A set of new heterocyclic compounds with different types of framework, including a new type of framework, were synthesized by reactions of verbenol epoxide and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes containing three methoxy groups. The analgesic activity of these substances was studied. Three compounds possessed considerable activity in vivo in the acetic acid-induced writhing test. (2S,4R,4aR,8S,8aR)-4,7-Dimethyl-2-(2,4,5-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-4,8-epoxychromene exhibited high analgesic activity in both acetic acid-induced writhing and hot plate tests; its selectivity index IS50 exceeded 60.
Verbenol epoxide Terpenoid Heterocyclic compounds Analgesic activity Acetic acid-induced writhing test Hot plate test
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Authors are grateful to the Presidium of Russian Academy of Sciences (Program No. 28) and Russian Foundation for Basic Research (Grant No. 10-03-00230a) for the financial support.
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