Synthesis of new N-(5-chloro-2-methoxyphenyl)-4-(5-substituted-1,3,4-oxadiazol-2-ylthio)butanamide derivatives as suitable lipoxygenase inhibitors

Heterocyclic compounds are the most attractive class for researchers due to their biological activities. In the undertaken research, a number of N-(5-chloro-2-methoxyphenyl)-4-(5-substituted-1,3,4-oxadiazol-2-ylthio)butanamide (6a-k) compounds were prepared by converting multifarious phenyl/aryl/aralkyl/heterocyclic organic acids (1a-k) consecutively into the corresponding esters (2a-k), hydrazides (3a-k) and 5-substituted-1,3,4-oxadiazol-2-thiols (4a-k). Finally, the target compounds 6a-k were synthesized by stirring 5-substituted-1,3,4-oxadiazol-2-thiols (4a-k) with N-(5-chloro-2-methoxyphenyl)-4-bromobutanamide (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride (NaH). The structure elucidation of the synthesized compounds was processed through 1H-NMR, IR and mass spectral data. The synthesized compounds were screened against lipoxygenase enzyme (LOX) and showed moderately good activities relative to the reference standard Baicalein.