Syntheses and in vitro evaluation of arylsulfone-based MMP inhibitors with heterocycle-derived zinc-binding groups (ZBGs)
Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6-to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. The most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG....
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2008, Vol.18 (1), p.405-408 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Zhang, Yue-Mei Fan, Xiaodong Yang, Shyh-Ming Scannevin, Robert H. Burke, Sharon L. Rhodes, Kenneth J. Jackson, Paul F. |
| description | Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6-to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. The most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG.
Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6- to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. Although a number of 6- and 7-membered heterocycles were effective, the most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG. |
| doi_str_mv | 10.1016/j.bmcl.2007.10.049 |
| format | Article |
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Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6- to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. Although a number of 6- and 7-membered heterocycles were effective, the most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2007.10.049</identifier><identifier>PMID: 17980583</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Arylsulfone ; Biological and medical sciences ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - pharmacology ; Lactams - chemical synthesis ; Lactams - chemistry ; Lactams - pharmacology ; Matrix metalloproteinase inhibitor ; Matrix Metalloproteinase Inhibitors ; Medical sciences ; Miscellaneous ; MMP-2 ; MMP-9 ; Pharmacology. Drug treatments ; Protease Inhibitors - chemical synthesis ; Protease Inhibitors - chemistry ; Protease Inhibitors - pharmacology ; Pyridones - chemistry ; Pyridones - pharmacology ; Structure-Activity Relationship ; Sulfones - chemical synthesis ; Sulfones - chemistry ; Sulfones - pharmacology ; Zinc - chemistry ; Zinc-binding group</subject><ispartof>Bioorganic & medicinal chemistry letters, 2008, Vol.18 (1), p.405-408</ispartof><rights>2007 Elsevier Ltd</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-d17b175743703cdddcfa71af20a11c153159826548046d12897aef88138aa1883</citedby><cites>FETCH-LOGICAL-c384t-d17b175743703cdddcfa71af20a11c153159826548046d12897aef88138aa1883</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2007.10.049$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,4009,27902,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20037457$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17980583$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Yue-Mei</creatorcontrib><creatorcontrib>Fan, Xiaodong</creatorcontrib><creatorcontrib>Yang, Shyh-Ming</creatorcontrib><creatorcontrib>Scannevin, Robert H.</creatorcontrib><creatorcontrib>Burke, Sharon L.</creatorcontrib><creatorcontrib>Rhodes, Kenneth J.</creatorcontrib><creatorcontrib>Jackson, Paul F.</creatorcontrib><title>Syntheses and in vitro evaluation of arylsulfone-based MMP inhibitors with heterocycle-derived zinc-binding groups (ZBGs)</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6-to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. The most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG.
Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6- to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. Although a number of 6- and 7-membered heterocycles were effective, the most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG.</description><subject>Arylsulfone</subject><subject>Biological and medical sciences</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - pharmacology</subject><subject>Lactams - chemical synthesis</subject><subject>Lactams - chemistry</subject><subject>Lactams - pharmacology</subject><subject>Matrix metalloproteinase inhibitor</subject><subject>Matrix Metalloproteinase Inhibitors</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>MMP-2</subject><subject>MMP-9</subject><subject>Pharmacology. Drug treatments</subject><subject>Protease Inhibitors - chemical synthesis</subject><subject>Protease Inhibitors - chemistry</subject><subject>Protease Inhibitors - pharmacology</subject><subject>Pyridones - chemistry</subject><subject>Pyridones - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Sulfones - chemical synthesis</subject><subject>Sulfones - chemistry</subject><subject>Sulfones - pharmacology</subject><subject>Zinc - chemistry</subject><subject>Zinc-binding group</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMGKFDEQhoMo7uzqC3iQXJT10GOqO91Jw1500VXYRUEF8RLSSfVOhp5kTNIj49ObYQa9eSoovv-n6iPkGbAlMOher5fDxkzLmjFRFkvG-wdkAbzjVcNZ-5AsWN-xSvb8-xk5T2nNGHDG-WNyBqKXrJXNguy_7H1eYcJEtbfUebpzOQaKOz3NOrvgaRipjvspzdMYPFaDTmjp3d3nAq_c4HKIif5yeUVXmDEGszcTVhaj2xXut_OmGpy3zt_T-xjmbaKXP97epFdPyKNRTwmfnuYF-fb-3dfrD9Xtp5uP129uK9NInisLYgDRCt4I1hhrrRm1AD3WTAMYaBtoe1l3LZeMdxZq2QuNo5TQSK1ByuaCvDz2bmP4OWPKauOSwWnSHsOclGDQCw51AesjaGJIKeKottFtyusKmDoIV2t1EK4Owg-7IryEnp_a52GD9l_kZLgAL06ATkZPY9TeuPSXK12N4K0o3NWRw-Ji5zCqZBx6g9ZFNFnZ4P53xx8PSp9i</recordid><startdate>2008</startdate><enddate>2008</enddate><creator>Zhang, Yue-Mei</creator><creator>Fan, Xiaodong</creator><creator>Yang, Shyh-Ming</creator><creator>Scannevin, Robert H.