Relationship between electronic properties and drug activity of seven quinoxaline compounds: A DFT study

• Quantum descriptors of 13 quinoxalines were calculated.
• The quantum descriptors are correlated with the biological activity.
• Six new quinoxaline were suggested with possible more activity.
• Both oxygen of quinoxalines are involved in the mechanism.

The quantum chemical calculations at the DFT/B3LYP level of theory were carried out on seven quinoxaline compounds, which have been synthesized as anti-Mycobacterium tuberculosis agents. Three conformers were optimized for each compound and the lowest energy structure was found and used in further calculations. The electronic properties including EHOMO, ELUMO and related parameters as well as electron density around oxygen and nitrogen atoms were calculated for each compound. The relationship between the calculated electronic parameters and biological activity of the studied compounds were investigated. Six similar quinoxaline derivatives with possible more drug activity were suggested based on the calculated electronic descriptors. A mechanism was proposed and discussed based on the calculated electronic parameters and bond dissociation energies.

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