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

Michael J. Waring 4 , Taibi Ben-Hadda 1,* email, Ann T. Kotchevar 3 , Abdelkrim Ramdani 1 , Rachid Touzani 1 , Sghir Elkadiri 1 , Abdelkader Hakkou 2 , Mohamed Bouakka 2  and Tom Ellis 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; in revised form: 8 August 2002 / Accepted: 10 August 2002 / Published: 30 August 2002
PDF Full-text Download PDF Full-Text [164 KB, uploaded 3 October 2008 10:47 CEST]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert