Anthranilic diamides derivatives as potential ryanodine receptor modulators: Synthesis, biological evaluation and structure activity relationship. Issue 12 (23rd July 2018)

• Record Type: Journal Article
• Authors: Liu, Jing-Bo; Li, Feng-Yun; Dong, Jing-Yue; Li, Yu-Xin; Zhang, Xiu-Lan; Wang, Yuan-Hong; Xiong, Li-Xia; Li, Zheng-Ming
• Is Part Of: Bioorganic & medicinal chemistry. Volume 26:Issue 12(2018)
• Page Start: 3541
• Page End: 3550
• Publication Date: 2018-07-23
• Subjects: N-Phenylpyrazole -- Ryanodine receptor modulator -- Insecticidal activity -- DFT; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2018.05.028
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Highlights: Novel anthranilic diamides derivatives 7a–s were designed and synthesized. Most of title compounds showed moderate to excellent insecticidal activities. The insecticidal activity of 7o was comparable to that of chlorantraniliprole. Ryanodine receptor is the possible target of title compounds. Abstract: A series of novel anthranilic diamides derivatives (7a–s ) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point, 1 H NMR, 13 C NMR and elemental analyses. The bioactivity revealed that most of them showed moderate to excellent activities against oriental armyworm ( Mythimna separata ) and diamondback moth ( Plutella xylostella ). Above all, the larvicidal activity of 7o against oriental armyworm was 100% and 40% at 0.25 and 0.1 mg L −1, comparable to that of the standard chlorantraniliprole (100%, 0.25 mg L −1 and 20%, 0.1 mg L −1 ). What is more, 7o against diamondback moth displayed 90% insecticidal activity at 0.01 mg L −1, superior to chlorantraniliprole (45%, 0.01 mg L −1 ). The experiments 7o on the American cockroach (Periplaneta Americana) heart beating rates (Dorsal vessel) and contractile force were compared with chlorantraniliprole. In addition, 7o could affect the calcium homeostasis in the central neurons of the third larvae of oriental armyworm, which revealed that the ryanodine receptor is the potential target of 7o . The density functional theory (DFT) calculation results revealed the amide bridge, the benzene ring of anthraniloyl moiety and pyrazole ring might play an important role in the insecticidal activity through hydrophobic interactions and π-π conjugations.