{"doi":"10.1002/ardp.201300321","title":"Synthesis and Biological Screening of Novel Indolalkyl Arenes Targeting the Serotonine Transporter","abstract":"<jats:sec><jats:label/><jats:p>A series of functionalized indolylalkylarenes <jats:bold>3</jats:bold>–<jats:bold>16</jats:bold>(<jats:bold>a</jats:bold> and <jats:bold>b</jats:bold>) were synthesized and their affinities for the serotonin transporter were investigated <jats:italic>in vitro</jats:italic>. Compounds <jats:bold>3</jats:bold>–<jats:bold>12</jats:bold>(<jats:bold>a</jats:bold> and <jats:bold>b</jats:bold>) were obtained by nucleophilic substitution of 3‐(1<jats:italic>H</jats:italic>‐indol‐3‐yl)propyl‐4‐methylbenzenesulfonates <jats:bold>2</jats:bold>(<jats:bold>a</jats:bold> and <jats:bold>b</jats:bold>) with a series of azaheterocycles. Compounds <jats:bold>14</jats:bold>–<jats:bold>16</jats:bold>(<jats:bold>a</jats:bold> and <jats:bold>b</jats:bold>) were prepared in a two‐step sequence by reaction of 3‐(1<jats:italic>H</jats:italic>‐indol‐3‐yl)‐2‐methylpropanal with substituted 1,2‐phenylenediamines. Compounds <jats:bold>3b</jats:bold>, <jats:bold>4b</jats:bold>, and <jats:bold>5b</jats:bold> showed good binding affinities (<jats:italic>K</jats:italic><jats:sub>i</jats:sub> = 33.0, 48.0, and 17 nM, respectively). The other synthesized compounds showed moderate or no affinity in the binding studies.</jats:p></jats:sec>","journal":"Archiv der Pharmazie","year":2014,"id":43847,"datarank":0.36400666886662153,"base_score":2.0794415416798357,"endowment":2.0794415416798357,"self_citation_contribution":0.31191623125197543,"citation_network_contribution":0.052090437614646115,"self_endowment_contribution":0.31191623125197543,"citer_contribution":0.052090437614646115,"corpus_percentile":null,"corpus_rank":null,"citation_count":7,"citer_count":3,"citers_with_citation_signal":3,"citers_with_endowment":3,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":207494,"name":"Hernán Pessoa‐Mahana","orcid":null,"position":1,"is_corresponding":false},{"id":207495,"name":"Patricio Iturriaga‐Vásquez","orcid":null,"position":2,"is_corresponding":false},{"id":207496,"name":"Carlos David Pessoa‐Mahana","orcid":null,"position":3,"is_corresponding":false},{"id":207497,"name":"Gonzalo Recabarren‐Gajardo","orcid":null,"position":4,"is_corresponding":false},{"id":207498,"name":"Claudio Méndez‐Rojas","orcid":null,"position":5,"is_corresponding":false},{"id":207493,"name":"Claudia Ojeda‐Gómez","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":2.0794415416798357,"endowment":2.0794415416798357,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"24339227","pmcid":null,"openalex_id":"https://openalex.org/W1933643218","authors":[],"funders":[],"total_grants":0,"fwci":0.1705,"citation_percentile":0.54539388,"influential_citations":0,"citation_trend":[{"year":2016,"count":1},{"year":2018,"count":2},{"year":2020,"count":3},{"year":2024,"count":1}],"oa_status":"green","license":"other-oa","oa_locations":[{"url":"http://americanae.aecid.es/americanae/es/registros/registro.do?tipoRegistro=MTD&idBib=3302429","host_type":"repository"},{"url":"http://americanae.aecid.es/americanae/es/registros/registro.do?tipoRegistro=MTD&idBib=3302429","host_type":"repository"},{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fardp.201300321","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/ardp.201300321","host_type":"publisher"},{"url":"https://doi.org/10.1002/ardp.201300321","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/24339227","host_type":"repository"},{"url":"http://hdl.handle.net/10533/127428","host_type":"repository"},{"url":"http://repositorio.uchile.cl/handle/2250/121958","host_type":"repository"}],"fields_of_study":["Synthesis and Biological Evaluation","Synthesis of Indole Derivatives","Nicotinic Acetylcholine Receptors Study","Chemistry","Medicine","HEK293 Cells","Humans","Indoles","Molecular Structure","Serotonin Plasma Membrane Transport Proteins","Selective Serotonin Reuptake Inhibitors","Structure-Activity Relationship","Transfection"],"mesh_terms":["Humans","Indoles","Structure-Activity Relationship","Transfection","Molecular Structure","Selective Serotonin Reuptake Inhibitors","Serotonin Plasma Membrane Transport Proteins","HEK293 Cells"],"keywords":["Chemistry","Affinities","Binding affinities","Stereochemistry","Transporter","Serotonin transporter","In vitro","Nucleophile","Chemical synthesis","Nucleophilic substitution","Sequence (biology)","Biological activity","Combinatorial chemistry","Serotonin","Organic chemistry","Biochemistry","Receptor","Benzimidazole","Indole","Serotonine Transporter"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-15T03:50:46.209251Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}