Introduction of a nitrogen atom into the cyclohexane ring of 2-(4-phenylpiperidinyl) cyclohexanol (vesamicol, AH5183) yielded two positional isomers, 5-azavesamicol (5, prezamicol) and 4-azavesamicol (6, trozamicol). As inhibitors of vesicular acetylcholine transport, 5 and 6 were found to be 147 and 85 times less potent than vesamicol. N- Benzoylation of 5 (to yield 9a) increased the potency 3-fold. In contrast, loa, a compound ...