</creator><creator>Burke, Sharon L.</creator><creator>Rhodes, Kenneth J.</creator><creator>Jackson, Paul F.</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>2008</creationdate><title>Syntheses and in vitro evaluation of arylsulfone-based MMP inhibitors with heterocycle-derived zinc-binding groups (ZBGs)</title><author>Zhang, Yue-Mei ; Fan, Xiaodong ; Yang, Shyh-Ming ; Scannevin, Robert H. ; Burke, Sharon L. ; Rhodes, Kenneth J. ; Jackson, Paul F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-d17b175743703cdddcfa71af20a11c153159826548046d12897aef88138aa1883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Arylsulfone</topic><topic>Biological and medical sciences</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - pharmacology</topic><topic>Lactams - chemical synthesis</topic><topic>Lactams - chemistry</topic><topic>Lactams - pharmacology</topic><topic>Matrix metalloproteinase inhibitor</topic><topic>Matrix Metalloproteinase Inhibitors</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>MMP-2</topic><topic>MMP-9</topic><topic>Pharmacology. Drug treatments</topic><topic>Protease Inhibitors - chemical synthesis</topic><topic>Protease Inhibitors - chemistry</topic><topic>Protease Inhibitors - pharmacology</topic><topic>Pyridones - chemistry</topic><topic>Pyridones - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Sulfones - chemical synthesis</topic><topic>Sulfones - chemistry</topic><topic>Sulfones - pharmacology</topic><topic>Zinc - chemistry</topic><topic>Zinc-binding group</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Yue-Mei</creatorcontrib><creatorcontrib>Fan, Xiaodong</creatorcontrib><creatorcontrib>Yang, Shyh-Ming</creatorcontrib><creatorcontrib>Scannevin, Robert H.</creatorcontrib><creatorcontrib>Burke, Sharon L.</creatorcontrib><creatorcontrib>Rhodes, Kenneth J.</creatorcontrib><creatorcontrib>Jackson, Paul F.</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>Zhang, Yue-Mei</au><au>Fan, Xiaodong</au><au>Yang, Shyh-Ming</au><au>Scannevin, Robert H.</au><au>Burke, Sharon L.</au><au>Rhodes, Kenneth J.</au><au>Jackson, Paul F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and in vitro evaluation of arylsulfone-based MMP inhibitors with heterocycle-derived zinc-binding groups (ZBGs)</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2008</date><risdate>2008</risdate><volume>18</volume><issue>1</issue><spage>405</spage><epage>408</epage><pages>405-408</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6-to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. The most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG.
Several classes of arylsulfone-based MMP-2/-9 inhibitors utilizing 6- to 8-membered heterocyclic rings as zinc-binding groups (ZBGs) have been synthesized and their enzyme inhibitory activities were evaluated. Although a number of 6- and 7-membered heterocycles were effective, the most potent arylsulfone inhibitors are based on the rigid 1- or 3-hydroxypyridone ZBG.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17980583</pmid><doi>10.1016/j.bmcl.2007.10.049</doi><tpages>4</tpages></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Arylsulfone Biological and medical sciences Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic Compounds - pharmacology Lactams - chemical synthesis Lactams - chemistry Lactams - pharmacology Matrix metalloproteinase inhibitor Matrix Metalloproteinase Inhibitors Medical sciences Miscellaneous MMP-2 MMP-9 Pharmacology. Drug treatments Protease Inhibitors - chemical synthesis Protease Inhibitors - chemistry Protease Inhibitors - pharmacology Pyridones - chemistry Pyridones - pharmacology Structure-Activity Relationship Sulfones - chemical synthesis Sulfones - chemistry Sulfones - pharmacology Zinc - chemistry Zinc-binding group |
| title | Syntheses and in vitro evaluation of arylsulfone-based MMP inhibitors with heterocycle-derived zinc-binding groups (ZBGs) |
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