Synthesis and analgesic activity of monoterpenoid-derived 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ols

Synthesis and analgesic activity of monoterpenoid-derived 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ols Full article

Journal

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

Output data

Year: 2014, Volume: 23, Number: 4, Pages: 1709-1717 Pages count : DOI: 10.1007/s00044-013-0772-4

Tags

Terpenoid; Heterocyclic compounds; Benzodioxine; Analgesic activity; Acetic acid-induced writhing test; Hot-plate test

Authors

Kurbakova Svetlana ¹ , Il'ina Irina ¹ , Pavlova Alla ¹ , Korchagina Dina ¹ , Yarovaya Olga ¹ , Tolstikova Tat'yana ¹ , Volcho Konstantin ¹ , Salakhutdinov Nariman ¹

Affiliations

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

A new series of chiral heterocyclic compounds with frameworks of different types were synthesized by reactions of verbenol epoxide with aromatic aldehydes in the presence of montmorillonite clay. The analgesic activity of compounds with frameworks of 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol type was studied in vivo. The majority of these compounds showed a significant analgesic activity in the acetic acid-induced writhing test; two compounds also showed analgesic activity in the hot-plate test. ED50 in acetic acid-induced writhing test for compound where aryl is 4-chlorophenyl substituent was determined to be 4.5 mg/kg. Compound with 4-nitrophenyl substituent demonstrated high analgesic activity in both tests.

Kurbakova S. , Il'ina I. , Pavlova A. , Korchagina D. , Yarovaya O. , Tolstikova T. , Volcho K. , Salakhutdinov N.
Synthesis and analgesic activity of monoterpenoid-derived 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ols
Medicinal Chemistry Research. 2014. V.23. N4. P.1709-1717. DOI: 10.1007/s00044-013-0772-4 WOS Scopus РИНЦ

Published online:	Sep 12, 2013
Published print:	Apr 1, 2014

Web of science	WOS:000331003400010
Scopus	2-s2.0-84899408591
Elibrary	24047209
OpenAlex	W1989053497