Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity
The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol. In addition, two achiral pyranenamines 19 and 26 were also synthesized. When evaluated by intravenous a...
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| Veröffentlicht in: | Journal of medicinal chemistry 1991-01, Vol.34 (1), p.392-397 |
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| container_end_page | 397 |
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| container_issue | 1 |
| container_start_page | 392 |
| container_title | Journal of medicinal chemistry |
| container_volume | 34 |
| creator | Gluchowski, Charles Bischoff, Trudy E Garst, Michael E Kaplan, Lester J Dietrich, Steven W Aswad, Angelika S Gaffney, Mary A Aoki, K. Roger Garcia, Carlos Wheeler, Larry A |
| description | The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol. In addition, two achiral pyranenamines 19 and 26 were also synthesized. When evaluated by intravenous and topical routes in the rat passive ocular anaphylaxis (POA) assay, (SS)- and meso-2 as well as achiral compounds 19 and 26 were found to be more potent antiallergic agents than (RR)-2. |
| doi_str_mv | 10.1021/jm00105a060 |
| format | Article |
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When evaluated by intravenous and topical routes in the rat passive ocular anaphylaxis (POA) assay, (SS)- and meso-2 as well as achiral compounds 19 and 26 were found to be more potent antiallergic agents than (RR)-2.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00105a060</identifier><identifier>PMID: 1671418</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anaphylaxis - drug therapy ; Aniline Compounds - chemical synthesis ; Aniline Compounds - therapeutic use ; Animals ; Chemistry ; Exact sciences and technology ; Eye Diseases - drug therapy ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Histamine H1 Antagonists - chemical synthesis ; Indicators and Reagents ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Pyrones - chemical synthesis ; Pyrones - therapeutic use ; Rats ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1991-01, Vol.34 (1), p.392-397</ispartof><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a384t-f653727d1f7367d53e05b16fd80895a9ca8b49f91fc4edeb1439aa4a0ee46b4e3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00105a060$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00105a060$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,4012,27063,27910,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19614716$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1671418$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gluchowski, Charles</creatorcontrib><creatorcontrib>Bischoff, Trudy E</creatorcontrib><creatorcontrib>Garst, Michael E</creatorcontrib><creatorcontrib>Kaplan, Lester J</creatorcontrib><creatorcontrib>Dietrich, Steven W</creatorcontrib><creatorcontrib>Aswad, Angelika S</creatorcontrib><creatorcontrib>Gaffney, Mary A</creatorcontrib><creatorcontrib>Aoki, K. Roger</creatorcontrib><creatorcontrib>Garcia, Carlos</creatorcontrib><creatorcontrib>Wheeler, Larry A</creatorcontrib><title>Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol. In addition, two achiral pyranenamines 19 and 26 were also synthesized. When evaluated by intravenous and topical routes in the rat passive ocular anaphylaxis (POA) assay, (SS)- and meso-2 as well as achiral compounds 19 and 26 were found to be more potent antiallergic agents than (RR)-2.</description><subject>Anaphylaxis - drug therapy</subject><subject>Aniline Compounds - chemical synthesis</subject><subject>Aniline Compounds - therapeutic use</subject><subject>Animals</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Eye Diseases - drug therapy</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Histamine H1 Antagonists - chemical synthesis</subject><subject>Indicators and Reagents</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyrones - chemical synthesis</subject><subject>Pyrones - therapeutic