N-Aryl 2,6-Dimethoxybiphenylalanine Analogues as VLA-4 Antagonists
A series of N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4. N-phenyl and N-heteroaryl derivatives with hydrogen bond acceptors in the meta position demonstrated low nanomolar activity against VLA-4. A series of N-arylated ph...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2002-03, Vol.12 (5), p.729-731 |
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| container_issue | 5 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 12 |
| creator | Doherty, George A Kamenecka, Theodore McCauley, Ermenegilda Van Riper, Gail Mumford, Richard A Tong, Sharon Hagmann, William K |
| description | A series of
N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4.
N-phenyl and
N-heteroaryl derivatives with hydrogen bond acceptors in the
meta position demonstrated low nanomolar activity against VLA-4.
A series of
N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4. Both aryl and heteroaryl derivatives were examined. Substitution of the
meta position of either the aryl or heteroaryl ring with hydrogen bond acceptors provided the most potent compounds in this series. |
| doi_str_mv | 10.1016/S0960-894X(02)00009-4 |
| format | Article |
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N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4.
N-phenyl and
N-heteroaryl derivatives with hydrogen bond acceptors in the
meta position demonstrated low nanomolar activity against VLA-4.
A series of
N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4. Both aryl and heteroaryl derivatives were examined. Substitution of the
meta position of either the aryl or heteroaryl ring with hydrogen bond acceptors provided the most potent compounds in this series.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(02)00009-4</identifier><identifier>PMID: 11858990</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Biological and medical sciences ; Immunomodulators ; Integrin alpha4beta1 ; Integrins - antagonists & inhibitors ; Medical sciences ; Molecular Structure ; Pharmacology. Drug treatments ; Phenylalanine - analogs & derivatives ; Phenylalanine - chemical synthesis ; Phenylalanine - pharmacology ; Receptors, Lymphocyte Homing - antagonists & inhibitors ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2002-03, Vol.12 (5), p.729-731</ispartof><rights>2002 Elsevier Science Ltd</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-5e4c6a369cda3209f42a0492991646793b584adb73b659c8935162134b76fa583</citedby><cites>FETCH-LOGICAL-c391t-5e4c6a369cda3209f42a0492991646793b584adb73b659c8935162134b76fa583</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X02000094$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13491829$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11858990$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Doherty, George A</creatorcontrib><creatorcontrib>Kamenecka, Theodore</creatorcontrib><creatorcontrib>McCauley, Ermenegilda</creatorcontrib><creatorcontrib>Van Riper, Gail</creatorcontrib><creatorcontrib>Mumford, Richard A</creatorcontrib><creatorcontrib>Tong, Sharon</creatorcontrib><creatorcontrib>Hagmann, William K</creatorcontrib><title>N-Aryl 2,6-Dimethoxybiphenylalanine Analogues as VLA-4 Antagonists</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of
N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4.
N-phenyl and
N-heteroaryl derivatives with hydrogen bond acceptors in the
meta position demonstrated low nanomolar activity against VLA-4.
