Synthesis and immunological activity of 5,6,6a,8,9,11a-hexahydronaphth[1',2':4,5]imidazo[2,1-b]thiazoles and 5,6,6a,9,10,11a-hexahydronaphth[2',1':4,5]imidazo[2,1-b]thiazoles

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Abstract
A series of 5,6,6a,8,9,11a-hexahydronaphth[1'',2'':4,5]imidazo[2,1-b]thiazoles and 5,6,6a,9,10,11a-hexahydronaphth[2'',1'':4,5]imidazo[2,1-b]thiazoles was synthesized with cis- and/or trans-1,2-diamino-1,2,3,4-tetrahydronaphthalenes 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 and (.+-.)-5,6,6a.beta.,8,9,11a.alpha.-hexahydro-8.beta.-hydroxy-9.beta.-methyl-8.alpha.-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 considerably less toxic than levamisole in an acute toxicological study. The structures of [trans-5,6,6a,9,10,11a-hexahydronaphth[2'',1'':4,5]imidazo[2,1-b]thiazole] and 20a were determined by X-ray crystallography.