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Conformational studies of a family of related antimalarial phenanthrene amino alcohols.

Authors
Type
Published Article
Journal
Journal of medicinal chemistry
Publication Date
Volume
20
Issue
1
Pages
103–106
Identifiers
PMID: 319232
Source
Medline
License
Unknown

Abstract

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.

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