Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazopyrimidine derivatives

Article abstract of DOI:10.1016/0223-5234(94)90097-3

The synthesis of a group of imidazo<1,2-a>pyrimidine-2-carboxylic esters, acids and amides is described.The structures of the new compounds are supported by 1H- and 13C-NMR spectra.These compounds were tested in vivo for their antiinflammatory and analgesic activities as well as for their ulcerogenic action.The ester 5b, the acid 6c and the amide 7a showed antiinflammatory action in the rat paw edema (ca. 1/3 x indomethacin), while almost all compounds displayed significant analgesic activity in the acetic acid writhing test, particularly the 5-chloro-7-methyl derivatives 5a, 6a and 7a (ca 1/5 x indomethacin).All new compounds were found to be lacking in inhibitory activity on cyclooxygenase in vitro. imidazo<1,2-a>pyrimidines / antiinflammatory activity / analgesic activity / ulcerogenic activity / cyclooxygenase inhibition