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

Journal of Saudi Chemical Society

Muhammad Ashraf¹  Muhammad Athar Abbasi²  Ambreen Fatima²  Aziz-ur-Rehman²  Shahid Rasool²  Irshad Ahmad³  Syeda Abida Ejaz³  Abdul Malik⁴ 

[1] Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan;Department of Chemistry, Government College University, Lahore 54000, Pakistan;Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan;HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan;

关键词: Organic acids;    Oxadiazoles;    Lipoxygenase;    Spectral analysis;    1H-NMR;    IR and EI-MS;   

DOI  :  10.1016/j.jscs.2013.02.006

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown