Recently, we have recently reported experimental and preliminary computational electrochemical properties of twenty 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives with varying degrees of cytotoxic activity. Experimentally, the quinoxaline derivatives were investigated in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry and with only one exception, the first reduction of these compounds was found to be reversible or quasireversible. The reversibility is attributed to reduction of the N-oxide moiety to form a radical anion. However, the second reduction of the diazine ring was found to be irreversible as the dianion compound forms a stable double bonded compound. Five of the compounds contained a nitro group on the 3-phenyl ring and also exhibited a reduction process that may be attributed to the nitro group. The preliminary computational experiments calculated the reduction potential for 5 test molecules. The computational experiments using Gaussian 09 and GaussView 5 have investigated the ability of 6-31g and lanl2dz to accurately predict the experimental electrochemical properties. With the exception of the test molecule containing the nitro group, there was a strong correlation between the computational data and the experimental data. In contrast to previous studies of quinoxaline derivatives, no relationship between the experimentally measured (or computational calculated) reduction potentials and reported cytotoxic activities was observed upon comparison of the data sets.

Voltammetric and preliminary computational study of 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxidide derivatives with anti-tumor properties

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.