4-Amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function
- 31 March 1981
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 24 (4) , 404-408
- https://doi.org/10.1021/jm00136a010
Abstract
The effect on potency of modification of the carbonyl function of analgesics derived from 4-(dimethylamino)-4-arylcyclohexan-1-one was studied by reduction and by addition of nucleophiles. The resulting amino alcohols were separated and assigned structures on the basis of X-ray crystallography, NMR and TLC mobility. The trans (OH and N) isomers were invariably more potent than the cis. Inclusion of flat lipophilic moieties (phenyl, cyclohexenyl) at a distance of at least 2 C atoms from the C bearing hydroxyl led to increases in potency by orders of magnitude. The possible significance of this on receptor interaction is discussed. Analgesic activity was tested in mice.This publication has 1 reference indexed in Scilit:
- 4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ringJournal of Medicinal Chemistry, 1980