Spectroscopic , quantum chemical studies Fukui functions, in vitro anti viral activity and molecular docking of 5-cholo-N-(3-nitrophenyl)pyrazine-2-carboxamide

Journal Article

Alsenoy, S.H.R. Sebastian, M.A. Al-Alshaikh, A.A. El-Emam, C.Y. Panicker, J. Zitko, M. Dolezal, C. Van . 2016

• Publication Work Type: Research Group Project No. PRG-1436-23
• Magazine \ Newspaper: Journal of Molecular Structure (Elsevier, U.K.)
• Volume Number: 1119
• Pages: 188-199

Publication Abstract

The molecular structural parameters and vibrational frequencies of 5-chloro-N-(3-nitrophenyl)pyrazine-
2-carboxamide have been obtained using density functional theory technique in the B3LYP approximation
and CC-pVDZ (5D, 7F) basis set. Detailed vibrational assignments of observed FT-IR and FT-Raman
bands have been proposed on the basis of potential energy distribution and most of the modes have
wavenumbers in the expected range. In the present case, the NH stretching mode is a doublet in the IR
spectrum with a difference of 138 cm1 and is red shifted by 76 cm1 from the computed value, which
indicates the weakening of NH bond resulting in proton transfer to the neighboring oxygen atom. The
molecular electrostatic potential has been mapped for predicting sites and relative reactivities towards
electrophilic and nucleophilic attack. The hyperpolarizability values are calculated in order to find its role
in nonlinear optics. From the molecular docking study, amino acids Asn161, His162 forms H-bond with
pyrazine ring and Trp184, Gln19 shows H-bond with C]O group and the docked ligand, title compound
forms a stable complex with cathepsin K and the results suggest that the compound might exhibit
inhibitory activity against cathepsin K. Moderate in vitro antiviral activity with EC50 at tens of mM was
detected against feline herpes virus, coxsackie virus B4, and influenza A/H1N1 and A/H3N2.