Synthesis, characterization and biological screening of N-substituted derivatives of 5-benzyl-1,3,4-oxadiazole-2yl-2''-sulfanyl acetamide

ABSTRACT

A series of new N-substituted derivatives of 5-benzyl-1, 3, 4-oxadiazole-2yl-2''-sulfanyl acetamide [6a-n] were synthesized in three phases. The first phase involved the sequentially converting phenyl acetic acid into ester, hydrazide and finally cyclized in the presence of CS[2] to afford 5-benzyl-1, 3, 4-oxadiazole-2-thiol. In the second phase N-substituted-2-bromoacetamides were prepared by reacting substituted amines with bromoacetyl bromide in basic media. In the third phase, 5-benzyl-1,3,4-oxadiazole-2-thiol was stirred with N-substituted-2-bromoacetamides in the presence of N,N-dimethyl formamide [DMF] and sodium hydride [NaH] to get the target compounds. Spectral techniques were used to confirm the structures of synthesized compounds. Synthesized compounds were screened against butyrylcho linesterase [BChE], acetylcholinesterase [AChE], and lipoxygenase enzymes [LOX] and were found to be relatively more active against acetylcholinesterase