Spectroscopic investigations, DFT calculations, molecular docking and MD simulations of 3-[(4-Carboxyphenyl) carbamoyl]-4-hydroxy-2-oxo-1, 2-dihydroxy quinoline-6-carboxylic acid

In this article, the synthesis, experimental vibrational spectroscopic analysis (FT-IR and FT-Raman) and theoretical calculations of Quiniline derivative 3-[(4-Carboxyphenyl) carbamoyl]-4-hydroxy-2-oxo-1, 2dihydroxy quinoline-6-carboxylic acid (CPCHODQ6C) were studied. The investigation of the IR and Raman spectra of the molecule under study, supported by DFT calculations, has afforded the opportunity to characterize explicitly the main vibrational bands for the title molecule, which is primarily used as antimalaria compound. Computational calculations were done using B3LYP/6-31G(d) basis set. Vibrational assignments of wavenumbers were performed on the basis of potential energy distribution. The downshift from the DFT value and the splitting of N-H stretching mode indicates the weakening of the N-H bond. Donor acceptor interactions were evaluated using NBO analysis. The change in polarizability values with halogen substitutions were calculated. The variations of HOMO-LUMO energy values and chemical descriptors with halogen substitutions were investigated. To foresee the important reactive sites of the title compound, we combined DFT calculations and molecular dynamics (MD) and visualized the ALIE and Fukui functions. Sensitive nature of the compound towards autoxidation and degradation in the presence of water was investigated by the calculation of BDE and RDF. By molecular docking study the compound forms a stable complex with ubiquinol-cytochrome-c reductase inhibitor.(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

This article investigates the synthesis, experimental vibrational spectroscopic analysis, and theoretical calculations of a Quiniline derivative, CPCHODQ6C. The study provides a detailed characterization of the molecule's vibrational bands and explores its potential as an antimalarial compound. Computational calculations and molecular dynamics simulations are used to analyze the compound's reactivity and sensitivity. The results highlight the compound's potential reactive sites and its tendency to undergo autoxidation and degradation in the presence of water.