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Synthesis and Biological Evaluation of Novel Compounds within a Class of 3-Aminochroman Derivatives with Dual 5-HT1A Receptor and Serotonin Transporter Affinity
Compounds containing a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran and a 3-alkylindole moiety linked through a common basic nitrogen were prepared and evaluated for 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonist activity in vitro. 26a was found to be the...
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| Published in: | Journal of medicinal chemistry 2006-07, Vol.49 (15), p.4785-4789 |
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| Main Authors: | , , , , , , , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| container_end_page | 4789 |
| container_issue | 15 |
| container_start_page | 4785 |
| container_title | Journal of medicinal chemistry |
| container_volume | 49 |
| creator | Hatzenbuhler, Nicole T Evrard, Deborah A Harrison, Boyd L Huryn, Donna Inghrim, Jennifer Kraml, Christina Mattes, James F Mewshaw, Richard E Zhou, Dahui Hornby, Geoffrey Lin, Qian Smith, Deborah L Sullivan, Kelly M Schechter, Lee E Beyer, Chad E Andree, Terrance H |
| description | Compounds containing a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran and a 3-alkylindole moiety linked through a common basic nitrogen were prepared and evaluated for 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonist activity in vitro. 26a was found to be the most potent and selective compound in this series and was shown to possess neurochemical activity in vivo by producing acute and rapid increases in 5-HT in the rat frontal cortex. |
| doi_str_mv | 10.1021/jm060218h |
| format | article |
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Neurotransmission. Receptors ; Pharmacology. Drug treatments ; Radioligand Assay ; Rats ; Serotonin - biosynthesis ; Serotonin 5-HT1 Receptor Agonists ; Serotonin 5-HT1 Receptor Antagonists ; Serotonin Plasma Membrane Transport Proteins - metabolism ; Serotonin Uptake Inhibitors - chemical synthesis ; Serotonin Uptake Inhibitors - chemistry ; Serotonin Uptake Inhibitors - pharmacology ; Serotoninergic system ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2006-07, Vol.49 (15), p.4785-4789</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18001571$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16854086$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hatzenbuhler, Nicole T</creatorcontrib><creatorcontrib>Evrard, Deborah A</creatorcontrib><creatorcontrib>Harrison, Boyd L</creatorcontrib><creatorcontrib>Huryn, Donna</creatorcontrib><creatorcontrib>Inghrim, Jennifer</creatorcontrib><creatorcontrib>Kraml, Christina</creatorcontrib><creatorcontrib>Mattes, James F</creatorcontrib><creatorcontrib>Mewshaw, Richard E</creatorcontrib><creatorcontrib>Zhou, Dahui</creatorcontrib><creatorcontrib>Hornby, Geoffrey</creatorcontrib><creatorcontrib>Lin, Qian</creatorcontrib><creatorcontrib>Smith, Deborah L</creatorcontrib><creatorcontrib>Sullivan, Kelly M</creatorcontrib><creatorcontrib>Schechter, Lee E</creatorcontrib><creatorcontrib>Beyer, Chad E</creatorcontrib><creatorcontrib>Andree, Terrance H</creatorcontrib><title>Synthesis and Biological Evaluation of Novel Compounds within a Class of 3-Aminochroman Derivatives with Dual 5-HT1A Receptor and Serotonin Transporter Affinity</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Compounds containing a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran and a 3-alkylindole moiety linked through a common basic nitrogen were prepared and evaluated for 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonist activity in vitro. 26a was found to be the most potent and selective compound in this series and was shown to possess neurochemical activity in vivo by producing acute and rapid increases in 5-HT in the rat frontal cortex.