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

Michael Waring, Taibi Ben-Hadda, Ann Kotchevar, Abdelkrim Ramdani, Rachid Touzani, Sghir Elkadiri, Abdelkader Hakkou, Mohamed Bouakka, Tom Ellis
2002 Molecules  
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
more » ... derivatives. However, subtle alteration by addition of a nitro group affecting the charge distribution confers significant improvements in biological effects and binding to DNA.
doi:10.3390/70800641 fatcat:nolmcyaoqvaxxfo42tsvcdvn2a