Discovery of 4-azaindoles as novel inhibitors of c-Met kinase
The SAR and X-ray crystal structure of a series of 4-azaindole inhibitors of c-Met kinase is reported. A series of 4-azaindole inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and series optimisation was performed on the basis of this s...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2009-05, Vol.19 (10), p.2780-2784 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Porter, John Lumb, Simon Franklin, Richard J. Gascon-Simorte, Jose M. Calmiano, Mark Riche, Kelly Le Lallemand, Bénédicte Keyaerts, Jean Edwards, Helen Maloney, Alison Delgado, Jean King, Lloyd Foley, Anne Lecomte, Fabien Reuberson, James Meier, Christoph Batchelor, Mark |
| description | The SAR and X-ray crystal structure of a series of 4-azaindole inhibitors of c-Met kinase is reported.
A series of 4-azaindole inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and series optimisation was performed on the basis of this structure. Future directions for series development are discussed. |
| doi_str_mv | 10.1016/j.bmcl.2009.03.110 |
| format | Article |
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A series of 4-azaindole inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and series optimisation was performed on the basis of this structure. Future directions for series development are discussed.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2009.03.110</identifier><identifier>PMID: 19369077</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Antineoplastic agents ; Azaindole ; Biological and medical sciences ; c-Met Kinase inhibitor ; Cell Line, Tumor ; Computer Simulation ; Crystallography, X-Ray ; Drug Discovery ; General aspects ; Hepatocyte growth factor receptor inhibitor ; Humans ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Kinase inhibitor ; Medical sciences ; Pharmacology. Drug treatments ; Protein Kinase Inhibitors - chemical synthesis ; Protein Kinase Inhibitors - chemistry ; Protein Kinase Inhibitors - pharmacology ; Proto-Oncogene Proteins c-met - antagonists & inhibitors ; Proto-Oncogene Proteins c-met - metabolism ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2009-05, Vol.19 (10), p.2780-2784</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c481t-de59dd9cae9bb1ea4db52e4fc3bfa3b69e7c73bec1f7a1d4c20e24d5fc75538d3</citedby><cites>FETCH-LOGICAL-c481t-de59dd9cae9bb1ea4db52e4fc3bfa3b69e7c73bec1f7a1d4c20e24d5fc75538d3</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.2009.03.110$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21496188$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19369077$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Porter, John</creatorcontrib><creatorcontrib>Lumb, Simon</creatorcontrib><creatorcontrib>Franklin, Richard J.</creatorcontrib><creatorcontrib>Gascon-Simorte, Jose M.</creatorcontrib><creatorcontrib>Calmiano, Mark</creatorcontrib><creatorcontrib>Riche, Kelly Le</creatorcontrib><creatorcontrib>Lallemand, Bénédicte</creatorcontrib><creatorcontrib>Keyaerts, Jean</creatorcontrib><creatorcontrib>Edwards, Helen</creatorcontrib><creatorcontrib>Maloney, Alison</creatorcontrib><creatorcontrib>Delgado, Jean</creatorcontrib><creatorcontrib>King, Lloyd</creatorcontrib><creatorcontrib>Foley, Anne</creatorcontrib><creatorcontrib>Lecomte, Fabien</creatorcontrib><creatorcontrib>Reuberson, James</creatorcontrib><creatorcontrib>Meier, Christoph</creatorcontrib><creatorcontrib>Batchelor, Mark</creatorcontrib><title>Discovery of 4-azaindoles as novel inhibitors of c-Met kinase</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The SAR and X-ray crystal structure of a series of 4-azaindole inhibitors of c-Met kinase is reported.
A series of 4-azaindole inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and series optimisation was performed on the basis of this structure. Future directions for series development are discussed.</description><subject>Antineoplastic agents</subject><subject>Azaindole</subject><subject>Biological and medical sciences</subject><subject>c-Met Kinase inhibitor</subject><subject>Cell Line, Tumor</subject><subject>Computer Simulation</subject><subject>Crystallography, X-Ray</subject><subject>Drug Discovery</subject><subject>General aspects</subject><subject>Hepatocyte growth factor receptor inhibitor</subject><subject>Humans</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Kinase inhibitor</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Kinase Inhibitors - chemical synthesis</subject><subject>Protein Kinase Inhibitors - chemistry</subject><subject>Protein Kinase Inhibitors - pharmacology</subject><subject>Proto-Oncogene Proteins c-met - antagonists & inhibitors</subject><subject>Proto-Oncogene Proteins c-met - metabolism</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtP3DAUha2Kqgy0f6ALlA3dJb03dpxYKgtEeVSaik0rdWf5cSM8zSRgZ5CGX0-iGcEOVndxv3N09DH2FaFAQPl9Vdi164oSQBXAC0T4wBYopMi5gOqALUBJyBsl_h2yo5RWAChAiE_sEBWXCup6wc5-huSGR4rbbGgzkZsnE3o_dJQyk7J--nRZ6O-CDeMQ08y4_DeN2f_Qm0Sf2cfWdIm-7O8x-3t1-efiJl_eXv-6OF_mTjQ45p4q5b1yhpS1SEZ4W5UkWsdta7iVimpXc0sO29qgF64EKoWvWldXFW88P2bfdr33cXjYUBr1eppNXWd6GjZJyxobqUTzLlhCJREaOYHlDnRxSClSq-9jWJu41Qh6tqtXerarZ7sauJ7sTqGTffvGrsm_RvY6J-B0D5jkTNdG07uQXrgShZLYzDN_7DiapD0Gijq5QL0jHyK5UfshvLXjGfG6mIQ</recordid><startdate>20090515</startdate><enddate>20090515</enddate><creator>Porter, John</creator><creator>Lumb, Simon</creator><creator>Franklin, Richard J.