Serotonin 5-HT4 Receptor Agonistic Activity of the Optical Isomers of (±)-4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide
The enantiomers, (R)-(-)-1 and (S)-(+)-1, of (±)-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide [(±)-1] were prepared from optically active benzyl 4-acetylamino-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxylate[(R)-(+)-6, (S)-(-)-6], respe...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1998/06/15, Vol.46(6), pp.1039-1043 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | KAKIGAMI, Takuji USUI, Toshinao IKAMI, Takao TSUKAMOTO, Katsura MIWA, Yoshihisa TAGA, Tooru KATAOKA, Tadashi |
| description | The enantiomers, (R)-(-)-1 and (S)-(+)-1, of (±)-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide [(±)-1] were prepared from optically active benzyl 4-acetylamino-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxylate[(R)-(+)-6, (S)-(-)-6], respectively. The requisite (R)-(+)-6 and (S)-(-)-6 were prepared by large-scale preparative HPLC on chiral stationary phases (CSPs). The absolute configuration of (S)-(+)-1 was determined by single crystal X-ray analysis. The serotonin 5-HT4 receptor agonistic activity of (S)-(-)-1 hemifumarate (SK-951) which was hemifumarate of (S)-(+)-1 was about twice that of the other enantiomer (R)-(+)-1 hemifumarate which was hemifumarate of (R)-(-)-1. |
| doi_str_mv | 10.1248/cpb.46.1039 |
| format | Article |
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The requisite (R)-(+)-6 and (S)-(-)-6 were prepared by large-scale preparative HPLC on chiral stationary phases (CSPs). The absolute configuration of (S)-(+)-1 was determined by single crystal X-ray analysis. The serotonin 5-HT4 receptor agonistic activity of (S)-(-)-1 hemifumarate (SK-951) which was hemifumarate of (S)-(+)-1 was about twice that of the other enantiomer (R)-(+)-1 hemifumarate which was hemifumarate of (R)-(-)-1.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.46.1039</identifier><identifier>PMID: 9658578</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>5-HT4 receptor agonistic activity ; absolute configuration ; Animals ; Biological and medical sciences ; Crystallography, X-Ray ; enantiomer ; Esophagus - drug effects ; Esophagus - metabolism ; large-scale preparative HPLC ; Medical sciences ; Muscle Relaxation - drug effects ; Muscle, Smooth - drug effects ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; optical resolution ; Pharmacology. Drug treatments ; Rats ; Receptors, Serotonin - drug effects ; Receptors, Serotonin - metabolism ; Receptors, Serotonin, 5-HT4 ; Serotonin Receptor Agonists - chemical synthesis ; Serotonin Receptor Agonists - pharmacology ; Serotoninergic system ; SK-951 ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1998/06/15, Vol.46(6), pp.1039-1043</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1998 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1998</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c565t-f976fb38735814e756b8c89726dd83d868f2eca05ae805ef20494c288b873df73</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,1877,27905,27906</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2332598$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9658578$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KAKIGAMI, Takuji</creatorcontrib><creatorcontrib>USUI, Toshinao</creatorcontrib><creatorcontrib>IKAMI, Takao</creatorcontrib><creatorcontrib>TSUKAMOTO, Katsura</creatorcontrib><creatorcontrib>MIWA, Yoshihisa</creatorcontrib><creatorcontrib>TAGA, Tooru</creatorcontrib><creatorcontrib>KATAOKA, Tadashi</creatorcontrib><title>Serotonin 5-HT4 Receptor Agonistic Activity of the Optical Isomers of (±)-4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The enantiomers, (R)-(-)-1 and (S)-(+)-1, of (±)-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide [(±)-1] were prepared from optically active benzyl 4-acetylamino-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxylate[(R)-(+)-6, (S)-(-)-6], respectively. The requisite (R)-(+)-6 and (S)-(-)-6 were prepared by large-scale preparative HPLC on chiral stationary phases (CSPs). The absolute configuration of (S)-(+)-1 was determined by single crystal X-ray analysis. The serotonin 5-HT4 receptor agonistic activity of (S)-(-)-1 hemifumarate (SK-951) which was hemifumarate of (S)-(+)-1 was about twice that of the other enantiomer (R)-(+)-1 hemifumarate which was hemifumarate of (R)-(-)-1.</description><subject>5-HT4 receptor agonistic activity</subject><subject>absolute configuration</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Crystallography, X-Ray</subject><subject>enantiomer</subject><subject>Esophagus - drug effects</subject><subject>Esophagus - metabolism</subject><subject>large-scale preparative HPLC</subject><subject>Medical sciences</subject><subject>Muscle Relaxation - drug effects</subject><subject>Muscle, Smooth - drug effects</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>optical resolution</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Receptors, Serotonin - drug effects</subject><subject>Receptors, Serotonin - metabolism</subject><subject>Receptors, Serotonin, 5-HT4</subject><subject>Serotonin Receptor Agonists - chemical synthesis</subject><subject>Serotonin Receptor