Synthesis, spectral analysis and anti-bacterial study of N-substituted derivatives of 2-(5-(1-(phenylsulfonyl)piperidin-4-yl)-1,3,4-oxadiazol-2-ylthio)acetamide

Abstract

1,3,4-Oxadiazole bearing compounds are one of the most attractive class for researchers due to their biological activities. In the undertaken research, a number of N-substituted derivatives of 2-(5-(1-(phenylsulfonyl)piperidin-4-yl)-1,3,4-oxadiazol-2-ylthio)acetamide (6a–n) were synthesized through a series of steps. The reaction of benzenesulfonyl chloride with ethyl isonipecotate yielded ethyl 1-(phenylsulfonyl)piperidin-4-carboxylate (1), which was further converted into 1-(phenylsulfonyl)piperidin-4-carbohydrazide (2) and 5-(1-(phenylsulfonyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol (3) respectively. The target compounds 6a–n were synthesized by the reaction of compound 3 with different N-aralkyl/aryl substituted 2-bromoacetamides (5a–n) in the presence of a weak base and polar aprotic solvent. The structures of the synthesized compounds were elucidated through 1H-NMR, IR and mass spectral data. The synthesized compounds were screened against Gram-negative and Gram-positive bacteria and exhibited moderate to talented activity.

Keywords

• Ethyl isonipecotate
• Acetamides
• 1,3,4-Oxadiazole
• IR
• 1H-NMR
• EIMS