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2,3-Bifunctionalized Quinoxalines: Synthesis, DNA Interactions and Evaluation of Anticancer, Anti-tuberculosis and Antifungal Activity

Author(s): Michael J. Waring | Taibi Ben-Hadda | Ann T. Kotchevar | Abdelkrim Ramdani | Rachid Touzani | Sghir Elkadiri | Abdelkader Hakkou | Mohamed Bouakka | Tom Ellis

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 8; Start page: 641; Date: 2002;
Original page

Keywords: Dissymmetric quinoxalines | DNA intercalator | Bayoud | Tuberculosis | Cancer

ABSTRACT
A variety of 2,3-bifunctionalized quinoxalines (6-14) have been prepared by the condensation of 1,6-disubstituted-hexan-1,3,4,6-tetraones (1-4) with o-phenylenediamine, (R,R)-1,2-diaminocyclohexane and p-nitro-o-phenylenediamine. It is concluded that strong intramolecular N-H----O bonds in the favoured keto-enamine form may be responsible for the minimal biological activities observed in DNA footprinting, antitubercular, anti-fungal and anticancer tests with these hyper π-conjugated quinoxaline derivatives. However, subtle alteration by addition of a nitro group affecting the charge distribution confers significant improvements in biological effects and binding to DNA.