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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 (CC BY 3.0).
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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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