A series of
N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4. Both aryl and heteroaryl derivatives were examined. Substitution of the
meta position of either the aryl or heteroaryl ring with hydrogen bond acceptors provided the most potent compounds in this series.</description><subject>Biological and medical sciences</subject><subject>Immunomodulators</subject><subject>Integrin alpha4beta1</subject><subject>Integrins - antagonists & inhibitors</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenylalanine - analogs & derivatives</subject><subject>Phenylalanine - chemical synthesis</subject><subject>Phenylalanine - pharmacology</subject><subject>Receptors, Lymphocyte Homing - antagonists & inhibitors</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMlKBDEQhoMoOi6PoMxFUTCapZLunGTchUEPLngL6XRaIz3dY9IjztubWdCjdSkovqr6-RDapeSEEipPH4mSBOcKXg8JOyKpFIYV1KMgAXMgYhX1fpENtBnjByEUCMA62qA0F7lSpIfO7_EgTOs-O5b40o9c995-Tws_fnfNtDa1aXzj-oPG1O3bxMW-if2X4QBDGnXmrW187OI2WqtMHd3Osm-h5-urp4tbPHy4ubsYDLHlinZYOLDScKlsaTgjqgJmCCimFJUgM8ULkYMpi4wXUiibKy6oZJRDkcnKiJxvoYPF3XFoP1OYTo98tK5OIV07iTqjkIkMWALFArShjTG4So-DH5kw1ZTomTw9l6dnZjRhei5PQ9rbWz6YFCNX_m0tbSVgfwmYaE1dBdNYH_84DormTCXubMG5pOPLu6Cj9a6xrvTB2U6Xrf8nyg-hk4kV</recordid><startdate>20020311</startdate><enddate>20020311</enddate><creator>Doherty, George A</creator><creator>Kamenecka, Theodore</creator><creator>McCauley, Ermenegilda</creator><creator>Van Riper, Gail</creator><creator>Mumford, Richard A</creator><creator>Tong, Sharon</creator><creator>Hagmann, William K</creator><general>Elsevier Ltd</general><general>Elsevier</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>20020311</creationdate><title>N-Aryl 2,6-Dimethoxybiphenylalanine Analogues as VLA-4 Antagonists</title><author>Doherty, George A ; Kamenecka, Theodore ; McCauley, Ermenegilda ; Van Riper, Gail ; Mumford, Richard A ; Tong, Sharon ; Hagmann, William K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-5e4c6a369cda3209f42a0492991646793b584adb73b659c8935162134b76fa583</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Biological and medical sciences</topic><topic>Immunomodulators</topic><topic>Integrin alpha4beta1</topic><topic>Integrins - antagonists & inhibitors</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenylalanine - analogs & derivatives</topic><topic>Phenylalanine - chemical synthesis</topic><topic>Phenylalanine - pharmacology</topic><topic>Receptors, Lymphocyte Homing - antagonists & inhibitors</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Doherty, George A</creatorcontrib><creatorcontrib>Kamenecka, Theodore</creatorcontrib><creatorcontrib>McCauley, Ermenegilda</creatorcontrib><creatorcontrib>Van Riper, Gail</creatorcontrib><creatorcontrib>Mumford, Richard A</creatorcontrib><creatorcontrib>Tong, Sharon</creatorcontrib><creatorcontrib>Hagmann, William K</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Doherty, George A</au><au>Kamenecka, Theodore</au><au>McCauley, Ermenegilda</au><au>Van Riper, Gail</au><au>Mumford, Richard A</au><au>Tong, Sharon</au><au>Hagmann, William K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Aryl 2,6-Dimethoxybiphenylalanine Analogues as VLA-4 Antagonists</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2002-03-11</date><risdate>2002</risdate><volume>12</volume><issue>5</issue><spage>729</spage><epage>731</epage><pages>729-731</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of
N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4.
N-phenyl and
N-heteroaryl derivatives with hydrogen bond acceptors in the
meta position demonstrated low nanomolar activity against VLA-4.
A series of
N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4. Both aryl and heteroaryl derivatives were examined. Substitution of the
meta position of either the aryl or heteroaryl ring with hydrogen bond acceptors provided the most potent compounds in this series.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>11858990</pmid><doi>10.1016/S0960-894X(02)00009-4</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Bioorganic & medicinal chemistry letters, 2002-03, Vol.12 (5), p.729-731 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Biological and medical sciences Immunomodulators Integrin alpha4beta1 Integrins - antagonists & inhibitors Medical sciences Molecular Structure Pharmacology. Drug treatments Phenylalanine - analogs & derivatives Phenylalanine - chemical synthesis Phenylalanine - pharmacology Receptors, Lymphocyte Homing - antagonists & inhibitors Structure-Activity Relationship |
| title | N-Aryl 2,6-Dimethoxybiphenylalanine Analogues as VLA-4 Antagonists |
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