Design and synthesis of novel pyridinium nitrate-bearing substituted anilines via one-pot tandem reactions

FGLamide allatostatins (ASTs) are regarded as possible insecticide candidates, although their lack of in vivo effects, rapid degradation, poor water solubility, and high production costs preclude their practical use in pest control. In contrast to previous research, the C-terminal tripeptide (FGLa) was selected as the lead compound in this study. Five nonpeptide AST analogues (2-amino-1-[3-oxo-3-(substituted-anilino)propyl]pyridinium nitrate derivatives) were designed on the basis of the structure-activity relationship and docking results of FGLa. All of the nonpeptide analogues (S1-S5) were more potent against juvenile-hormone (JH) biosynthesis than the lead compound. They significantly inhibited the biosynthesis of JH in vivo following injection. A pest-control application demonstrated that S1 and S3 have larvicidal effects following oral administration (the IC values were 0.020 and 0.0016 mg/g, respectively). The good oral toxicities and excellent water solubilities of S1 and S3 suggest that they have considerable potential as insecticides for pest management.

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Design and synthesis of novel pyridinium nitrate-bearing substituted anilines via one-pot tandem reactions

Cited by 3 publications

References 14 publications

Pyridines and Their Benzo Derivatives: Reactivity at the Ring

Pyridines and Their Benzo Derivatives: Reactivity at the Ring

Mechanistic investigation of molecular geometry, intermolecular interactions and spectroscopic properties of pyridinium nitrate

Structure-Based Discovery of Nonpeptide Allatostatin Analogues for Pest Control

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