Synthesis and quantitative structure-activity relationship analysis of 2-(aryl or heteroaryl)quinolin-4-amines, a new class of anti-HIV-1 agents

Thirty-eight 2-(aryl or heteroaryl)quinolin-4-amines, N,N-disubstituted, N-monosubstituted, and without a substituent at the amino group have been synthesized with use of novel chemistries developed by us recently. Some of these derivatives show anti-HIV-1 activity at a concentration level of 1 micr...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1991-05, Vol.34 (5), p.1739-1746
Main Authors: Strekowski, Lucjan, Mokrosz, Jerzy L, Honkan, Vidya A, Czarny, Agnieszka, Cegla, Marek T, Wydra, Roman L, Patterson, Steven E, Schinazi, Raymond F
Format: Article
Language:English
Subjects:
Antiviral Agents - chemical synthesis
Antiviral Agents - pharmacology
Chemical Phenomena
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
HIV-1 - drug effects
Organic chemistry
Preparations and properties
Quinolines - chemical synthesis
Quinolines - pharmacology
Structure-Activity Relationship
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Summary:Thirty-eight 2-(aryl or heteroaryl)quinolin-4-amines, N,N-disubstituted, N-monosubstituted, and without a substituent at the amino group have been synthesized with use of novel chemistries developed by us recently. Some of these derivatives show anti-HIV-1 activity at a concentration level of 1 microM and low cell toxicity in vitro. The most active and least toxic compounds are derivatives of 2-(3-pyridyl)quinoline. The results of the quantitative structure-activity relationship analyses, including several classical, linear regression correlations and a Free-Wilson approach of de novo model, provide guidelines for the design of new active compounds of this class.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00109a031