Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol

Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol Full article

Journal

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

Output data

Year: 2016, Volume: 25, Number: 7, Pages: 1369-1383 Pages count : 15 DOI: 10.1007/s00044-016-1573-3

Tags

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

Authors

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

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Novosibirsk Organ Chem Inst, Lavrentjev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia

A large set of chiral heterocyclic compounds with the octahydro-2H-chromene scaffold was first obtained by a reaction of (-)-isopulegol and (+)-neoisopulegol with furan-2-carbaldehyde, thiophene-2-carbaldehyde and their derivatives and isomers in the presence of montmorillonite K10 clay. Most of the (-)-isopulegol-derived compounds exhibited a significant analgesic activity in the acetic acid-induced writhing test. Compound 3b obtained by a reaction of (-)-isopulegol with thiophene-2-carbaldehyde demonstrated a significant analgesic effect in this test within 15 min after oral administration at the dose of 1 mg/kg and retains the effect for at least 24 h. Compound 3b exhibited analgesic activity in the hot plate test also. A change in the sulfur atom position in the aromatic ring was found to lead to the effect reversal in the hot plate test.

Nazimova E. , Pavlova A. , Mikhalchenko O. , Il'ina I. , Korchagina D. , Tolstikova T. , Volcho K. , Salakhutdinov N.
Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol
Medicinal Chemistry Research. 2016. V.25. N7. P.1369-1383. DOI: 10.1007/s00044-016-1573-3 WOS Scopus РИНЦ

Published online:	Apr 18, 2016
Published print:	Jul 1, 2016

Web of science	WOS:000378573400008
Scopus	2-s2.0-84964380873
Elibrary	27040620
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