Abstract
New eco-friendly approaches were proposed for the synthesis of cis-cyclopentene-annulated heterocyclic compounds containing a tetrahydroquinoline moiety. For the first time we implemented a one-pot three-component cyclocondensation of aromatic amines (aniline, 5-aminoquinoline, o-phenylenediamine), aldehydes, and cyclopentadiene (CPD) in water and in the ionic liquid. The effect of synthesized substituted 3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolines on the reproduction of house fly imago and on the initial stage of offspring ontogeny was evaluated in comparison with the effect of natural insect hormone using biological screening (Musca domestica). The most probable factors of stabilization of prepared compounds 7–10 in the active site of the Heliothis virescens receptor were identified using AutoDock 4.2, AutoDock Vina, and GOLD Suite molecular docking software. According to the results of three scoring functions, 4-(3-chlorophenyl)-8-fluoro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline forms the most stable complex with the chosen receptor. The results of bioassays and molecular docking indicate that these compounds may be considered as potential ecdysone agonists.
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Acknowledgements
The authors thank the Russian Foundation for Basic Research (Grant No. 20-03-00649) for financial support. A part of the studies was carried out in accordance with the Federal Program FMRS-2022-0081.
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Savchenko, R.G., Limantseva, R.M., Benkovskaya, G.V. et al. Eco-friendly synthesis of substituted tetrahydroquinolines as potential ecdysone receptor agonists. Chem. Pap. 77, 5495–5506 (2023). https://doi.org/10.1007/s11696-023-02880-7
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DOI: https://doi.org/10.1007/s11696-023-02880-7