Synthesis and antimicrobial studies of new pyridine derivatives

Abstract

2-(p-Acetylaminobenzenesulfonylamido)-substituted benzothiazoles were prepared from 2-amino-substituted benzothiazoles and p-acetamidobenzenesulfonyl chloride using a mixture of pyridine and Ac2O, which formed an electrophilic N-acetyl- pyridinium complex facilitating condensation to give the desired products by removal of HCl. 2-[4-(Substituted benzothiazol-2-yl)aminosulfonylanilino]pyridine-3-carboxylic acids (synthesized from 2-chloropyridine-3-carboxylic acid and the corresponding substituted 2-(p-aminobenzenesulfonylamido)benzothiazole in 2-ethoxyethanol using Cu-powder and K2CO3) were then converted to acid chlorides, which on further reaction with piperazine and 4-methoxyphenylpiperazine yielded the corresponding 2-[4-(substituted benzothiazol-2-yl)amino-sulfonyl]anilino-3-(piperazinocarbonyl) pyridine and 2-[4-(substituted benzothiazol-2-yl)amino-sulfonyl]anilino-3-[(4-methoxyphenyl)piperazin-1-yl-carbonyl]pyridine. The structures of the new compounds have been established on the basis of their elemental analyses as well as IR, 1H NMR, and mass-spectral data. All the compounds have been screened for antimicrobial activity and found to possess considerable antibacterial activity.