Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors
A series of butynyloxyphenyl β-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure–activity relationship and MMP selectivity of the series were examined. Of the compounds investigated, 17s has excellent in vitro potency against isolated TACE enzyme, s...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-08, Vol.16 (15), p.3927-3931 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3931 |
|---|---|
| container_issue | 15 |
| container_start_page | 3927 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 16 |
| creator | Park, Kaapjoo Aplasca, Alexis Du, Mila T. Sun, LinHong Zhu, Yi Zhang, Yuhua Levin, Jeremy I. |
| description | A series of butynyloxyphenyl β-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure–activity relationship and MMP selectivity of the series were examined. Of the compounds investigated,
17s has excellent in vitro potency against isolated TACE enzyme, shows good selectivity over MMP-1, -2, -7, -8, -9, -13, and -14, and oral activity in an in vivo mouse model of TNF-α production. |
| doi_str_mv | 10.1016/j.bmcl.2006.05.026 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68095708</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X06005713</els_id><sourcerecordid>17218522</sourcerecordid><originalsourceid>FETCH-LOGICAL-c415t-18d283562282b4954833a8b26eecf8e59b9f1cb4e1ee58060af79db21e587b963</originalsourceid><addsrcrecordid>eNqFkM9u1DAQhy0EotvCC3BAucAt6dixHVviUi2lIFXqpZU4YdnOhPUq_7AT1LwWD8IzkdWu1Bs9zYz0_X4afYS8o1BQoPJyX7jOtwUDkAWIAph8QTaUS56XHMRLsgEtIVeafz8j5yntASgHzl-TMyorVjKmN-THZ0zhZ5_Zvs7S0k-79UzZ0GRunpZ-aYfHZdzhumR__-Rpbpuhx2wMI8ZQh3XdLXUcHm1nJ0yZTdn91fY6C_0uuDANMb0hrxrbJnx7mhfk4cv1_fZrfnt38217dZt7TsWUU1UzVQrJmGKOa8FVWVrlmET0jUKhnW6odxwpolAgwTaVrh2j61U5LcsL8vHYO8bh14xpMl1IHtvW9jjMyUgFWlSgngVpxagSjK0gO4I-DilFbMwYQ2fjYiiYg36zNwf95qDfgDCr_jX0_tQ-uw7rp8jJ9wp8OAE2eds20fY-pCeu0iAYPxR9OnK4SvsdMJrkA_Ye6xDRT6Yewv_--Ad24KTI</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>17218522</pqid></control><display><type>article</type><title>Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Park, Kaapjoo ; Aplasca, Alexis ; Du, Mila T. ; Sun, LinHong ; Zhu, Yi ; Zhang, Yuhua ; Levin, Jeremy I.</creator><creatorcontrib>Park, Kaapjoo ; Aplasca, Alexis ; Du, Mila T. ; Sun, LinHong ; Zhu, Yi ; Zhang, Yuhua ; Levin, Jeremy I.</creatorcontrib><description>A series of butynyloxyphenyl β-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure–activity relationship and MMP selectivity of the series were examined. Of the compounds investigated,
17s has excellent in vitro potency against isolated TACE enzyme, shows good selectivity over MMP-1, -2, -7, -8, -9, -13, and -14, and oral activity in an in vivo mouse model of TNF-α production.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2006.05.026</identifier><identifier>PMID: 16723229</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>ADAM Proteins - antagonists & inhibitors ; ADAM17 Protein ; Animals ; Biological and medical sciences ; Drug Design ; Medical sciences ; Mice ; Miscellaneous ; MMP selectivity ; Pharmacology. Drug treatments ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Piperidines - pharmacology ; Structure-Activity Relationship ; TACE inhibitors ; β-Sulfone piperidine hydroxamates</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-08, Vol.16 (15), p.3927-3931</ispartof><rights>2006 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-18d283562282b4954833a8b26eecf8e59b9f1cb4e1ee58060af79db21e587b963</citedby><cites>FETCH-LOGICAL-c415t-18d283562282b4954833a8b26eecf8e59b9f1cb4e1ee58060af79db21e587b963</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X06005713$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17905246$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16723229$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Park, Kaapjoo</creatorcontrib><creatorcontrib>Aplasca, Alexis</creatorcontrib><creatorcontrib>Du, Mila T.</creatorcontrib><creatorcontrib>Sun, LinHong</creatorcontrib><creatorcontrib>Zhu, Yi</creatorcontrib><creatorcontrib>Zhang, Yuhua</creatorcontrib><creatorcontrib>Levin, Jeremy I.</creatorcontrib><title>Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of butynyloxyphenyl β-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure–activity relationship and MMP selectivity of the series were examined. Of the compounds investigated,
