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Sun C.,Shanghai Normal University | Chen Y.,Shanghai Normal University | Liu T.,Shanghai Normal University | Wu Y.,Shanghai Normal University | And 3 more authors.
Chinese Journal of Chemistry | Year: 2012

A novel series of cis-nitenpyram analogues (2a-2p) were designed and prepared by introducing the 1,4-dihydropyridine, with their cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most compounds exhibited good insecticidal activities at 20 mg/L against Aphis medicagini, and analogues 2a and 2d afforded the best activity, and both of them had 100% mortality at 4 mg/L. In addition, molecular docking studies were also performed to model the ligand-receptor complexes, and the results explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides. Copyright © 2012 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Sun C.,Shanghai Normal University | Zhu J.,Shanghai Normal University | Wang H.,Shanghai Normal University | Jin J.,Shanghai Normal University | And 2 more authors.
European Journal of Medicinal Chemistry | Year: 2011

A new series of 1,5-disubstituted 1,3,5-hexahydrotriazine-2-N-nitroimines (4a-4x) were designed and synthesized as novel chiral neonicotinoid analogues. The single-crystal structure of 4n was further determined by X-ray diffraction, and its S configuration was confirmed. Preliminary bioassay showed that compound 4e, 4k, 4u, 4v exhibited excellent insecticidal activities at 100 mg/L, while 4k had >90% mortality at 10 mg/L, which suggested it could be used as a lead for future development. Modeling the inhibitor-nAChR complexes by molecular docking studies explained the structure-activity relationships observed in vitro, and revealed an intriguing molecular binding mode at the active site of nAChR, which raised the possibility that these analogues may arbitrate their insecticidal activity through a mechanism other than imidacloprid. Source


Sun C.-W.,Shanghai Normal University | Wang H.-F.,Shanghai Normal University | Zhu J.,Shanghai Normal University | Yang D.-R.,Shanghai Normal University | And 2 more authors.
Journal of Heterocyclic Chemistry | Year: 2011

Figure represented. A series of novel neonicotinoids analogs were designed by modifying the pharmacophore of imidacloprid to 1,3,5-hexahydrotriazine conjugated to nitroimine (ïNNO2) and introducing the phenyl or arylmethyl at the 5-position, and their insecticidal activities were evaluated. Introducing a heterocyclic methyl at 5-position increased the insecticidal activities, whereas other phenyl, phenylmethyl or phenylethyl substituents were unfavorable to activities. Molecular docking study was also performed to clarify the interactions of the most potent analog 1-((6-chloropyridin-3-yl)methyl)-5- (3-pyridylmethyl)-1,3,5-hexahydrotriazine-2-(N-nitro) imine (7s) with the target nicotinic acetylcholine receptor, which explained the structure-activity relationships observed in vitro, and revealed further possibilities for insecticide development. © 2011 HeteroCorporation. Source


Sun C.,Shanghai Normal University | Xu X.,Shanghai Normal University | Xu Y.,Branch of National Pesticide R and uth Center | Yan D.,Shanghai Normal University | And 2 more authors.
Journal of Agricultural and Food Chemistry | Year: 2011

To make further researches on the structure-activity relationships (SARs) of our previous synthesized neonicotinoid compounds, a new series of nitenpyam analogues with flexible ester arm were synthesized. Preliminary bioassays indicated that all of our newly designed nitenpyam analogues exhibited good insecticidal activity at 100 mg/L, while analogues 4c and 4d afforded the best in vitro activity, and both of them had 100% mortality at 20 mg/L. The SAR studies suggested that their insecticidal potency was dual-controlled by the length of the ester arm and the size of the ester group. In addition, the molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode, which explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these novel nitenpyam analogues. © 2011 American Chemical Society. Source


Chuanwen S.,Shanghai Normal University | Dingrong Y.,Shanghai Normal University | Jiahua X.,Branch of National Pesticide R and uth Center | Haifeng W.,Shanghai Normal University | And 2 more authors.
Journal of Agricultural and Food Chemistry | Year: 2010

Two series of new nitromethylene neonicotinoid analogues (2a-2h and 3a-3h) were designed and prepared, with the cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most analogues exhibited excellent insectlcidal activities at 500 mg/L, and analogues with optical activity (2c-2g) were highly potent at 100 mg/L, while compound 2d had >90% mortality at 20 mg/L, which suggested that it could be used as a lead for future insecticides development. Modeling the ligand-receptor complexes by molecular docking study explained the structureactivity relationships observed in vitro and revealed an intriguing molecular binding mode at the active site of the nAChR model, thereby possibly providing some useful information for future receptor structure-based designs of novel insecticidal compounds. © 2010 American Chemical Society. Source

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