New pentadienone oxime ester derivatives: synthesis and anti-inflammatory activity

Journal of Enzyme Inhibition and Medicinal Chemistry

Hai Ping Zhou¹  Wen Jian Tang²  Liu Zeng Chen²  Jie Quan Wang²  Xin Hua Liu³  Juping Zhang⁴  Qin Li⁴  Wei Xue⁴ 

[1] School of Material Science Chemical Engineering, ChuZhou University, ChuZhou, P. R. Chin;School of Pharmacy, Anhui Province Key Laboratory of Major Autoimmune Diseases, Anhui Institute of Innovative Drugs, Anhui Medical University, Hefei, P. R. China;School of Pharmacy, Anhui Province Key Laboratory of Major Autoimmune Diseases, Anhui Institute of Innovative Drugs, Anhui Medical University, Hefei, P. R. China;School of Material Science Chemical Engineering, ChuZhou University, ChuZhou, P. R. Chin;State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Guizhou University, Guiyang, P. R. China;

关键词: Pentadienone;    oxime ester;    synthesis;    anti-inflammatory;    activity;   

DOI  :  10.1080/14756366.2017.1396455

来源: publisher

【 摘 要 】

To develop novel anti-inflammatory agents, a series of new pentadienone oxime ester compounds were designed and synthesized. The structures were determined by IR, 1H NMR, 13 C NMR, and HRMS. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition against LPS-induced nitric oxide (NO) release in RAW 264.7 cell. Among them, compound 5j was found to be one of the most potent compounds in inhibiting NO and IL-6 (IC50 values were 6.66 µM and 5.07 µM, respectively). Preliminary mechanism studies show that title compound 5j could significantly suppress expressions of nitric oxide synthase, COX-2, and NO, IL-6 through Toll-like receptor 4/mitogen-activated protein kinases/NF-κB signalling pathway. These data support further studies to assess rational design of more efficient pentadienone oxime ester derivatives with anti-inflammatory activity in the future.

【 授权许可】

CC BY