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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

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Received: 13 February 2002; in revised form: 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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MDPI and ACS Style

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.

AMA Style

Waring MJ, Ben-Hadda T, Kotchevar AT, 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(8):641-656.

Chicago/Turabian Style

Waring, Michael J.; Ben-Hadda, Taibi; Kotchevar, Ann T.; Ramdani, Abdelkrim; Touzani, Rachid; Elkadiri, Sghir; Hakkou, Abdelkader; Bouakka, Mohamed; Ellis, Tom. 2002. "2,3-Bifunctionalized Quinoxalines: Synthesis, DNA Interactions and Evaluation of Anticancer, Anti-tuberculosis and Antifungal Activity." Molecules 7, no. 8: 641-656.


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