Inhibition of adhesion molecule expression by N-alkylthiopyridine-benzo[ b]thiophene-2-carboxamides
The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by 3-alkoxybenzo[ b]thiophene-2-carboxamides. This property is shared by several N-alkylthiopyridine substituted imides. Combining structural elements of these two diverse series lead to a new class of small mo...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 1996-04, Vol.4 (4), p.557-562 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Boschelli, Diane H. Connor, David T. Lesch, Mark E. Schrier, Denis J. |
| description | The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by 3-alkoxybenzo[
b]thiophene-2-carboxamides. This property is shared by several
N-alkylthiopyridine substituted imides. Combining structural elements of these two diverse series lead to a new class of small molecule inhibitors of adhesion molecule expression.
The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by
N-alkylthiopyridinebenzo[
b]thiophene-2-carboxamides. In ELISA assays compound 14 had IC
50s of 5.7 and 8.4 μM for the inhibition of ICAM-1 and E-selectin expression, respectively. |
| doi_str_mv | 10.1016/0968-0896(96)00046-6 |
| format | Article |
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b]thiophene-2-carboxamides. This property is shared by several
N-alkylthiopyridine substituted imides. Combining structural elements of these two diverse series lead to a new class of small molecule inhibitors of adhesion molecule expression.
The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by
N-alkylthiopyridinebenzo[
b]thiophene-2-carboxamides. In ELISA assays compound 14 had IC
50s of 5.7 and 8.4 μM for the inhibition of ICAM-1 and E-selectin expression, respectively.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/0968-0896(96)00046-6</identifier><identifier>PMID: 8735844</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - pharmacology ; Cell Adhesion - drug effects ; Cells, Cultured ; E-Selectin - biosynthesis ; E-Selectin - drug effects ; Endothelium, Vascular - cytology ; Endothelium, Vascular - drug effects ; Enzyme-Linked Immunosorbent Assay ; Humans ; Intercellular Adhesion Molecule-1 - biosynthesis ; Intercellular Adhesion Molecule-1 - drug effects ; Pyridines - chemical synthesis ; Pyridines - pharmacology ; Structure-Activity Relationship ; Thiophenes - chemical synthesis ; Thiophenes - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 1996-04, Vol.4 (4), p.557-562</ispartof><rights>1996</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c423t-33ac3b833f128cb49359d1b7c5dea90e4f35ed75c5fcbc7cf395d6d3c1b859863</citedby><cites>FETCH-LOGICAL-c423t-33ac3b833f128cb49359d1b7c5dea90e4f35ed75c5fcbc7cf395d6d3c1b859863</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0968089696000466$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8735844$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Boschelli, Diane H.</creatorcontrib><creatorcontrib>Connor, David T.</creatorcontrib><creatorcontrib>Lesch, Mark E.</creatorcontrib><creatorcontrib>Schrier, Denis J.</creatorcontrib><title>Inhibition of adhesion molecule expression by N-alkylthiopyridine-benzo[ b]thiophene-2-carboxamides</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by 3-alkoxybenzo[
b]thiophene-2-carboxamides. This property is shared by several
N-alkylthiopyridine substituted imides. Combining structural elements of these two diverse series lead to a new class of small molecule inhibitors of adhesion molecule expression.
