title: Synthesis, insecticidal activities and SAR of novel phthalamides targeting calcium channel.
abstract: In order to find novel and environmental friendly insecticides targeting the ryanodine receptor, three series of novel phthalamides containing heptafluoroisopropyl group, low fluorine atoms group and non-fluorine group were designed and synthesized. 35 novel structures of three series were obtained. Insecticidal activities of title compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of title compounds showed moderate to high activities at the tested concentration. The structure-activity relationship (SAR) was discussed in detail. During synthesizing title compounds B8, C7, D1, D9 and D12, their corresponding positional isomers (B8', C7', D1', D9' and D12') were afforded, and their structures were confirmed by 2D NMR. The calcium-imaging technique was also applied to investigate the effects of compounds B2, B10, C4 and C5 on the intracellular calcium ion concentration ([Ca(2+)]i), which indicated that they released stored calcium ions from endoplasmic reticulum, which denoted that some compounds are potential modulators of the insect ryanodine receptor (RyR).
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Youwei
authors.initials: Y
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Li
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Jingbo
authors.initials: J
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Yingying
authors.initials: Y
authors.lastname: Wan
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Wei
authors.initials: W
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Lixia
authors.initials: L
authors.lastname: Xiong
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Na
authors.initials: N
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Haibin
authors.initials: H
authors.lastname: Song
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Zhengming
authors.initials: Z
authors.lastname: Li
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D000818:Animals; D002118:Calcium / Q000378:metabolism; D015220:Calcium Channels / Q000737:chemistry* / Q000378:metabolism; D018360:Crystallography, X-Ray; D004721:Endoplasmic Reticulum / Q000378:metabolism; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D007814:Larva / Q000187:drug effects; D007915:Lepidoptera / Q000254:growth & development; D008968:Molecular Conformation; D009036:Moths; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D015220:Calcium Channels; D007306:Insecticides; D002118:Calcium
keywords: Calcium channel; Fluorine; Insecticidal activity; Phthalamides