Synthesis of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine as insecticidal agents. Issue 2 (1st February 2021)

• Record Type: Journal Article
• Authors: Che, Zhi-Ping; Yang, Jin-Ming; Zhang, Song; Sun, Di; Tian, Yue-E; Liu, Sheng-Ming; Lin, Xiao-Min; Jiang, Jia; Chen, Gen-Qiang
• Is Part Of: Journal of Asian natural products research. Volume 23:Issue 2(2021)
• Page Start: 163
• Page End: 175
• Publication Date: 2021-02-01
• Subjects: Cinchonidine -- cinchonine -- quinine analogues -- acyloxy -- insecticidal activity; Materia medica -- Asia -- Periodicals; Pharmacognosy -- Asia -- Periodicals; Medicinal plants -- Asia -- Periodicals; Medicine, Oriental -- Asia -- Periodicals; 615.321095
• DOI: 10.1080/10286020.2020.1729136
• Languages: English
• ISSNs: 1028-6020

Abstract

Abstract: Endeavor to discover biorational natural products-based insecticides, two series (27) of novel 9 R/S -acyloxy derivatives of cinchonidine and cinchonine were prepared and assessed for their insecticidal activity against Mythimna separata in vivo by the leaf-dipping method at 1 mg/mL. Among all the compounds, especially derivatives 6l and 6o exhibited the best insecticidal activity with final mortality rates of 75.0% and 71.4%, respectively. Overall, a free 9-hydroxyl group is not a prerequisite for insecticidal activity and C9-substitution is well tolerated; the configuration of C8/9 position is important for insecticidal activity, and 9 S -configuration is optimal; 6'-OCH3 moiety is not necessary, removal of it is also acceptable.