Noncovalent interaction analysis and bioactivity evaluation of a novel chlorinated Schiff compound

Udaya Kumar, A. H. and Mr, Mahesha and Pampa, K. J. and Nanishankar, V. Harohally and Sneha, Yadav and Ragesh Nath, R. and Shivaraju, Harikaranahalli Puttaiah and Lokanath, N. K. (2025) Noncovalent interaction analysis and bioactivity evaluation of a novel chlorinated Schiff compound. Journal of Biomolecular Structure and Dynamics. pp. 1-12.

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Abstract

Intermolecular interactions play a significant role in the area of pharmaceuticals. Hence, there is an increasing trend towards the analysis of noncovalent interactions of active molecules to investigate the correlation between structure and properties. In this context, new Schiff base compound 2,4- dichloro-6-(((4-chlorobenzyl)imino)methyl)phenol has been prepared by condensation of 3,5-dichloro-2- hydroxybenzaldehyde and (4-chlorobenzyl)methenamine. The single crystals of Schiff base were obtained by the slow evaporation method. To investigate the solid-state behaviour and noncovalent interactions, X-ray diffraction analysis was performed. The crystal packing pattern is evident that non- covalent C–H‧‧‧O, C–H‧‧‧p and p‧‧‧p interactions result in 2-D supramolecular architecture. Meanwhile, computational studies were carried out to rationalize the strength and nature of different types of interactions involved in the crystal packing. Hirshfeld surface and enrichment ratio analyses provide the quantitative contribution of each intermolecular interaction. The intramolecular hydrogen bonding environment is well supported qualitatively by QTAIM and NCI isosurface. Based on the opti- mized ground state geometry by density functional theory, the physical and chemical properties of the compound were investigated. To acquire a more profound comprehension of the interaction of the ligand with the protein and their binding affinity, in-silico docking and molecular dynamic simula- tion studies were performed. It has also been observed that the Schiff base compound unveiled anti- bacterial activity against the bacterial species MRSA.

Item Type:	Article
Uncontrolled Keywords:	Schiff base; crystal structure; enrichment ratio; DFT studies; docking; molecular dynamics
Subjects:	500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 24 Organic Chemistry
Divisions:	Plantation Products Spices and Flavour Technology
Depositing User:	Somashekar K S
Date Deposited:	28 Nov 2025 09:34
Last Modified:	28 Nov 2025 09:34
URI:	http://ir.cftri.res.in/id/eprint/20129

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