</creator><creator>Gascon-Simorte, Jose M.</creator><creator>Calmiano, Mark</creator><creator>Riche, Kelly Le</creator><creator>Lallemand, Bénédicte</creator><creator>Keyaerts, Jean</creator><creator>Edwards, Helen</creator><creator>Maloney, Alison</creator><creator>Delgado, Jean</creator><creator>King, Lloyd</creator><creator>Foley, Anne</creator><creator>Lecomte, Fabien</creator><creator>Reuberson, James</creator><creator>Meier, Christoph</creator><creator>Batchelor, Mark</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>20090515</creationdate><title>Discovery of 4-azaindoles as novel inhibitors of c-Met kinase</title><author>Porter, John ; Lumb, Simon ; Franklin, Richard J. ; Gascon-Simorte, Jose M. ; Calmiano, Mark ; Riche, Kelly Le ; Lallemand, Bénédicte ; Keyaerts, Jean ; Edwards, Helen ; Maloney, Alison ; Delgado, Jean ; King, Lloyd ; Foley, Anne ; Lecomte, Fabien ; Reuberson, James ; Meier, Christoph ; Batchelor, Mark</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c481t-de59dd9cae9bb1ea4db52e4fc3bfa3b69e7c73bec1f7a1d4c20e24d5fc75538d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Antineoplastic agents</topic><topic>Azaindole</topic><topic>Biological and medical sciences</topic><topic>c-Met Kinase inhibitor</topic><topic>Cell Line, Tumor</topic><topic>Computer Simulation</topic><topic>Crystallography, X-Ray</topic><topic>Drug Discovery</topic><topic>General aspects</topic><topic>Hepatocyte growth factor receptor inhibitor</topic><topic>Humans</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Kinase inhibitor</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Kinase Inhibitors - chemical synthesis</topic><topic>Protein Kinase Inhibitors - chemistry</topic><topic>Protein Kinase Inhibitors - pharmacology</topic><topic>Proto-Oncogene Proteins c-met - antagonists & inhibitors</topic><topic>Proto-Oncogene Proteins c-met - metabolism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Porter, John</creatorcontrib><creatorcontrib>Lumb, Simon</creatorcontrib><creatorcontrib>Franklin, Richard J.</creatorcontrib><creatorcontrib>Gascon-Simorte, Jose M.</creatorcontrib><creatorcontrib>Calmiano, Mark</creatorcontrib><creatorcontrib>Riche, Kelly Le</creatorcontrib><creatorcontrib>Lallemand, Bénédicte</creatorcontrib><creatorcontrib>Keyaerts, Jean</creatorcontrib><creatorcontrib>Edwards, Helen</creatorcontrib><creatorcontrib>Maloney, Alison</creatorcontrib><creatorcontrib>Delgado, Jean</creatorcontrib><creatorcontrib>King, Lloyd</creatorcontrib><creatorcontrib>Foley, Anne</creatorcontrib><creatorcontrib>Lecomte, Fabien</creatorcontrib><creatorcontrib>Reuberson, James</creatorcontrib><creatorcontrib>Meier, Christoph</creatorcontrib><creatorcontrib>Batchelor, Mark</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>Porter, John</au><au>Lumb, Simon</au><au>Franklin, Richard J.</au><au>Gascon-Simorte, Jose M.</au><au>Calmiano, Mark</au><au>Riche, Kelly Le</au><au>Lallemand, Bénédicte</au><au>Keyaerts, Jean</au><au>Edwards, Helen</au><au>Maloney, Alison</au><au>Delgado, Jean</au><au>King, Lloyd</au><au>Foley, Anne</au><au>Lecomte, Fabien</au><au>Reuberson, James</au><au>Meier, Christoph</au><au>Batchelor, Mark</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of 4-azaindoles as novel inhibitors of c-Met kinase</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009-05-15</date><risdate>2009</risdate><volume>19</volume><issue>10</issue><spage>2780</spage><epage>2784</epage><pages>2780-2784</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The SAR and X-ray crystal structure of a series of 4-azaindole inhibitors of c-Met kinase is reported.
A series of 4-azaindole inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and series optimisation was performed on the basis of this structure. Future directions for series development are discussed.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19369077</pmid><doi>10.1016/j.bmcl.2009.03.110</doi><tpages>5</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2009-05, Vol.19 (10), p.2780-2784 |
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| subjects | Antineoplastic agents Azaindole Biological and medical sciences c-Met Kinase inhibitor Cell Line, Tumor Computer Simulation Crystallography, X-Ray Drug Discovery General aspects Hepatocyte growth factor receptor inhibitor Humans Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Kinase inhibitor Medical sciences Pharmacology. Drug treatments Protein Kinase Inhibitors - chemical synthesis Protein Kinase Inhibitors - chemistry Protein Kinase Inhibitors - pharmacology Proto-Oncogene Proteins c-met - antagonists & inhibitors Proto-Oncogene Proteins c-met - metabolism Structure-Activity Relationship |
| title | Discovery of 4-azaindoles as novel inhibitors of c-Met kinase |
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