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

Autor: Miller EM; Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA. emmiller1s@semo.edu., Xia Q; Department of Pharmacology, Ningbo College of Health Sciences, No. 51, Xuefu Road, Yinzhou, Ningbo 315000, China. sunnyxq@zju.edu.cn., Cella ME; Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA. tomariahcella@gmail.com., Nenninger AW; Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA. anenninger@health.usf.edu., Mruzik MN; Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA. mnmruzik@semo.edu., Brillos-Monia KA; Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA. kbrillos8@gmail.com., Hu YZ; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China. huyz@zju.edu.cn., Sheng R; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China. shengr@zju.edu.cn., Ragain CM; Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA. cragain@semo.edu., Crawford PW; Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701, USA. pcrawford@semo.edu.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2017 Aug 31; Vol. 22 (9). Date of Electronic Publication: 2017 Aug 31.
DOI: 10.3390/molecules22091442
Abstrakt: 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.
Competing Interests: The authors declare no conflict of interest.
Databáze: MEDLINE
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