title: Synthesis and in vitro Evaluation of Novel Indole-Based Sigma Receptors Ligands.
abstract: To investigate the molecular features involved in sigma (σ) receptors binding, a series of compounds based on indole scaffolds were synthesized and their chemical structures were confirmed by (1) H-NMR, IR, and elemental analysis. Their affinity toward σ(1)  and σ(2)  receptor subtypes was evaluated. 1-{[4-(2-phenylethyl)piperazin-1-yl]methyl}-3-methyl-1H-indole 3b had a high affinity to σ(1)  receptors, while three compounds, 1-{3-[4-(substitutedphenyl)piperazin-1-yl]propyl}-1H-indole derivatives 4a-c had shown high affinity and selectivity for σ(2)  receptors. Cytotoxicity of the compounds was demonstrated on cancer cell lines from liver (HUH7), breast (MCF7), and colon (HCT-116) cancer cell lines. Compound 1c (3-{[4-(3,4-dichlorobenzyl)piperazin-1-yl]methyl}-1H-indole) showed significant cell growth inhibitory activity on the selected cancer cell lines.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yeditepe University, 34755 Kayisdagi, Istanbul, Turkey. myarim@yeditepe.edu.tr
authors.forename: Mine
authors.initials: M
authors.lastname: Yarim
authors.forename: Meric
authors.initials: M
authors.lastname: Koksal
authors.forename: Dirk
authors.initials: D
authors.lastname: Schepmann
authors.forename: Bernard
authors.initials: B
authors.lastname: Wünsch
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008024:Ligands; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D017480:Receptors, sigma / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: C569931:3-((4-(3,4-dichlorobenzyl)piperazin-1-yl)methyl)-1H-indole; D000970:Antineoplastic Agents; D007211:Indoles; D008024:Ligands; D010879:Piperazines; D017480:Receptors, sigma; C030374:indole