Design and synthesis of novel insecticides based on the serotonergic ligand 1-[(4-aminophenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazine (PAPP).

Mingyi Cai, Zhong Li, Feng Fan, Qingchun Huang, Xusheng Shao, Gonghua Song

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, P.O. Box 544, 130 Meilong Road, Shanghai 200237, People's Republic of China.

Journal of agricultural and food chemistry 2010 Mar 10

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1-[(4-Aminophenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazine (PAPP) is a 5-HT(1A) agonist and was reported to display high affinity for serotonin (5-HT) receptor from the parasitic nematode Haemonchus contortus . The present investigation explored the possibility of using PAPP as a lead compound of new insecticides with novel mode of action. On the basis of the PAPP scaffold, a series of 1-arylmethyl-4-[(trifluoromethyl)pyridin-2-yl]piperazine derivatives were designed, synthesized, and evaluated for biological activities against the armyworm Pseudaletia separata (Walker). Bioassays showed that most of the target compounds displayed certain growth-inhibiting activities or larvicidal activities against armyworm. The quantitative structure-activity relationship (QSAR) for growth-inhibiting activities was also analyzed and established.

Citation

Mingyi Cai, Zhong Li, Feng Fan, Qingchun Huang, Xusheng Shao, Gonghua Song. Design and synthesis of novel insecticides based on the serotonergic ligand 1-[(4-aminophenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazine (PAPP). Journal of agricultural and food chemistry. 2010 Mar 10;58(5):2624-9