Agonists - pharmacology</subject><subject>Serotoninergic system</subject><subject>SK-951</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkctu1DAUhiMEKkNhxRopEgi1Ag-OHTv2clQurVRRCcpqNIoc56TjURIH21M1fStW7HkynM5okNjYPuf_zkX-k-RlhucZycUHPVTznM8zTOWjZJbRvECMEPo4mWGMJSKU06fJM-83GBOGC3qUHEnOBCvELPn9HZwNtjd9ytD5dZ5-Aw1DsC5d3MSsD0anCx3MrQljaps0rCG9GmJWtemFtx04P6VP_vw6RTladKa36CtaEnSSIXWvKqNH3dolndM5XlkdVI8YGttTCOuxXcW3XrfWWUTepxTVZj3WU4C6B72C_t4uq1WzdbGuQFq5yt6pztTwPHnSqNbDi_19nPz4_On67BxdXn25OFtcIs04C6iRBW8qKgrKRJZDwXgltJAF4XUtaC24aAhohZkCgRk0BOcy10SIKpbUTUGPk7e7voOzP7fgQ9kZr6FtVQ9268tCSkmEFBF8_R-4sVvXx93KLOeYZjR6Fal3O0o7672Dphyc6ZQbywyXk5llNLPMeTmZGelX-57bqoP6wO7di_qbva58NKSJv6SNP2CEUsIeVvu4wzY-qBs46MpFH1uYRmaSiWks3x3T9H_yWrkSevoXn9u9ww</recordid><startdate>19980601</startdate><enddate>19980601</enddate><creator>KAKIGAMI, Takuji</creator><creator>USUI, Toshinao</creator><creator>IKAMI, Takao</creator><creator>TSUKAMOTO, Katsura</creator><creator>MIWA, Yoshihisa</creator><creator>TAGA, Tooru</creator><creator>KATAOKA, Tadashi</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>19980601</creationdate><title>Serotonin 5-HT4 Receptor Agonistic Activity of the Optical Isomers of (±)-4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide</title><author>KAKIGAMI, Takuji ; USUI, Toshinao ; IKAMI, Takao ; TSUKAMOTO, Katsura ; MIWA, Yoshihisa ; TAGA, Tooru ; KATAOKA, Tadashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c565t-f976fb38735814e756b8c89726dd83d868f2eca05ae805ef20494c288b873df73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>5-HT4 receptor agonistic activity</topic><topic>absolute configuration</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Crystallography, X-Ray</topic><topic>enantiomer</topic><topic>Esophagus - drug effects</topic><topic>Esophagus - metabolism</topic><topic>large-scale preparative HPLC</topic><topic>Medical sciences</topic><topic>Muscle Relaxation - drug effects</topic><topic>Muscle, Smooth - drug effects</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>optical resolution</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Receptors, Serotonin - drug effects</topic><topic>Receptors, Serotonin - metabolism</topic><topic>Receptors, Serotonin, 5-HT4</topic><topic>Serotonin Receptor Agonists - chemical synthesis</topic><topic>Serotonin Receptor Agonists - pharmacology</topic><topic>Serotoninergic system</topic><topic>SK-951</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KAKIGAMI, Takuji</creatorcontrib><creatorcontrib>USUI, Toshinao</creatorcontrib><creatorcontrib>IKAMI, Takao</creatorcontrib><creatorcontrib>TSUKAMOTO, Katsura</creatorcontrib><creatorcontrib>MIWA, Yoshihisa</creatorcontrib><creatorcontrib>TAGA, Tooru</creatorcontrib><creatorcontrib>KATAOKA, Tadashi</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KAKIGAMI, Takuji</au><au>USUI, Toshinao</au><au>IKAMI, Takao</au><au>TSUKAMOTO, Katsura</au><au>MIWA, Yoshihisa</au><au>TAGA, Tooru</au><au>KATAOKA, Tadashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Serotonin 5-HT4 Receptor Agonistic Activity of the Optical Isomers of (±)-4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1998-06-01</date><risdate>1998</risdate><volume>46</volume><issue>6</issue><spage>1039</spage><epage>1043</epage><pages>1039-1043</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>The enantiomers, (R)-(-)-1 and (S)-(+)-1, of (±)-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide [(±)-1] were prepared from optically active benzyl 4-acetylamino-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxylate[(R)-(+)-6, (S)-(-)-6], respectively. The requisite (R)-(+)-6 and (S)-(-)-6 were prepared by large-scale preparative HPLC on chiral stationary phases (CSPs). The absolute configuration of (S)-(+)-1 was determined by single crystal X-ray analysis. The serotonin 5-HT4 receptor agonistic activity of (S)-(-)-1 hemifumarate (SK-951) which was hemifumarate of (S)-(+)-1 was about twice that of the other enantiomer (R)-(+)-1 hemifumarate which was hemifumarate of (R)-(-)-1.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>9658578</pmid><doi>10.1248/cpb.46.1039</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1998/06/15, Vol.46(6), pp.1039-1043 |
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| language | eng |
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| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | 5-HT4 receptor agonistic activity absolute configuration Animals Biological and medical sciences Crystallography, X-Ray enantiomer Esophagus - drug effects Esophagus - metabolism large-scale preparative HPLC Medical sciences Muscle Relaxation - drug effects Muscle, Smooth - drug effects Neuropharmacology Neurotransmitters. Neurotransmission. Receptors optical resolution Pharmacology. Drug treatments Rats Receptors, Serotonin - drug effects Receptors, Serotonin - metabolism Receptors, Serotonin, 5-HT4 Serotonin Receptor Agonists - chemical synthesis Serotonin Receptor Agonists - pharmacology Serotoninergic system SK-951 Stereoisomerism Structure-Activity Relationship |
| title | Serotonin 5-HT4 Receptor Agonistic Activity of the Optical Isomers of (±)-4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide |
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