The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by
N-alkylthiopyridinebenzo[
b]thiophene-2-carboxamides. In ELISA assays compound 14 had IC
50s of 5.7 and 8.4 μM for the inhibition of ICAM-1 and E-selectin expression, respectively.</description><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Cell Adhesion - drug effects</subject><subject>Cells, Cultured</subject><subject>E-Selectin - biosynthesis</subject><subject>E-Selectin - drug effects</subject><subject>Endothelium, Vascular - cytology</subject><subject>Endothelium, Vascular - drug effects</subject><subject>Enzyme-Linked Immunosorbent Assay</subject><subject>Humans</subject><subject>Intercellular Adhesion Molecule-1 - biosynthesis</subject><subject>Intercellular Adhesion Molecule-1 - drug effects</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Thiophenes - chemical synthesis</subject><subject>Thiophenes - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9P3DAQxa0KRBfoNyhSTqgcAnbsOPalEkL9g4TgUk6osuzxRGuaxFs7W7H99CS7K45IlsZ68-aN_SPkM6OXjDJ5RbVUJVVaftHyglIqZCk_kAUTUpSca3ZAFm-Wj-Q45-fJVAnNjsiRanithFgQuB2WwYUxxKGIbWH9EvN872OHsO6wwJdVwrzV3Ka4L233Z9ONyxBXmxR8GLB0OPyPT4X7vVWXOElVCTa5-GL74DGfksPWdhk_7esJefz-7dfNz_Lu4cftzfVdCaLi4_RmC9wpzltWKXBC81p75hqoPVpNUbS8Rt_UULfgoIGW69pLz4E5VWsl-Qk53-WuUvy7xjyaPmTArrMDxnU2jaqEalg1GcXOCCnmnLA1qxR6mzaGUTOzNTM4M4Mz09myNXP-2T5_7Xr0b0N7mFP_666P0yf_BUwmQ8AB0IeEMBofw_sLXgHrtYrz</recordid><startdate>19960401</startdate><enddate>19960401</enddate><creator>Boschelli, Diane H.</creator><creator>Connor, David T.</creator><creator>Lesch, Mark E.</creator><creator>Schrier, Denis J.</creator><general>Elsevier Ltd</general><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>19960401</creationdate><title>Inhibition of adhesion molecule expression by N-alkylthiopyridine-benzo[ b]thiophene-2-carboxamides</title><author>Boschelli, Diane H. ; Connor, David T. ; Lesch, Mark E. ; Schrier, Denis J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c423t-33ac3b833f128cb49359d1b7c5dea90e4f35ed75c5fcbc7cf395d6d3c1b859863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Cell Adhesion - drug effects</topic><topic>Cells, Cultured</topic><topic>E-Selectin - biosynthesis</topic><topic>E-Selectin - drug effects</topic><topic>Endothelium, Vascular - cytology</topic><topic>Endothelium, Vascular - drug effects</topic><topic>Enzyme-Linked Immunosorbent Assay</topic><topic>Humans</topic><topic>Intercellular Adhesion Molecule-1 - biosynthesis</topic><topic>Intercellular Adhesion Molecule-1 - drug effects</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Thiophenes - chemical synthesis</topic><topic>Thiophenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Boschelli, Diane H.</creatorcontrib><creatorcontrib>Connor, David T.</creatorcontrib><creatorcontrib>Lesch, Mark E.</creatorcontrib><creatorcontrib>Schrier, Denis J.</creatorcontrib><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</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Boschelli, Diane H.</au><au>Connor, David T.</au><au>Lesch, Mark E.</au><au>Schrier, Denis J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibition of adhesion molecule expression by N-alkylthiopyridine-benzo[ b]thiophene-2-carboxamides</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>1996-04-01</date><risdate>1996</risdate><volume>4</volume><issue>4</issue><spage>557</spage><epage>562</epage><pages>557-562</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by 3-alkoxybenzo[
b]thiophene-2-carboxamides. This property is shared by several
N-alkylthiopyridine substituted imides. Combining structural elements of these two diverse series lead to a new class of small molecule inhibitors of adhesion molecule expression.
The surface levels of ICAM-1 and E-selectin on activated endothelial cells can be reduced by
N-alkylthiopyridinebenzo[
b]thiophene-2-carboxamides. In ELISA assays compound 14 had IC
50s of 5.7 and 8.4 μM for the inhibition of ICAM-1 and E-selectin expression, respectively.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>8735844</pmid><doi>10.1016/0968-0896(96)00046-6</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 1996-04, Vol.4 (4), p.557-562 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_78248712 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - pharmacology Cell Adhesion - drug effects Cells, Cultured E-Selectin - biosynthesis E-Selectin - drug effects Endothelium, Vascular - cytology Endothelium, Vascular - drug effects Enzyme-Linked Immunosorbent Assay Humans Intercellular Adhesion Molecule-1 - biosynthesis Intercellular Adhesion Molecule-1 - drug effects Pyridines - chemical synthesis Pyridines - pharmacology Structure-Activity Relationship Thiophenes - chemical synthesis Thiophenes - pharmacology |
| title | Inhibition of adhesion molecule expression by N-alkylthiopyridine-benzo[ b]thiophene-2-carboxamides |
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