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

Add time:07/15/2019    Source:sciencedirect.com

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.

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