</description><subject>Animals</subject><subject>Antidepressive Agents - chemical synthesis</subject><subject>Antidepressive Agents - chemistry</subject><subject>Antidepressive Agents - pharmacology</subject><subject>Benzopyrans - chemical synthesis</subject><subject>Benzopyrans - chemistry</subject><subject>Benzopyrans - pharmacology</subject><subject>Biological and medical sciences</subject><subject>CHO Cells</subject><subject>Chromans - chemical synthesis</subject><subject>Chromans - chemistry</subject><subject>Chromans - pharmacology</subject><subject>Cricetinae</subject><subject>Cricetulus</subject><subject>Frontal Lobe - drug effects</subject><subject>Frontal Lobe - metabolism</subject><subject>Humans</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Medical sciences</subject><subject>Microdialysis</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pharmacology. Drug treatments</subject><subject>Radioligand Assay</subject><subject>Rats</subject><subject>Serotonin - biosynthesis</subject><subject>Serotonin 5-HT1 Receptor Agonists</subject><subject>Serotonin 5-HT1 Receptor Antagonists</subject><subject>Serotonin Plasma Membrane Transport Proteins - metabolism</subject><subject>Serotonin Uptake Inhibitors - chemical synthesis</subject><subject>Serotonin Uptake Inhibitors - chemistry</subject><subject>Serotonin Uptake Inhibitors - pharmacology</subject><subject>Serotoninergic system</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNpN0s2O0zAQB3ALgdiycOAFkC9wC9hx7LjH0v1CWmBFA-JmTRObuiR2sJ2yfRseFS8tC6c5-Dd_a0aD0HNKXlNS0jfbgYhc5eYBmlFekqKSpHqIZoSUZVGKkp2gJzFuCSGMluwxOqFC8opIMUO_VnuXNjraiMF1-K31vf9mW-jx-Q76CZL1DnuDP_id7vHSD6OfXBfxT5s21mHAyx5ivBOsWAzW-XYT_AAOn-lgd7l9pw8Yn005lBdXDV3gT7rVY_Lhz58rHXzyLqc1AVwcfUg64IUx1tm0f4oeGeijfnasp-jzxXmzvCquP16-Wy6uC2CkTkXX1ZWoNJvnwUQNfN5yzmVFqOaMUgYgjZG1FgTWTEvWtpzNTSekWBvTEVaxU_TqkDsG_2PSManBxlb3PTjtp6gy5ZWkMsMXRzitB92pMdgBwl793WkGL48AYl6kyUO1Nv5zkhDKa5pdcXA2Jn17_w7huxI1q7lqblaqYe-_XjRfbtR_udBGtfVTcHkfihJ1dwPq_gbYb2RjoWY</recordid><startdate>20060727</startdate><enddate>20060727</enddate><creator>Hatzenbuhler, Nicole T</creator><creator>Evrard, Deborah A</creator><creator>Harrison, Boyd L</creator><creator>Huryn, Donna</creator><creator>Inghrim, Jennifer</creator><creator>Kraml, Christina</creator><creator>Mattes, James F</creator><creator>Mewshaw, Richard E</creator><creator>Zhou, Dahui</creator><creator>Hornby, Geoffrey</creator><creator>Lin, Qian</creator><creator>Smith, Deborah L</creator><creator>Sullivan, Kelly M</creator><creator>Schechter, Lee E</creator><creator>Beyer, Chad E</creator><creator>Andree, Terrance H</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20060727</creationdate><title>Synthesis and Biological Evaluation of Novel Compounds within a Class of 3-Aminochroman Derivatives with Dual 5-HT1A Receptor and Serotonin Transporter Affinity</title><author>Hatzenbuhler, Nicole T ; Evrard, Deborah A ; Harrison, Boyd L ; Huryn, Donna ; Inghrim, Jennifer ; Kraml, Christina ; Mattes, James F ; Mewshaw, Richard E ; Zhou, Dahui ; Hornby, Geoffrey ; Lin, Qian ; Smith, Deborah L ; Sullivan, Kelly M ; Schechter, Lee E ; Beyer, Chad E ; Andree, Terrance H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a307t-dd7464e3985467a59c5558401e53113aa8ff87e60ab3e83cc539fd686bffd0343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Antidepressive Agents - chemical synthesis</topic><topic>Antidepressive Agents - chemistry</topic><topic>Antidepressive Agents - pharmacology</topic><topic>Benzopyrans - chemical synthesis</topic><topic>Benzopyrans - chemistry</topic><topic>Benzopyrans - pharmacology</topic><topic>Biological and medical sciences</topic><topic>CHO Cells</topic><topic>Chromans - chemical synthesis</topic><topic>Chromans - chemistry</topic><topic>Chromans - pharmacology</topic><topic>Cricetinae</topic><topic>Cricetulus</topic><topic>Frontal Lobe - drug effects</topic><topic>Frontal Lobe - metabolism</topic><topic>Humans</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Medical sciences</topic><topic>Microdialysis</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Pharmacology. Drug