Abstract
The ability for DFT: B3LYP calculations using the 6-31g and lanl2dz basis sets to predict the electrochemical properties of twenty (20) 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives with varying degrees of cytotoxic activity in dimethylformamide (DMF) was investigated. There was a strong correlation for the first reduction and moderate-to-low correlation of the second reduction of the diazine ring between the computational and the experimental data, with the exception of the derivative containing the nitro functionality. The four (4) nitro group derivatives are clear outliers in the overall data sets and the derivative E4 is ill-behaved. The remaining three (3) derivatives containing the nitro groups had a strong correlation between the computational and experimental data; however, the computational data falls substantially outside of the expected range.
Highlights
The study of quinoxaline 1,4-di-N-oxide derivatives has been the source of worldwide interest within the last few decades, increasing over time due to their potential pharmaceutical properties that range from anti-tumor [1,2,3] to anti-trypanosomal [4,5,6]
We propose that computational methods provide a powerful tool that can predict the method of analysis
All structures for the twenty (20) 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives were drawn in GaussView 5 [30]
Summary
The study of quinoxaline 1,4-di-N-oxide derivatives has been the source of worldwide interest within the last few decades, increasing over time due to their potential pharmaceutical properties that range from anti-tumor [1,2,3] to anti-trypanosomal [4,5,6]. Research has commonly demonstrated that for homologous series the ease of reduction for quinoxaline 1,4-di-N-oxide derivatives is often correlated with increased bioactivity [6,10,11,12,13]. Previous studies have demonstrated that some quinoxaline 1,4-di-N-oxide derivatives can form radicals capable of cleaving DNA under hypoxic conditions [14,15]. This free radical mechanism is believed to cause oxidative stress at the target cells and is presumed a common underlying mechanism for the bioactivity of many quinoxaline 1,4-di-N-oxide derivatives [16,17,18,19]
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