Absolute configuration and local anaesthetic activity of cis and trans 2-dimethylaminomethyl-cyclohexyl benzoates.
All the four stereoisomers of 2-dimethylaminomethyl-cyclohexyl benzoate (enantiomers of 4 and 5) were prepared in optically pure state and their absolute configurations determined by chiroptical methods and genetic correlations. The configurational assignments obtained by the two independent methods were in full agreement and the absolute configuration of the four stereoisomers are (+)-(1S,2S)-4, (-)-(1R,2R)-4, (+)-(1S,2R)-5, and (-)-(1R,2S)-5. The local anaesthetic activity of the four compounds were also determined.
Nemes
P
P
Department of Chemistry, Veterinary University, Budapest, Hungary.
Kajtár
J
J
Kajtár
M
M
Kárpáti
E
E
Nádor
K
K
D000200:Action Potentials / Q000187:drug effects; D000779:Anesthetics, Local / Q000032:analysis* / Q000494:pharmacology; D000818:Animals; D001565:Benzoates / Q000032:analysis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D066298:In Vitro Techniques; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011898:Ranidae; D012584:Sciatic Nerve / Q000187:drug effects
D000779:Anesthetics, Local; D001565:Benzoates; C057721:2-dimethylaminomethylcyclohexyl benzoate