17s has excellent in vitro potency against isolated TACE enzyme, shows good selectivity over MMP-1, -2, -7, -8, -9, -13, and -14, and oral activity in an in vivo mouse model of TNF-α production.</description><subject>ADAM Proteins - antagonists & inhibitors</subject><subject>ADAM17 Protein</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Drug Design</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Miscellaneous</subject><subject>MMP selectivity</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>TACE inhibitors</subject><subject>β-Sulfone piperidine hydroxamates</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM9u1DAQhy0EotvCC3BAucAt6dixHVviUi2lIFXqpZU4YdnOhPUq_7AT1LwWD8IzkdWu1Bs9zYz0_X4afYS8o1BQoPJyX7jOtwUDkAWIAph8QTaUS56XHMRLsgEtIVeafz8j5yntASgHzl-TMyorVjKmN-THZ0zhZ5_Zvs7S0k-79UzZ0GRunpZ-aYfHZdzhumR__-Rpbpuhx2wMI8ZQh3XdLXUcHm1nJ0yZTdn91fY6C_0uuDANMb0hrxrbJnx7mhfk4cv1_fZrfnt38217dZt7TsWUU1UzVQrJmGKOa8FVWVrlmET0jUKhnW6odxwpolAgwTaVrh2j61U5LcsL8vHYO8bh14xpMl1IHtvW9jjMyUgFWlSgngVpxagSjK0gO4I-DilFbMwYQ2fjYiiYg36zNwf95qDfgDCr_jX0_tQ-uw7rp8jJ9wp8OAE2eds20fY-pCeu0iAYPxR9OnK4SvsdMJrkA_Ye6xDRT6Yewv_--Ad24KTI</recordid><startdate>20060801</startdate><enddate>20060801</enddate><creator>Park, Kaapjoo</creator><creator>Aplasca, Alexis</creator><creator>Du, Mila T.</creator><creator>Sun, LinHong</creator><creator>Zhu, Yi</creator><creator>Zhang, Yuhua</creator><creator>Levin, Jeremy I.</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20060801</creationdate><title>Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors</title><author>Park, Kaapjoo ; Aplasca, Alexis ; Du, Mila T. ; Sun, LinHong ; Zhu, Yi ; Zhang, Yuhua ; Levin, Jeremy I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-18d283562282b4954833a8b26eecf8e59b9f1cb4e1ee58060af79db21e587b963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>ADAM Proteins - antagonists & inhibitors</topic><topic>ADAM17 Protein</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Drug Design</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Miscellaneous</topic><topic>MMP selectivity</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>TACE inhibitors</topic><topic>β-Sulfone piperidine hydroxamates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Kaapjoo</creatorcontrib><creatorcontrib>Aplasca, Alexis</creatorcontrib><creatorcontrib>Du, Mila T.</creatorcontrib><creatorcontrib>Sun, LinHong</creatorcontrib><creatorcontrib>Zhu, Yi</creatorcontrib><creatorcontrib>Zhang, Yuhua</creatorcontrib><creatorcontrib>Levin, Jeremy I.</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Park, Kaapjoo</au><au>Aplasca, Alexis</au><au>Du, Mila T.</au><au>Sun, LinHong</au><au>Zhu, Yi</au><au>Zhang, Yuhua</au><au>Levin, Jeremy I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-08-01</date><risdate>2006</risdate><volume>16</volume><issue>15</issue><spage>3927</spage><epage>3931</epage><pages>3927-3931</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of butynyloxyphenyl β-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure–activity relationship and MMP selectivity of the series were examined. Of the compounds investigated,
17s has excellent in vitro potency against isolated TACE enzyme, shows good selectivity over MMP-1, -2, -7, -8, -9, -13, and -14, and oral activity in an in vivo mouse model of TNF-α production.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16723229</pmid><doi>10.1016/j.bmcl.2006.05.026</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2006-08, Vol.16 (15), p.3927-3931 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68095708 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | ADAM Proteins - antagonists & inhibitors ADAM17 Protein Animals Biological and medical sciences Drug Design Medical sciences Mice Miscellaneous MMP selectivity Pharmacology. Drug treatments Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Structure-Activity Relationship TACE inhibitors β-Sulfone piperidine hydroxamates |
| title | Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T16%3A27%3A23IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Design%20and%20synthesis%20of%20butynyloxyphenyl%20%CE%B2-sulfone%20piperidine%20hydroxamates%20as%20TACE%20inhibitors&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Park,%20Kaapjoo&rft.date=2006-08-01&rft.volume=16&rft.issue=15&rft.spage=3927&rft.epage=3931&rft.pages=3927-3931&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2006.05.026&rft_dat=%3Cproquest_cross%3E17218522%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=17218522&rft_id=info:pmid/16723229&rft_els_id=S0960894X06005713&rfr_iscdi=true |