title: Synthesis and biological screening of novel indolalkyl arenes targeting the serotonine transporter.
abstract: A series of functionalized indolylalkylarenes 3-16(a and b) were synthesized and their affinities for the serotonin transporter were investigated in vitro. Compounds 3-12(a and b) were obtained by nucleophilic substitution of 3-(1H-indol-3-yl)propyl-4-methylbenzenesulfonates 2(a and b) with a series of azaheterocycles. Compounds 14-16(a and b) were prepared in a two-step sequence by reaction of 3-(1H-indol-3-yl)-2-methylpropanal with substituted 1,2-phenylenediamines. Compounds 3b, 4b, and 5b showed good binding affinities (K(i) = 33.0, 48.0, and 17 nM, respectively). The other synthesized compounds showed moderate or no affinity in the binding studies.
authors: Faculty of Chemical and Pharmaceutical Sciences, Department of Organic and Physical Chemistry, University of Chile, Santiago, Chile.
authors: Claudia
authors: C
authors: Ojeda-Gómez
authors: Hernán
authors: H
authors: Pessoa-Mahana
authors: Patricio
authors: P
authors: Iturriaga-Vásquez
authors: Carlos David
authors: CD
authors: Pessoa-Mahana
authors: Gonzalo
authors: G
authors: Recabarren-Gajardo
authors: Claudio
authors: C
authors: Méndez-Rojas
mesh_terms: D057809:HEK293 Cells; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000378:metabolism* / Q000494:pharmacology; D015394:Molecular Structure; D050486:Serotonin Plasma Membrane Transport Proteins / Q000187:drug effects / Q000235:genetics / Q000378:metabolism*; D017367:Selective Serotonin Reuptake Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014162:Transfection
chemical_list: D007211:Indoles; D050486:Serotonin Plasma Membrane Transport Proteins; D017367:Selective Serotonin Reuptake Inhibitors
keywords: Benzimidazole; Indole; Serotonine transporter