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

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-4 H-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. ED 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. [ABSTRACT FROM AUTHOR]