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A series of six aromatic esters of both 5-dimethyl-amino-1-phenyl-3-pentanol and 3-dimethylamino-1-(2-phenylcyclohexyl)-1-propanol was prepared. Antimicrobial evaluation showed that the cyclic analogs had approximately twice the activity of the open chain series; in particular, the o-chlorophenyl ester showed pronounced activity against three pathogenic fungi at approximately 10 ppm. Aromatic esters of 3-dimethylamino-1-phenyl-1-propanol were prepared and demonstrated lower activity than two esters of 2-dimethylamino-1-phenylcyclohexanol. The screening results showed that the best activity was found when a dimethylene chain was present between the phenyl ring and the carbon atom bearing the acyloxy function and that the cyclic derivatives were more active than their more flexible counterparts.
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