Synthesis, Spectral Analysis and Biological Evaluation of Sulfonamides Bearing Piperidine Nucleus

Abstract

In the current study, two new series of N-alkyl-N-(piperidin-1-yl)benzenesulfonamide (3a-f) and N-aryl substitued 2-[(phenylsulfonyl)-(piperidin-1-yl)amino]acetamide (5a-c) were synthesized and enzyme inhibiting activity was screened for all these chemical entities. The synthesis was carried out by the coupling of benzenesulfonyl chloride (a) with 1-amino piperidine (b) under dynamic pH control in aqueous media to afford parent compound N-(piperidin-1-yl)benzenesulfonamide (1). The parent compound further on treatment with different electrophiles 2a-f and 4a-c in the presence of sodium hydride (NaH) and N,N-dimethyl formamide furnished 3a-f and 3a-c derivatives, respectively. The structures of all the synthesized compounds were confirmed based on IR, EIMS and ¹H NMR data. The synthesized compounds were screened against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX) enzymes and almost all the compounds exhibited promising activity but some of the compounds remained inactive against lipoxygenase enzymes.