Design, synthesis and structure–activity relationship of indoxacarb analogs as voltage-gated sodium channel blocker. Issue 20 (15th October 2015)

• Record Type: Journal Article
• Authors: Hao, Wenbo; Fu, Chunling; Yu, Huijuan; Chen, Jian; Xu, Hanhong; Shao, Guang; Jiang, Dingxin
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 25:Issue 20(2015)
• Page Start: 4576
• Page End: 4579
• Publication Date: 2015-10-15
• Subjects: Indoxacarb analogs -- Synthesis -- Sodium channel blocker -- Structure–activity relationships; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.08.058
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Indoxacarb, the first commercialized pyrazoline-type sodium-channel blocker, is a commonly used insecticide because of high selectivity. To discover sodium-channel blocker with high insecticidal activity, a series of novel indoxacarb analogs were designed and synthesized by judicious structural modifications of the substituent group of C5, C6 in indenone and C′4 in benzene ring. Some analogs exhibited significant insecticidal activities against Spodoptera litura F. and excellent BgNav1-1a channel inhibitory activity. The structure–activity analysis indicated that the presence of strong electron-withdrawing group and decreased steric hindrance of indenone ring (R 1, R 2 ) in 5- and 6-position could enhance larvicidal activity and BgNav1-1a channel inhibitory activity.