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Molecules 2017, 22(9), 1442; doi:10.3390/molecules22091442

Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities

1
Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA
2
Department of Pharmacology, Ningbo College of Health Sciences, No. 51, Xuefu Road, Yinzhou, Ningbo 315000, China
3
College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 9 August 2017 / Revised: 28 August 2017 / Accepted: 29 August 2017 / Published: 31 August 2017
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

The electrochemical properties of twenty 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives with varying degrees of cytotoxic activity were investigated in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. With one exception, the first reduction of these compounds was found to be reversible or quasireversible and is attributed to reduction of the N-oxide moiety to form a radical anion. The second reduction of the diazine ring was found to be irreversible. Compounds containing a nitro group on the 3-phenyl ring also exhibited a reduction process that may be attributed to that group. There was good correlation between molecular structure and reduction potential, with reduction being facilitated by an enhanced net positive charge at the electroactive site created by electron withdrawing substituents. Additionally, the reduction potential was calculated using two common basis sets, 6-31g and lanl2dz, for five of the test molecules. There was a strong correlation between the computational data and the experimental data, with the exception of the derivative containing the nitro functionality. No relationship between the experimentally measured reduction potentials and reported cytotoxic activities was evident upon comparison of the data. View Full-Text
Keywords: quinoxaline-di-N-oxide derivatives; voltammetry; anti-tumor; reduction potential; experimental and computational quinoxaline-di-N-oxide derivatives; voltammetry; anti-tumor; reduction potential; experimental and computational
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Miller, E.M.; Xia, Q.; Cella, M.E.; Nenninger, A.W.; Mruzik, M.N.; Brillos-Monia, K.A.; Hu, Y.Z.; Sheng, R.; Ragain, C.M.; Crawford, P.W. Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities. Molecules 2017, 22, 1442.

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