ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis, crystal structures, and theoretical studies on bio-pertinent disulfides derived from methyl thiosalicylate and furan-2-thiocarboxylic acid and their interaction with native human lysozymes

Krishna Kumar, Anil Kumar Vishwkarma, Rajesh Pratap, Somenath Garai, Amit Pathak, Rohit Sharma, and Subrato Bhattacharya

Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, India

E-mail: s_bhatt@bhu.ac.in

Received: 14 February 2023  Accepted: 23 January 2024

Abstract:

Aromatic substituted thiol and aromatic 2-furoylthiocarboxylic acid were catalytically oxidized into corresponding disulfides, dimethyl 2,2'-disulfanediyldibenzoate (1) and furan-2-carboxylic dithioperoxyanhydride (3) have been characterized by single crystal X-ray analysis. Methylene insertion (gas phase) into the disulfide linkage was studied in both molecules. We have performed extensive docking studies of the interaction with Native Human Lysozyme and found that 3 exhibits better binding efficiencies with Native Human Lysozyme compared to compound 1. Hirshfeld analyses were made to study the type of weak interactions quantitatively. The thermal and electronic stabilities of these compounds have been studied using Density functional theory calculations. Natural bond orbital analyses have been used to find out hyper-conjugative energies, highest occupied molecular orbitals- Lowest unoccupied molecular orbital along with electronic transitions. We have also investigated the thermal stabilities of molecules as well as the vibrational contribution in the thermodynamic parameters such as specific heat, Gibb’s free energy, and entropy at different temperatures.

Keywords: Crystal structure; Docking; Disulfide linkage; Thermodynamic property

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-024-03342-4

Chemical Papers 78 (6) 3721–3733 (2024)