Comparison of antimicrobial activity of nuclear-substituted aromatic esters of 5-dimethylamino-1-phenyl-3-pentanol and 3-dimethylamino-1-phenyl-1-propanol with related cyclic analogs.
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.
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D004353:Drug Evaluation, Preclinical; D004952:Esters / Q000138:chemical synthesis; D007659:Ketones / Q000494:pharmacology; D009574:Nitro Compounds / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000605:Amino Alcohols; D000900:Anti-Bacterial Agents; D004952:Esters; D007659:Ketones; D009574:Nitro Compounds