Enantioselectivity in Cardioprotection induced by (S)- (−)-2,2-Dimethyl-N-(4′-acetamido-benzyl)-4-spiromorpholone-chromane
This work aimed to determine the enantioselectivity in cardioprotection induced by the racemic mixture of the “archetype” 1a of a new class of spirocyclic-benzopyran derivatives. The racemate was resolved by HPLC and the absolute configuration was accomplished by a combined strategy based on single-...
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| Veröffentlicht in: | Journal of medicinal chemistry 2009-03, Vol.52 (5), p.1477-1480 |
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| container_title | Journal of medicinal chemistry |
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| creator | Rapposelli, Simona Calderone, Vincenzo Cirilli, Roberto Digiacomo, Maria Faggi, Cristina La Torre, Francesco Manganaro, Mariaelisa Martelli, Alma Testai, Lara |
| description | This work aimed to determine the enantioselectivity in cardioprotection induced by the racemic mixture of the “archetype” 1a of a new class of spirocyclic-benzopyran derivatives. The racemate was resolved by HPLC and the absolute configuration was accomplished by a combined strategy based on single-crystal X-ray diffraction and circular dichroism methods. The (S)-(−)-1a enantiomer, evaluated for its anti-ischemic activity, showed significant cardioprotective effects, whereas the (R)-(+)-1a enantiomer was completely lacking in anti-ischemic effects. |
| doi_str_mv | 10.1021/jm801459f |
| format | Article |
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The racemate was resolved by HPLC and the absolute configuration was accomplished by a combined strategy based on single-crystal X-ray diffraction and circular dichroism methods. The (S)-(−)-1a enantiomer, evaluated for its anti-ischemic activity, showed significant cardioprotective effects, whereas the (R)-(+)-1a enantiomer was completely lacking in anti-ischemic effects.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm801459f</identifier><identifier>PMID: 19215088</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Columbus, OH: American Chemical Society</publisher><subject>Animals ; Benzopyrans - chemical synthesis ; Benzopyrans - chemistry ; Benzopyrans - therapeutic use ; Biological and medical sciences ; Cardiotonic Agents - chemical synthesis ; Cardiotonic Agents - chemistry ; Cardiotonic Agents - therapeutic use ; Cardiovascular system ; Chromatography, High Pressure Liquid ; Circular Dichroism ; Crystallography, X-Ray ; In Vitro Techniques ; Medical sciences ; Miscellaneous ; Models, Molecular ; Molecular Conformation ; Myocardial Ischemia - drug therapy ; Myocardial Ischemia - pathology ; Myocardial Ischemia - physiopathology ; Myocardial Reperfusion ; Pharmacology. Drug treatments ; Rats ; Spiro Compounds - chemical synthesis ; Spiro Compounds - chemistry ; Spiro Compounds - therapeutic use ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2009-03, Vol.52 (5), p.1477-1480</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a344t-d7c6cb518e7ade0a443bc379c9185ccf16b413c522295c60529d282205b457ca3</citedby><cites>FETCH-LOGICAL-a344t-d7c6cb518e7ade0a443bc379c9185ccf16b413c522295c60529d282205b457ca3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm801459f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm801459f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21262370$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19215088$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rapposelli, Simona</creatorcontrib><creatorcontrib>Calderone, Vincenzo</creatorcontrib><creatorcontrib>Cirilli, Roberto</creatorcontrib><creatorcontrib>Digiacomo, Maria</creatorcontrib><creatorcontrib>Faggi, Cristina</creatorcontrib><creatorcontrib>La Torre, Francesco</creatorcontrib><creatorcontrib>Manganaro, Mariaelisa</creatorcontrib><creatorcontrib>Martelli, Alma</creatorcontrib><creatorcontrib>Testai, Lara</creatorcontrib><title>Enantioselectivity in Cardioprotection induced by (S)- (−)-2,2-Dimethyl-N-(4′-acetamido-benzyl)-4-spiromorpholone-chromane</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>This work aimed to determine the enantioselectivity in cardioprotection induced by the racemic mixture of the “archetype” 1a of a new class of spirocyclic-benzopyran derivatives. The racemate was resolved by HPLC and the absolute configuration was accomplished by a combined strategy based on single-crystal X-ray diffraction and circular dichroism methods. The (S)-(−)-1a enantiomer, evaluated for its anti-ischemic activity, showed significant cardioprotective effects, whereas the (R)-(+)-1a enantiomer was completely lacking in anti-ischemic effects.