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

• Main Authors: Aziz-ur-Rehman, Ambreen Fatima, Muhammad Athar Abbasi, Shahid Rasool, Abdul Malik, Muhammad Ashraf, Irshad Ahmad, Syeda Abida Ejaz
• Format: Article
• Language: English
• Published: Elsevier 2016-09-01
• Series: Journal of Saudi Chemical Society
• Subjects: Organic acids; Oxadiazoles; Lipoxygenase; Spectral analysis; 1H-NMR; IR and EI-MS
• Online Access: http://www.sciencedirect.com/science/article/pii/S1319610313000197

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.