Selective N-allylation via SN2ꞌ reaction: Synthesis, characterization, crystal structure, theoretical and biological studies of Ethyl (E)-2-(4-aminobenzene-1-sulphonylimino-thiazol-3-yl-methyl)-3-phenyl acrylate

Abstract

The title compound ethyl (E)-2-(4-aminobenzene-1-sulphonylimino-thiazol-3-yl-methyl)-3-phenyl acrylate (BH-STZ) was synthesized by an SN2ꞌ reaction between 1:1 ratio of Ethyl 2-(acetoxy phenyl-methyl) acrylate (BH) and 4-amino-N-(1,3-thiazol-2-yl) benzenesulphonamide (STZ). It was characterized by FT-IR, 1H NMR, 13C NMR, DEPT 135, Mass, elemental analysis, and SCXRD. This study investigates the selective allylation of STZ at the secondary amine nitrogen over the primary amine nitrogen. It has been confirmed by the crystal structure of BH-STZ. In the BH-STZ, the hydrogen bonding interaction between primary amine and sulphonyl oxygen (NH.O) forms the β dimer. The photophysical properties (UV absorption and fluorescence emission) of BH-STZ have been studied. The theoretical FT-IR, UV, and SCXRD calculations based on density functional theory correlated well with the experimental results. The HOMO–LUMO energy gap indicated that BH-STZ has good chemical stability and lower hardness. The in vitro antibacterial activity of BH-STZ against a panel of pathogenic bacteria was assayed by the disc diffusion method. These results were compared with molecular docking studies between BH-STZ and the respective target protein from the bacteria. The compound was shown to be non-toxic to normal cells by both in vitro (using bacterial pathogen) and in vivo (using zebrafish) studies.