</description><subject>Animals</subject><subject>Benzopyrans - chemical synthesis</subject><subject>Benzopyrans - chemistry</subject><subject>Benzopyrans - therapeutic use</subject><subject>Biological and medical sciences</subject><subject>Cardiotonic Agents - chemical synthesis</subject><subject>Cardiotonic Agents - chemistry</subject><subject>Cardiotonic Agents - therapeutic use</subject><subject>Cardiovascular system</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Circular Dichroism</subject><subject>Crystallography, X-Ray</subject><subject>In Vitro Techniques</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Myocardial Ischemia - drug therapy</subject><subject>Myocardial Ischemia - pathology</subject><subject>Myocardial Ischemia - physiopathology</subject><subject>Myocardial Reperfusion</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - therapeutic use</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkcFq3DAQhkVJaLZpD32B4kvILkSNNJLW1jFs0yYQ2kOSs5HHMqvFlraSHXAPpcee-yh9pDxJvWRJLj0N8_Pxz8w_hLzn7CNnwM83XcG4VLp5RWZcAaOyYPKAzBgDoLAEcUTepLRhjAkO4jU54hq4YkUxIz8vvfG9C8m2Fnv34Poxcz5bmVi7sI2h36nBT1o9oK2zaszmtwuazR9__1lQOAP6yXW2X48t_Urn8vHXX2rQ9qZzdaCV9T_GdkElTVsXQxfidh3a4C3F9dQab9-Sw8a0yb7b12Ny__nybnVFb759uV5d3FAjpOxpneMSK8ULm5vaMiOlqFDkGjUvFGLDl5XkAhUAaIVLpkDXUAAwVUmVoxHH5PTJdzrp-2BTX3YuoW3baYcwpDIXgktdaD2RiycSY0gp2qbcRteZOJaclbu0y-e0J_bD3nWoOlu_kPt4J-BkD5iEpm2i8ejSMwd895ycvXAGU7kJQ_RTGP8Z-A87JZQt</recordid><startdate>20090312</startdate><enddate>20090312</enddate><creator>Rapposelli, Simona</creator><creator>Calderone, Vincenzo</creator><creator>Cirilli, Roberto</creator><creator>Digiacomo, Maria</creator><creator>Faggi, Cristina</creator><creator>La Torre, Francesco</creator><creator>Manganaro, Mariaelisa</creator><creator>Martelli, Alma</creator><creator>Testai, Lara</creator><general>American Chemical Society</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>7X8</scope></search><sort><creationdate>20090312</creationdate><title>Enantioselectivity in Cardioprotection induced by (S)- (−)-2,2-Dimethyl-N-(4′-acetamido-benzyl)-4-spiromorpholone-chromane</title><author>Rapposelli, Simona ; Calderone, Vincenzo ; Cirilli, Roberto ; Digiacomo, Maria ; Faggi, Cristina ; La Torre, Francesco ; Manganaro, Mariaelisa ; Martelli, Alma ; Testai, Lara</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-d7c6cb518e7ade0a443bc379c9185ccf16b413c522295c60529d282205b457ca3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Animals</topic><topic>Benzopyrans - chemical synthesis</topic><topic>Benzopyrans - chemistry</topic><topic>Benzopyrans - therapeutic use</topic><topic>Biological and medical sciences</topic><topic>Cardiotonic Agents - chemical synthesis</topic><topic>Cardiotonic Agents - chemistry</topic><topic>Cardiotonic Agents - therapeutic use</topic><topic>Cardiovascular system</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Circular Dichroism</topic><topic>Crystallography, X-Ray</topic><topic>In Vitro Techniques</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Myocardial Ischemia - drug therapy</topic><topic>Myocardial Ischemia - pathology</topic><topic>Myocardial Ischemia - physiopathology</topic><topic>Myocardial Reperfusion</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - chemistry</topic><topic>Spiro Compounds - therapeutic use</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rapposelli, Simona</creatorcontrib><creatorcontrib>Calderone, Vincenzo</creatorcontrib><creatorcontrib>Cirilli, Roberto</creatorcontrib><creatorcontrib>Digiacomo, Maria</creatorcontrib><creatorcontrib>Faggi, Cristina</creatorcontrib><creatorcontrib>La Torre, Francesco</creatorcontrib><creatorcontrib>Manganaro, Mariaelisa</creatorcontrib><creatorcontrib>Martelli, Alma</creatorcontrib><creatorcontrib>Testai, Lara</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rapposelli, Simona</au><au>Calderone, Vincenzo</au><au>Cirilli, Roberto</au><au>Digiacomo, Maria</au><au>Faggi, Cristina</au><au>La Torre, Francesco</au><au>Manganaro, Mariaelisa</au><au>Martelli, Alma</au><au>Testai, Lara</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselectivity in Cardioprotection induced by (S)- (−)-2,2-Dimethyl-N-(4′-acetamido-benzyl)-4-spiromorpholone-chromane</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2009-03-12</date><risdate>2009</risdate><volume>52</volume><issue>5</issue><spage>1477</spage><epage>1480</epage><pages>1477-1480</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>This work aimed to determine the enantioselectivity in cardioprotection induced by the racemic mixture of the “archetype” 1a of a new class of spirocyclic-benzopyran derivatives. The racemate was resolved by HPLC and the absolute configuration was accomplished by a combined strategy based on single-crystal X-ray diffraction and circular dichroism methods. The (S)-(−)-1a enantiomer, evaluated for its anti-ischemic activity, showed significant cardioprotective effects, whereas the (R)-(+)-1a enantiomer was completely lacking in anti-ischemic effects.</abstract><cop>Columbus, OH</cop><pub>American Chemical Society</pub><pmid>19215088</pmid><doi>10.1021/jm801459f</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2009-03, Vol.52 (5), p.1477-1480 |
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| subjects | Animals Benzopyrans - chemical synthesis Benzopyrans - chemistry Benzopyrans - therapeutic use Biological and medical sciences Cardiotonic Agents - chemical synthesis Cardiotonic Agents - chemistry Cardiotonic Agents - therapeutic use Cardiovascular system Chromatography, High Pressure Liquid Circular Dichroism Crystallography, X-Ray In Vitro Techniques Medical sciences Miscellaneous Models, Molecular Molecular Conformation Myocardial Ischemia - drug therapy Myocardial Ischemia - pathology Myocardial Ischemia - physiopathology Myocardial Reperfusion Pharmacology. Drug treatments Rats Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Spiro Compounds - therapeutic use Stereoisomerism Structure-Activity Relationship |
| title | Enantioselectivity in Cardioprotection induced by (S)- (−)-2,2-Dimethyl-N-(4′-acetamido-benzyl)-4-spiromorpholone-chromane |
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