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Molecules 2002, 7(8), 641-656; doi:10.3390/70800641
Article

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

4, 1,* , 3, 1, 1, 1, 2, 2 and 4
1 Department of Chemistry, Faculty of Sciences, University Mohammed 1er, Oujda 60000, Morocco 2 Department of Biology, Faculty of Sciences, University Mohammed 1er, Oujda 60000, Morocco 3 Department of Chemistry and Biochemistry, 1 University Plaza, Long Island University, Brooklyn, NY 11201, USA 4 Department of Pharmacology, University of Cambridge, Tennis Court Road, Cambridge, CB2 1QJ, UK
* Author to whom correspondence should be addressed.
Received: 13 February 2002 / Revised: 8 August 2002 / Accepted: 10 August 2002 / Published: 30 August 2002
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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.
Keywords: Dissymmetric quinoxalines; DNA intercalator; Bayoud; Tuberculosis; Cancer Dissymmetric quinoxalines; DNA intercalator; Bayoud; Tuberculosis; Cancer
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Waring, M.J.; Ben-Hadda, T.; Kotchevar, A.T.; Ramdani, A.; Touzani, R.; Elkadiri, S.; Hakkou, A.; Bouakka, M.; Ellis, T. 2,3-Bifunctionalized Quinoxalines: Synthesis, DNA Interactions and Evaluation of Anticancer, Anti-tuberculosis and Antifungal Activity. Molecules 2002, 7, 641-656.

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