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Design, synthesis, and DNA-binding of N-alkyl(anilino)quinazoline derivatives.

Abstract：

:New N-alkylanilinoquinazoline derivatives 5, 12, 20, and 22 have been prepared from 4-chloro-6,7-dimethoxyquinazoline 3, 4-chloro-6,7-methylenedioxyquinazoline 19, and commercially available anilines. Differents classes of compounds substituted by an aryloxygroup (6a-c, 16a,b, and 17a,b), (aminophenyl)ureas (12a,b and 13a-f), anilines (4a-m, 20a,b), N-alkyl(aniline) (5a-m, 21a,b, 22a,d), and N-aminoalkyl(aniline) (22e-g) have been synthesized. These molecules were evaluated for their cytotoxic activities and as potential DNA intercalating agents. We studied the strength and mode of binding to DNA of these molecules by DNA melting temperature measurements, fluorescence emission, and circular dichroism. The results of various spectral and gel electrophoresis techniques obtained with the different compounds, in particular compounds 5g and 22f, revealed significant DNA interaction. These experiments confirm that the N-aminoalkyl(anilino)-6,7-dimethoxyquinazoline nucleus is an efficient pharmacophore to trigger binding to DNA, via an intercalative binding process.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Garofalo A,Goossens L,Baldeyrou B,Lemoine A,Ravez S,Six P,David-Cordonnier MH,Bonte JP,Depreux P,Lansiaux A,Goossens JF

doi

10.1021/jm1009605

subject

Has Abstract

pub_date

2010-11-25 00:00:00

pages

8089-103

issue

22

eissn

0022-2623

issn

1520-4804

journal_volume

53

pub_type

杂志文章

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