Synthesis, spectroscopic investigations, quantum chemical studies, molecular docking and antiviral activity of 5-chloro-N-(2-chlorophenyl)pyrazine-2-carboxamide

Journal Article

Dolesal, S. H. Rosline Sebastian, Monirah A. Al-Alshaikh, Ali A. El-Emam, Sheena Mary Y, C. Yohannan Panicker,*, P. J. Jojo, Jan Zitko, Martin . 2016

• Magazine \ Newspaper: Science Advances Today
• Issue Number: 25239
• Volume Number: 2
• Pages: 1-11

Publication Abstract

The FT-IR and FT-Raman spectra of 5-chloro-N-(2-chlorophenyl)pyrazine-2-carboxamide were recorded and the vibrational wavenumbers are computed using DFT method. On the basis of potential energy distribution the complete vibrational assignments were performed. From the molecular electrostatic potential study the negative potential regions are mainly localized over the carbonyl group and phenyl ring and are possible sites for electrophilic attack. The calculated HOMO and LUMO energies confirm that charge transfer occurs within the molecule. The geometrical parameters of the title compound are in agreement with that of similar compounds. The calculated first hyperpolarizability value is comparabel with that of similar derivatives and the study of second hyperpolarizability reveals that the title compound is an attractive object for future studies in nonlinear optics. From the molecular docking study, the docked ligand title compound forms a stable complex with glucosamine 6-phosphate deaminase from E.coli and gives a binding affinity value of -6.4kcal/mol. The results suggest that the compound might exhibit inhibitory activity against glucosamine 6-phosphate deaminase. The title compound was tested for in vitro activity against various DNA and RNA viruses, but no activity was observed.