title: Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase.
abstract: A series of 2-(substituted) phenyl and 2-indolyl quinoline derivatives (10a-l) was synthesized by an efficient microwave-assisted, trifluoroacetic acid-catalyzed, solvent-free method. Evaluation of the inhibitory activity led to the identification of two quinoline inhibitors of cholesterol esterase. 2-(1H-Indol-3-yl)-6-nitro-4-phenylquinoline (10l; IC50=1.98μM) was characterized as a mixed-type inhibitor with a pronounced competitive binding mode.
authors.affiliation: Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, Ciudad Autónoma de Buenos Aires C1113AAB, Argentina.
authors.forename: Gisela C
authors.initials: GC
authors.lastname: Muscia
authors.affiliation: Pharmaceutical Institute, University of Bonn, An der Immenburg 4, Bonn D-53115, Germany.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Hautmann
authors.affiliation: Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, Ciudad Autónoma de Buenos Aires C1113AAB, Argentina.
authors.forename: Graciela Y
authors.initials: GY
authors.lastname: Buldain
authors.affiliation: Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, Ciudad Autónoma de Buenos Aires C1113AAB, Argentina.
authors.forename: Silvia E
authors.initials: SE
authors.lastname: Asís
authors.affiliation: Pharmaceutical Institute, University of Bonn, An der Immenburg 4, Bonn D-53115, Germany. Electronic address: guetschow@uni-bonn.de.
authors.forename: Michael
authors.initials: M
authors.lastname: Gütschow
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D002417:Cattle; D057056:Cysteine Proteases / Q000737:chemistry / Q000378:metabolism; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D007700:Kinetics; D008872:Microwaves; D011485:Protein Binding; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D002787:Sterol Esterase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship; D013552:Swine
chemical_list: D004791:Enzyme Inhibitors; D011804:Quinolines; C037219:quinoline; D002787:Sterol Esterase; D057056:Cysteine Proteases
keywords: Cholesterol esterase; Friedländer reaction; Mixed-type inhibition; Quinolines