New adamantan-2-ol and adamantan-1-methanol derivatives as potent antibacterials. Synthesis, antibacterial activity and lipophilicity studies

Two series of active adamantane-group-bearing trialkylamines and their quaternary ammonium salts were synthesized and their biological properties were tested. One series includes 2-(3-dialkylaminopropyl)tricyclo[3.3.1.1(3,7)] decan-2-ols and the other alpha,alpha-bis(3-dialkylaminopropyl)tricyclo[3.3.1.1(3,7)]decyl/1-methanols. Some of the synthesized molecules proved to be very active anti bacterials. The minimum inhibitory concentration (MIG) values of the most potent compounds were determined. The observed differences were investigated. The antibacterial activity of the compounds was found to be enhanced as the length of the nitrogen-attached carbon chain extends from CH3 to C12H25. The lipophilicity of the synthesized molecules was also studied and its relationship with the antibacterial activity was investigated.