number: 12, Pages: 5063-5073 Pages count : DOI: 10.1007/s00044-014-1071-4

Tags

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

Authors

Il'ina Irina ¹ , Mikhalchenko Oksana ¹ , Pavlova Alla ¹ , Korchagina Dina ¹ , Tolstikova Tat'yana ¹ , Volcho Konstantin ¹ , Salakhutdinov Nariman ^1,2 , Pokushalov Evgeniy ³

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
3	(Данные Web of science) State Res Inst Circulat Pathol, Novosibirsk 630055, Russia

New chiral heterocyclic compounds with a hexahydro-2H-chromene framework were synthesized by reactions of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes in the presence of montmorillonite clay. The analgesic activity of the compounds was studied in vivo. The majority of these compounds showed significant analgesic activity in the acetic acid-induced writhing test; the compounds containing one hydroxy and one methoxy substituents also showed analgesic activity in the hot-plate test. (2S,4aR,8R,8aR)-2-(3-Hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol was as effective as the diclofenac sodium reference taken in the same dose in both tests. It has low acute toxicity and is very promising for further development.

Il'ina I. , Mikhalchenko O. , Pavlova A. , Korchagina D. , Tolstikova T. , Volcho K. , Salakhutdinov N. , Pokushalov E.
Highly potent analgesic activity of monoterpene-derived (2S,4aR,8R,8aR)-2-aryl-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols
Medicinal Chemistry Research. 2014. V.23. N12. P.5063-5073. DOI: 10.1007/s00044-014-1071-4 WOS Scopus РИНЦ OpenAlex

Published online:	Jun 26, 2014
Published print:	Dec 1, 2014

Web of science:	WOS:000344165100006
Scopus:	2-s2.0-84911499505
Elibrary:	24944206
OpenAlex:	W2027380442

DB	Citing
Web of science	24
Scopus	24
Elibrary	27
OpenAlex	24