use</subject><subject>Rats</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtv1DAURi0EKtPCijVSNsACpVw_4iTLUspDVFDUYW3dODcdD3lMbacw_x6jjCgLNral79xP14exZxxOOQj-ZjsAcCgQNDxgK14IyFUF6iFbAQiRCy3kY3YcwhYAJBfyiB1xXXLFqxW7vd6PcUPBhWzqMrtxHvsMxzbDw3u39zjSiIMbKWvJuzuM7o7CaXY1RRpjhjfpDNlPFzdZnHbOpqHJzj361BMd9j35G2dTYZpzcf-EPeqwD_T0cJ-w7-8v1ucf88uvHz6dn13mKCsV804XshRly7tS6rItJEHRcN21FVR1gbXFqlF1V_POKmqp4UrWiAqBSOlGkTxhL5fenZ9uZwrRDC5Y6vv0nWkOJhmSGoRM4OsFtH4KwVNndt4N6PeGg_kj2PwjONHPD7VzM1B7zy5GU_7ikGNIKrpkz7pwj9Waq5LrxOUL50KkX39z9D-MLmVZmPXVtVm__VLwd98-mzrxrxYebTDbafZjkvffDX8DiwOgZw</recordid><startdate>19910101</startdate><enddate>19910101</enddate><creator>Gluchowski, Charles</creator><creator>Bischoff, Trudy E</creator><creator>Garst, Michael E</creator><creator>Kaplan, Lester J</creator><creator>Dietrich, Steven W</creator><creator>Aswad, Angelika S</creator><creator>Gaffney, Mary A</creator><creator>Aoki, K. Roger</creator><creator>Garcia, Carlos</creator><creator>Wheeler, Larry A</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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19910101</creationdate><title>Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity</title><author>Gluchowski, Charles ; Bischoff, Trudy E ; Garst, Michael E ; Kaplan, Lester J ; Dietrich, Steven W ; Aswad, Angelika S ; Gaffney, Mary A ; Aoki, K. Roger ; Garcia, Carlos ; Wheeler, Larry A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a384t-f653727d1f7367d53e05b16fd80895a9ca8b49f91fc4edeb1439aa4a0ee46b4e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Anaphylaxis - drug therapy</topic><topic>Aniline Compounds - chemical synthesis</topic><topic>Aniline Compounds - therapeutic use</topic><topic>Animals</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Eye Diseases - drug therapy</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Histamine H1 Antagonists - chemical synthesis</topic><topic>Indicators and Reagents</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyrones - chemical synthesis</topic><topic>Pyrones - therapeutic use</topic><topic>Rats</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gluchowski, Charles</creatorcontrib><creatorcontrib>Bischoff, Trudy E</creatorcontrib><creatorcontrib>Garst, Michael E</creatorcontrib><creatorcontrib>Kaplan, Lester J</creatorcontrib><creatorcontrib>Dietrich, Steven W</creatorcontrib><creatorcontrib>Aswad, Angelika S</creatorcontrib><creatorcontrib>Gaffney, Mary A</creatorcontrib><creatorcontrib>Aoki, K. Roger</creatorcontrib><creatorcontrib>Garcia, Carlos</creatorcontrib><creatorcontrib>Wheeler, Larry A</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>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>Gluchowski, Charles</au><au>Bischoff, Trudy E</au><au>Garst, Michael E</au><au>Kaplan, Lester J</au><au>Dietrich, Steven W</au><au>Aswad, Angelika S</au><au>Gaffney, Mary A</au><au>Aoki, K. Roger</au><au>Garcia, Carlos</au><au>Wheeler, Larry A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1991-01-01</date><risdate>1991</risdate><volume>34</volume><issue>1</issue><spage>392</spage><epage>397</epage><pages>392-397</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol. In addition, two achiral pyranenamines 19 and 26 were also synthesized. When evaluated by intravenous and topical routes in the rat passive ocular anaphylaxis (POA) assay, (SS)- and meso-2 as well as achiral compounds 19 and 26 were found to be more potent antiallergic agents than (RR)-2.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>1671418</pmid><doi>10.1021/jm00105a060</doi><tpages>6</tpages></addata></record> |
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| subjects | Anaphylaxis - drug therapy Aniline Compounds - chemical synthesis Aniline Compounds - therapeutic use Animals Chemistry Exact sciences and technology Eye Diseases - drug therapy Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Histamine H1 Antagonists - chemical synthesis Indicators and Reagents Molecular Structure Organic chemistry Preparations and properties Pyrones - chemical synthesis Pyrones - therapeutic use Rats Stereoisomerism Structure-Activity Relationship |
| title | Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity |
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