Molecules (Aug 2002)

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

  • Tom Ellis,
  • Mohamed Bouakka,
  • Abdelkader Hakkou,
  • Sghir Elkadiri,
  • Rachid Touzani,
  • Abdelkrim Ramdani,
  • Ann T. Kotchevar,
  • Taibi Ben-Hadda,
  • Michael J. Waring

DOI
https://doi.org/10.3390/70800641
Journal volume & issue
Vol. 7, no. 8
pp. 641 – 656

Abstract

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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.

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