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- W2887133358 abstract "Tetrahydroquinolines (THQs) are a class of non-steroidal ecdysone agonists that specifically bind to mosquito ecdysone receptors (EcR). The THQ scaffold contains two chiral centers at the C-2 and C-4 positions, resulting in four stereoisomers. We have previously shown that the (2R,4S)-isomers are the most biologically active; however, the lack of a practical synthetic method for these isomers has hampered further structure-activity studies.In this study, a chiral phosphoric acid-catalyzed Povarov reaction was employed to develop a facile asymmetric synthesis of THQs with a (2R,4S)-configuration, which allowed the preparation of a 40-compound library of enantiopure THQs. Evaluation of their binding affinity against Aedes albopictus EcR, followed by quantitative structure-activity relationship (QSAR) analyses, uncovered the physicochemical properties of THQs that are important for the ligand-receptor interaction. The most potent THQ derivative was twofold more active than the molting hormone, 20-hydroxyecdysone.The QSAR results provide valuable information for the rational design of novel mosquito-specific ecdysone agonists. © 2018 Society of Chemical Industry." @default.
- W2887133358 created "2018-08-22" @default.
- W2887133358 creator A5001846908 @default.
- W2887133358 creator A5020225564 @default.
- W2887133358 creator A5085001876 @default.
- W2887133358 date "2018-10-09" @default.
- W2887133358 modified "2023-10-16" @default.
- W2887133358 title "Asymmetric synthesis of tetrahydroquinoline‐type ecdysone agonists and QSAR for their binding affinity against <scp> <i>Aedes albopictus</i> </scp> ecdysone receptors" @default.
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- W2887133358 doi "https://doi.org/10.1002/ps.5160" @default.
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