New non-hydroxamic ADAMTS-5 inhibitors based on the 1,2,4-triazole-3-thiol scaffold
In this Letter we describe the design, synthesis, screening, and optimization of a new family of ADAMTS-5 inhibitors. These inhibitors display an original 1,2,4-triazole-3-thiol scaffold as a putative zinc binding-group. In vitro results are rationalized by in silico docking of the compounds in ADAM...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-11, Vol.20 (21), p.6213-6216 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Maingot, Lucie Leroux, Florence Landry, Valérie Dumont, Julie Nagase, Hideaki Villoutreix, Bruno Sperandio, Olivier Deprez-Poulain, Rebecca Deprez, Benoit |
| description | In this Letter we describe the design, synthesis, screening, and optimization of a new family of ADAMTS-5 inhibitors. These inhibitors display an original 1,2,4-triazole-3-thiol scaffold as a putative zinc binding-group. In vitro results are rationalized by in silico docking of the compounds in ADAMTS-5’s crystal structure. |
| doi_str_mv | 10.1016/j.bmcl.2010.08.108 |
| format | Article |
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Drug treatments ; Protease Inhibitors - chemical synthesis ; Protease Inhibitors - chemistry ; Protease Inhibitors - pharmacology ; Protein Binding ; Protein Conformation ; Structure-Activity Relationship ; Triazol-5-thiol ; Triazoles - chemical synthesis ; Triazoles - chemistry ; Triazoles - pharmacology ; X-Ray Diffraction</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-11, Vol.20 (21), p.6213-6216</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c417t-3993f91fb0362227bf206f4f762746efb95e2995ad03387e14abef40b1428c5e3</citedby><cites>FETCH-LOGICAL-c417t-3993f91fb0362227bf206f4f762746efb95e2995ad03387e14abef40b1428c5e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X10012448$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23419239$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20846863$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maingot, Lucie</creatorcontrib><creatorcontrib>Leroux, Florence</creatorcontrib><creatorcontrib>Landry, Valérie</creatorcontrib><creatorcontrib>Dumont, Julie</creatorcontrib><creatorcontrib>Nagase, Hideaki</creatorcontrib><creatorcontrib>Villoutreix, Bruno</creatorcontrib><creatorcontrib>Sperandio, Olivier</creatorcontrib><creatorcontrib>Deprez-Poulain, Rebecca</creatorcontrib><creatorcontrib>Deprez, Benoit</creatorcontrib><title>New non-hydroxamic ADAMTS-5 inhibitors based on the 1,2,4-triazole-3-thiol scaffold</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>In this Letter we describe the design, synthesis, screening, and optimization of a new family of ADAMTS-5 inhibitors. These inhibitors display an original 1,2,4-triazole-3-thiol scaffold as a putative zinc binding-group. In vitro results are rationalized by in silico docking of the compounds in ADAMTS-5’s crystal structure.</description><subject>1,2,4-Triazol-3-thiol</subject><subject>ADAM Proteins - antagonists & inhibitors</subject><subject>ADAMTS-5</subject><subject>ADAMTS5 Protein</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Computer Simulation</subject><subject>Drug Evaluation, Preclinical</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>Medical sciences</subject><subject>Metalloprotease</subject><subject>Models, Molecular</subject><subject>Osteoarthritis - drug therapy</subject><subject>Pharmacology. Drug treatments</subject><subject>Protease Inhibitors - chemical synthesis</subject><subject>Protease Inhibitors - chemistry</subject><subject>Protease Inhibitors - pharmacology</subject><subject>Protein Binding</subject><subject>Protein Conformation</subject><subject>Structure-Activity Relationship</subject><subject>Triazol-5-thiol</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - pharmacology</subject><subject>X-Ray Diffraction</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAURS0EotPCH2CBskHd1IM_XhJbYjMqLVQqsGiR2FmO86zxKImLnYGWX49HM5QdrJ50de7V0yHkFWdLznjzdrPsRjcsBSsBUyVTT8iCQwNUAqufkgXTDaNKw7cjcpzzhjEODOA5ORJMQaMauSA3n_FnNcWJrh_6FO_tGFy1er_6dHtD6ypM69CFOaZcdTZjX8WpmtdY8TNxBnROwf6KA1JJ53WIQ5Wd9T4O_QvyzNsh48vDPSFfLy9uzz_S6y8frs5X19QBb2cqtZZec98x2Qgh2s4L1njwbSNaaNB3ukahdW17JqVqkYPt0APrOAjlapQn5HS_e5fi9y3m2YwhOxwGO2HcZqOUZBI0h_-Sbd1CrQtfSLEnXYo5J_TmLoXRpgfDmdlZNxuzs2521g1TJVOl9Powv-1G7B8rfzQX4M0BsEXS4JOdXMh_OQlcC6kL927PYdH2I2Ay2QWcHPYhoZtNH8O__vgN5IGdGg</recordid><startdate>20101101</startdate><enddate>20101101</enddate><creator>Maingot, Lucie</creator><creator>Leroux, Florence</creator><creator>Landry, Valérie</creator><creator>Dumont, Julie</creator><creator>Nagase, Hideaki</creator><creator>Villoutreix, Bruno</creator><creator>Sperandio, Olivier</creator><creator>Deprez-Poulain, Rebecca</creator><creator>Deprez, Benoit</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20101101</creationdate><title>New non-hydroxamic ADAMTS-5 inhibitors based on the 1,2,4-triazole-3-thiol scaffold</title><author>Maingot, Lucie ; Leroux, Florence ; Landry, Valérie ; Dumont, Julie ; Nagase, Hideaki ; Villoutreix, Bruno ; Sperandio, Olivier ; Deprez-Poulain, Rebecca ; Deprez, Benoit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-3993f91fb0362227bf206f4f762746efb95e2995ad03387e14abef40b1428c5e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>1,2,4-Triazol-3-thiol</topic><topic>ADAM Proteins - antagonists & inhibitors</topic><topic>ADAMTS-5</topic><topic>ADAMTS5 Protein</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Computer Simulation</topic><topic>Drug Evaluation, Preclinical</topic><topic>Humans</topic><topic>Indicators and Reagents</topic><topic>Medical sciences</topic><topic>Metalloprotease</topic><topic>Models, Molecular</topic><topic>Osteoarthritis - drug therapy</topic><topic>Pharmacology. 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| subjects | 1,2,4-Triazol-3-thiol ADAM Proteins - antagonists & inhibitors ADAMTS-5 ADAMTS5 Protein Binding Sites Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Computer Simulation Drug Evaluation, Preclinical Humans Indicators and Reagents Medical sciences Metalloprotease Models, Molecular Osteoarthritis - drug therapy Pharmacology. Drug treatments Protease Inhibitors - chemical synthesis Protease Inhibitors - chemistry Protease Inhibitors - pharmacology Protein Binding Protein Conformation Structure-Activity Relationship Triazol-5-thiol Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology X-Ray Diffraction |
| title | New non-hydroxamic ADAMTS-5 inhibitors based on the 1,2,4-triazole-3-thiol scaffold |
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