Design, synthesis, characterization, bio-molecular docking studies, and biological activity of (4-amino-2-(aryl/alkylamino)thiazol-5-yl)(6-methylbenzo[d] thiazol-2-yl)methanone derivatives

Abstract

A series of novel (4-amino-2-(aryl/alkylamino)thiazol-5-yl)(6-methylbenzo[d]thiazol-2-yl)methanone compounds have been synthesized. They have been characterized by elemental analysis, IR, ¹H and ¹³C NMR and mass spectral techniques. All the synthesized compounds have been screened for their antibacterial potential and show significant antibacterial activity. Among these (4-amino-2-(4-chlorophenyl)amino)thiazol-5-yl)(6-methylbenzo[d]thiazol-2-yl)methanone is more active. Moreover, the compound 3d shows promising antioxidant activity activity. The compounds have been further evaluated for their potential for DNA cleavage and two compounds completely cleaved DNA. Two of the compounds have been evaluated for their anti-proliferative activity against breast cancer cell lines. The IC₅₀ value of the compound (4-amino-2-(4-chlorophenyl)amino)thiazol-5-yl)(6-methylbenzo[d]thiazol-2-yl)methanone against the cell line MCF-7 is found to be 10 µg/mL. Four compounds have been docked towards 5077 receptor protein. Molecular docking shows very good interaction with protein. In this (4-amino-2-(4-methoxyphenyl)amino)thiazol-5-yl)(6-methylbenzo[d]thiazol-2-yl)methanone has the highest binding interaction with the protein.