Recent Advances in the Synthesis of Conveniently Substituted Flavones, Quinolones, Chalcones and Aurones: Potential Biologically Active Molecules

Authors: Hadjeri M.; Beney C.; Boumendjel A.

Source: Current Organic Chemistry, Volume 7, Number 7, May 2003 , pp. 679-689(11)

Publisher: Bentham Science Publishers

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Abstract:

Conveniently substituted flavones, chalcones and quinolones are highly attractive derivatives due to their therapeutic potential. The substitution pattern of these compounds is crucial for their biological activity. Literature survey regarding the structure-activity relationship of flavone, indicates that: azaflavones are highly active molecules; the 5 and 7 positions are the most important; hydroxyls, methoxy and amino groups are the most beneficial. In this manuscript, we report a general methodology to synthesize conveniently substituted azaflavones: (aminoflavones, 2-phenyl-4-quinolones, 3-phenyl-4- quinolones, aminochalcones and azaaurones) which fulfill these structural criteria. The methodology described implies the same starting and commercially available material: 3,5-dimethoxyaniline. Finally, we report some unusual reactivity behavior of amides derived from 3,5-dimethoxyaniline.

Keywords: flavones; quinolones; chalcones; aurones; aminoflavones; 2-phenyl-4-quinolones; 3-phenyl-4- quinolones; aminochalcones; 3,5-dimethoxyaniline

Language: English

Document Type: Review article

DOI: http://dx.doi.org/10.2174/1385272033486765

Publication date: 2003-05-01