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Several 2-substituted 5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido (1) and 5,6,11,11b-tetrahydro-1H-imidazo [1',5':1,2]pyrido[3,4-b]indole,3(2H)-diones (2) were synthesized and studied by 2D-NMR spectroscopy and difference nuclear Overhauser effect experiments. All the compounds were evaluated for in vitro alpha(1) adrenoceptor affinity by radioligand receptor binding assays. The most active derivative in displacement of [3H]prazosin from rat cortical membranes was 1b (K(i) = 219 nM). At 1 microM concentration, compounds 1 and 2 had no effect on the benzodiazepine or 5-HT(1A) receptor. The biological activity profile of 1b makes it a possible lead compound for the design of new selective alpha1 adrenoceptor ligands.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

.ALPHA.1-Adrenoceptor Reagents. Synthesis of Some 5,6,11,11a-Tetrahydro-1H-imidazo(1',5':1,6)pyrido and 5,6,11,11b-Tetrahydro-1H-imidazo(1',5':1,2)pyrido(3,4-b)indole-1,3(2H)-diones.