Synthesis and Immunological Activity of 5,6,6a,8,9,11a-Hexahydronaphthimidazothiazoles and 5,6,6a,9,10,11a-Hexahydronaphthimidazothiazoles

Article abstract of DOI:10.1021/jm00186a015

A series of 5,6,6a,8,9,11a-hexahydronaphth<1',2':4,5>imidazo<2,1-b>thiazoles (17 and 20) and 5,6,6a,9,10,11a-hexahydronaphth<2',1':4,5>imidazo<2,1-b>thiazoles (18) has been synthesized with cis- and/or trans-1,2-diamino-1,2,3,4-tetrahydronaphthalenes (12) as the key intermediates and subsequently evaluated for immunological activity (effects on antibody formation and delayed-type hypersensitivity reaction).Among the compounds tested, trans-5,6,6a,8,9,11a-hexahydronaphth<1',2':4,5>imidazo(2,1-b>thiazole (trans-17a) and (+/-)-5,6,6aβ-8,9,11aα-hexahydro-8β-hydroxy-9β-methyl-8α-phenylnaphth<1',2':4,5>imidazo<2,1-b>thiazole (20a) showed the largest immunological activity in mice with a magnitude comparable to that of levamisole and were found to be considerably less toxic than levamisole in an acute toxicological study.The structures of 18a and 20a were determined by X-ray crystallography.