Conformational studies of a family of related antimalarial phenanthrene amino alcohols.
A conformational study utilizing quantum chemical methods was performed on a family of antimalarial alpha-(piperidyl)-3,6-bis(trifluoromethyl)-9-phenanthrenemethanols whose structures differ by the placement of the substituent on either the 2,3, or 4 position of the piperidyl ring. The antimalarial activity of these 3-substituted compounds has been shown experimentally to be highly stereospecific while the 2-substituted compounds are not and the 4-substituted compounds are inactive. In this study, such observed differences in behavior are correlated with conformational results and a pharmacophore is postulated. The identity of the active racemate of the 3-piperidyl compound is predicted.
D000605:Amino Alcohols; D000962:Antimalarials / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D008968:Molecular Conformation; D010616:Phenanthrenes; D010880:Piperidines; D010962:Plasmodium berghei / Q000187:drug effects; D013237:Stereoisomerism
D000605:Amino Alcohols; D000962:Antimalarials; D010616:Phenanthrenes; D010880:Piperidines