Synthesis, Spectroscopic Characterization, Biological Activities, X-Ray Diffraction and Molecular Docking Studies of 2-Methyl

Abstract

We performed a different methodology for amide bond formation, the 2-methyl-3-(thiazol-2-ylcarbamoyl)phenylacetate (MTP) compound, which was prepared from the reaction of 3-acetoxy-2-methylbenzoic anhydride with thiazol-2-amine. The MTP compound was characterized with the assistance of various spectral techniques including IR, 1 H NMR, C-13 NMR, XRD and elemental analysis. The MTP has been crystallized in the monoclinic space group P2(1) /n. The ground state molecular structure (GSMS) of the optimized MTP was obtained using the DFT/B3LYP/6-31G(d,p) method. Then, intermolecular interactions for the MTP crystal were conducted by the 2D and 3D Hirshfeld analyses. Next, the DFT-optimized structure of MTP compound was used to perform molecular docking studies with the pr-teins of bacterial and fungal organisms in order to find the most preferred binding mode of ligand within the protein cavity. Druglikeness assay, ADME and Toxicology studies have been carried out to predict whether the MTP has an effective drug characteristics or not. The antimicrobial activity of the MTP was tested in terms of antibacterial and antifungal activities. The results revealed that this MTP showed the best activity against B. licheniformis among four bacterial species and A. flavus and C. utilis among five fungal species. These findings indicate that this and similar compounds with thiazole ring can be used as antibacterial agents in the future.(C) 2022 Elsevier B.V. All rights reserved.