ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Eco-friendly synthesis of substituted tetrahydroquinolines as potential ecdysone receptor agonists

Rimma G. Savchenko, Regina M. Limantseva, Galina V. Benkovskaya, Veronica R. Khairullina, and Oleg S. Mozgovoj

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences, Ufa, Russian Federation

E-mail: ecdysona@gmail.com

Received: 14 November 2022  Accepted: 18 May 2023

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.

Keywords: Tetrahydroquinoline; Ecdysone agonists; Eco-friendly approaches; Povarov reaction

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02880-7

Chemical Papers 77 (9) 5495–5506 (2023)