Synthesis of novel 2-acetamidothiazoles tethered with 1,2,3-triazole and pyridine pharmacophores

Abstract

A novel series of 2-acetamidothiazoles bearing 1,2,3-triazole and pyridine moieties were designed and synthesized using simple chemical methodology. 3-Amino pyridine was converted into a potent intermediate 2-chloro-N-(4-(5-methyl-1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl)thiazol-2-yl)acetamide (5) in four steps using molecular modification approach. Heterocyclic amine(s)/ heterocyclic and aromatic thiol(s) were then introduced in 5 to obtain target compounds 6a-6i. In all, we have synthesized eleven novel molecules which have the flavor of each of these heterocyclic moieties, viz. pyridine, 1,2,3-triazole, 2-acetamido-thiazole, heterocyclic amine(s)/ heterocyclic and aromatic thiol(s). The presence of each of these bioactive moieties in a single molecular frame could be beneficial to the development of new drug candidate because these moieties together contribute to the overall resultant biological activity of the target hybrid molecule. Structure elucidation of all the newly synthesized compounds was established using IR, 1H, 13C NMR, mass spectrometry along with their elemental analyses.