Discovery of selective phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE)
A novel series of phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE) was discovered by structural modification of tetrahydroisoquinoline derivative 1b, which was extremely weak inhibitor of TACE. ( S)-Isomer at the phosphorus atom ( 7b) displayed potent inhibition for...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2003-06, Vol.13 (12), p.2021-2024 |
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| container_end_page | 2024 |
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| container_issue | 12 |
| container_start_page | 2021 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 13 |
| creator | Sawa, Masaaki Kurokawa, Kiriko Inoue, Yoshimasa Kondo, Hirosato Yoshino, Kohichiro |
| description | A novel series of phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE) was discovered by structural modification of tetrahydroisoquinoline derivative
1b, which was extremely weak inhibitor of TACE. (
S)-Isomer at the phosphorus atom (
7b) displayed potent inhibition for TACE, while selectivity sparing MMP-1, -3, and -9.
The synthesis and biological data for a series of novel acyclic phosphonamide-based inhibitors of TACE is reported. |
| doi_str_mv | 10.1016/S0960-894X(03)00292-0 |
| format | Article |
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1b, which was extremely weak inhibitor of TACE. (
S)-Isomer at the phosphorus atom (
7b) displayed potent inhibition for TACE, while selectivity sparing MMP-1, -3, and -9.
The synthesis and biological data for a series of novel acyclic phosphonamide-based inhibitors of TACE is reported.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(03)00292-0</identifier><identifier>PMID: 12781187</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>ADAM Proteins ; ADAM17 Protein ; Amides - chemistry ; Amides - pharmacology ; Binding Sites ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Drug Design ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Isomerism ; Matrix Metalloproteinase Inhibitors ; Matrix Metalloproteinases - metabolism ; Medical sciences ; Metalloendopeptidases - antagonists & inhibitors ; Models, Molecular ; Organophosphonates - chemistry ; Organophosphonates - pharmacology ; Pharmacology. Drug treatments ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2003-06, Vol.13 (12), p.2021-2024</ispartof><rights>2003 Elsevier Science Ltd</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-8d4d747d2102cd9b19d45a0c5b7b0b5c908760065fbaa0ee110f28575b0255e03</citedby><cites>FETCH-LOGICAL-c391t-8d4d747d2102cd9b19d45a0c5b7b0b5c908760065fbaa0ee110f28575b0255e03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X03002920$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14829690$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12781187$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sawa, Masaaki</creatorcontrib><creatorcontrib>Kurokawa, Kiriko</creatorcontrib><creatorcontrib>Inoue, Yoshimasa</creatorcontrib><creatorcontrib>Kondo, Hirosato</creatorcontrib><creatorcontrib>Yoshino, Kohichiro</creatorcontrib><title>Discovery of selective phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE)</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A novel series of phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE) was discovered by structural modification of tetrahydroisoquinoline derivative
1b, which was extremely weak inhibitor of TACE. (
S)-Isomer at the phosphorus atom (
7b) displayed potent inhibition for TACE, while selectivity sparing MMP-1, -3, and -9.
The synthesis and biological data for a series of novel acyclic phosphonamide-based inhibitors of TACE is reported.</description><subject>ADAM Proteins</subject><subject>ADAM17 Protein</subject><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Drug Design</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Isomerism</subject><subject>Matrix Metalloproteinase Inhibitors</subject><subject>Matrix Metalloproteinases - metabolism</subject><subject>Medical sciences</subject><subject>Metalloendopeptidases - antagonists & inhibitors</subject><subject>Models, Molecular</subject><subject>Organophosphonates - chemistry</subject><subject>Organophosphonates - pharmacology</subject><subject>Pharmacology. 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Antiinflammatory agents</topic><topic>Drug Design</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Isomerism</topic><topic>Matrix Metalloproteinase Inhibitors</topic><topic>Matrix Metalloproteinases - metabolism</topic><topic>Medical sciences</topic><topic>Metalloendopeptidases - antagonists & inhibitors</topic><topic>Models, Molecular</topic><topic>Organophosphonates - chemistry</topic><topic>Organophosphonates - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sawa, Masaaki</creatorcontrib><creatorcontrib>Kurokawa, Kiriko</creatorcontrib><creatorcontrib>Inoue, Yoshimasa</creatorcontrib><creatorcontrib>Kondo, Hirosato</creatorcontrib><creatorcontrib>Yoshino, Kohichiro</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>Sawa, Masaaki</au><au>Kurokawa, Kiriko</au><au>Inoue, Yoshimasa</au><au>Kondo, Hirosato</au><au>Yoshino, Kohichiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of selective phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE)</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2003-06-16</date><risdate>2003</risdate><volume>13</volume><issue>12</issue><spage>2021</spage><epage>2024</epage><pages>2021-2024</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A novel series of phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE) was discovered by structural modification of tetrahydroisoquinoline derivative
1b, which was extremely weak inhibitor of TACE. (
S)-Isomer at the phosphorus atom (
7b) displayed potent inhibition for TACE, while selectivity sparing MMP-1, -3, and -9.
The synthesis and biological data for a series of novel acyclic phosphonamide-based inhibitors of TACE is reported.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>12781187</pmid><doi>10.1016/S0960-894X(03)00292-0</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Bioorganic & medicinal chemistry letters, 2003-06, Vol.13 (12), p.2021-2024 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | ADAM Proteins ADAM17 Protein Amides - chemistry Amides - pharmacology Binding Sites Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Drug Design Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Isomerism Matrix Metalloproteinase Inhibitors Matrix Metalloproteinases - metabolism Medical sciences Metalloendopeptidases - antagonists & inhibitors Models, Molecular Organophosphonates - chemistry Organophosphonates - pharmacology Pharmacology. Drug treatments Structure-Activity Relationship |
| title | Discovery of selective phosphonamide-based inhibitors of tumor necrosis factor-α converting enzyme (TACE) |
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