Antimicrobial evaluation of diastereoisomeric 2-dimethylaminomethyl-6-phenylcyclohexanols and related esters.
2-Dimethylaminomethyl-6-phenylcyclohexanone was reduced to give the isomeric 2-dimethylaminomethyl-6-phenylcyclohexanols, which were then converted to a number of novel esters. These derivatives were screened against a wide range of microorganisms. The alcohol possessing an axial hydroxy group had high activity against Candida albicans, in contradistinction to the isomer having an equatorial hydroxy function, which was approximately 30 times less active. The esters from the isomeric alcohols demonstrated a low level of antimicrobial activity with the exception of the 10-undecenoyl ester of 2-dimethylaminomethyl-6-phenylcyclohexanol (possessing the equatorial hydroxy group), which showed significant activity against three pathogenic fungi.
D000818:Animals; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D002176:Candida albicans / Q000187:drug effects; D003511:Cyclohexanols / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D051379:Mice; D008826:Microbial Sensitivity Tests; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014234:Trichinella / Q000187:drug effects; D014249:Trichophyton / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003511:Cyclohexanols