Synthesis of Quinoline and Dihydroquinoline Embelin Derivatives as Cardioprotective Agents

• DOI: 10.1021/acs.jnatprod.2c00924
• Publication Date: 2023-02-07T20:54:25Z
• Authors: Pedro Martín-Acosta; Irene Cuadrado; Laura González-Co...; Roberto Pestano; Sonsoles Hortelano; Beatriz de las Heras; Ana Estévez-Braun
• Keywords: Quinoline

A set of new dihydroquinoline embelin derivatives was obtained from the reaction natural benzoquinone (1) with anilines and aromatic aldehydes in presence AgOTf. The synthesis these compounds involves formation a Knoevenagel adduct, followed by nucleophilic addition aniline subsequent electrocyclic ring closure. scope regarding determined. Quinoline were also corresponding dihydroquinolines under oxidation DDQ. cardioprotective activity synthesized screened using doxorubicin-induced cardiotoxicity model H9c2 cardiomyocytes. Some structure-activity relationships outlined, best activities achieved quinoline-embelin having 4-nitrophenyl group attached at pyridine ring. results indicated that 4i, 6a, 6d, 6k, 6m could have potential as agents, they attenuated DOX-induced effect acting on oxidative stress apoptosis.