treatments</topic><topic>Radioligand Assay</topic><topic>Rats</topic><topic>Serotonin - biosynthesis</topic><topic>Serotonin 5-HT1 Receptor Agonists</topic><topic>Serotonin 5-HT1 Receptor Antagonists</topic><topic>Serotonin Plasma Membrane Transport Proteins - metabolism</topic><topic>Serotonin Uptake Inhibitors - chemical synthesis</topic><topic>Serotonin Uptake Inhibitors - chemistry</topic><topic>Serotonin Uptake Inhibitors - pharmacology</topic><topic>Serotoninergic system</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hatzenbuhler, Nicole T</creatorcontrib><creatorcontrib>Evrard, Deborah A</creatorcontrib><creatorcontrib>Harrison, Boyd L</creatorcontrib><creatorcontrib>Huryn, Donna</creatorcontrib><creatorcontrib>Inghrim, Jennifer</creatorcontrib><creatorcontrib>Kraml, Christina</creatorcontrib><creatorcontrib>Mattes, James F</creatorcontrib><creatorcontrib>Mewshaw, Richard E</creatorcontrib><creatorcontrib>Zhou, Dahui</creatorcontrib><creatorcontrib>Hornby, Geoffrey</creatorcontrib><creatorcontrib>Lin, Qian</creatorcontrib><creatorcontrib>Smith, Deborah L</creatorcontrib><creatorcontrib>Sullivan, Kelly M</creatorcontrib><creatorcontrib>Schechter, Lee E</creatorcontrib><creatorcontrib>Beyer, Chad E</creatorcontrib><creatorcontrib>Andree, Terrance H</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hatzenbuhler, Nicole T</au><au>Evrard, Deborah A</au><au>Harrison, Boyd L</au><au>Huryn, Donna</au><au>Inghrim, Jennifer</au><au>Kraml, Christina</au><au>Mattes, James F</au><au>Mewshaw, Richard E</au><au>Zhou, Dahui</au><au>Hornby, Geoffrey</au><au>Lin, Qian</au><au>Smith, Deborah L</au><au>Sullivan, Kelly M</au><au>Schechter, Lee E</au><au>Beyer, Chad E</au><au>Andree, Terrance H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Evaluation of Novel Compounds within a Class of 3-Aminochroman Derivatives with Dual 5-HT1A Receptor and Serotonin Transporter Affinity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2006-07-27</date><risdate>2006</risdate><volume>49</volume><issue>15</issue><spage>4785</spage><epage>4789</epage><pages>4785-4789</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Compounds containing a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran and a 3-alkylindole moiety linked through a common basic nitrogen were prepared and evaluated for 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonist activity in vitro. 26a was found to be the most potent and selective compound in this series and was shown to possess neurochemical activity in vivo by producing acute and rapid increases in 5-HT in the rat frontal cortex.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16854086</pmid><doi>10.1021/jm060218h</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2006-07, Vol.49 (15), p.4785-4789 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Animals Antidepressive Agents - chemical synthesis Antidepressive Agents - chemistry Antidepressive Agents - pharmacology Benzopyrans - chemical synthesis Benzopyrans - chemistry Benzopyrans - pharmacology Biological and medical sciences CHO Cells Chromans - chemical synthesis Chromans - chemistry Chromans - pharmacology Cricetinae Cricetulus Frontal Lobe - drug effects Frontal Lobe - metabolism Humans Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Medical sciences Microdialysis Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pharmacology. Drug treatments Radioligand Assay Rats Serotonin - biosynthesis Serotonin 5-HT1 Receptor Agonists Serotonin 5-HT1 Receptor Antagonists Serotonin Plasma Membrane Transport Proteins - metabolism Serotonin Uptake Inhibitors - chemical synthesis Serotonin Uptake Inhibitors - chemistry Serotonin Uptake Inhibitors - pharmacology Serotoninergic system Stereoisomerism Structure-Activity Relationship |
| title | Synthesis and Biological Evaluation of Novel Compounds within a Class of 3-Aminochroman Derivatives with Dual 5-HT1A Receptor and Serotonin Transporter Affinity |
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