Identification of a novel series of potent RON receptor tyrosine kinase inhibitors
A novel series of N-(3-fluoro-4-(2-substituted-thieno[3,2- b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1 H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory act...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-05, Vol.20 (9), p.2745-2749 |
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| creator | Raeppel, Stéphane Gaudette, Frédéric Mannion, Michael Claridge, Stephen Saavedra, Oscar Isakovic, Ljubomir Déziel, Robert Beaulieu, Normand Beaulieu, Carole Dupont, Isabelle Nguyen, Hannah Wang, James Macleod, A. Robert Maroun, Christiane Besterman, Jeffrey M. Vaisburg, Arkadii |
| description | A novel series of
N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases.
A novel series of
N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases. |
| doi_str_mv | 10.1016/j.bmcl.2010.03.073 |
| format | Article |
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N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases.
A novel series of
N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.03.073</identifier><identifier>PMID: 20363625</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacokinetics ; Biological and medical sciences ; c-Met ; Cell Line, Tumor ; General aspects ; Heterocyclic Compounds, 2-Ring - chemical synthesis ; Heterocyclic Compounds, 2-Ring - chemistry ; Heterocyclic Compounds, 2-Ring - pharmacokinetics ; Humans ; Medical sciences ; Oncology ; Pharmacology. Drug treatments ; Protein Kinase Inhibitors - chemical synthesis ; Protein Kinase Inhibitors - chemistry ; Protein Kinase Inhibitors - pharmacokinetics ; Proto-Oncogene Proteins c-met - antagonists & inhibitors ; Proto-Oncogene Proteins c-met - metabolism ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacokinetics ; Rats ; Receptor Protein-Tyrosine Kinases - antagonists & inhibitors ; Receptor Protein-Tyrosine Kinases - metabolism ; RON ; RTK inhibitors ; Structure-Activity Relationship ; Thieno[3,2- b]pyridine</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-05, Vol.20 (9), p.2745-2749</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c417t-da55eb7a51914c882053f83f11f012f8c5bac195921b0f08bd2f9660ee4ba9d03</citedby><cites>FETCH-LOGICAL-c417t-da55eb7a51914c882053f83f11f012f8c5bac195921b0f08bd2f9660ee4ba9d03</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.2010.03.073$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22824996$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20363625$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Raeppel, Stéphane</creatorcontrib><creatorcontrib>Gaudette, Frédéric</creatorcontrib><creatorcontrib>Mannion, Michael</creatorcontrib><creatorcontrib>Claridge, Stephen</creatorcontrib><creatorcontrib>Saavedra, Oscar</creatorcontrib><creatorcontrib>Isakovic, Ljubomir</creatorcontrib><creatorcontrib>Déziel, Robert</creatorcontrib><creatorcontrib>Beaulieu, Normand</creatorcontrib><creatorcontrib>Beaulieu, Carole</creatorcontrib><creatorcontrib>Dupont, Isabelle</creatorcontrib><creatorcontrib>Nguyen, Hannah</creatorcontrib><creatorcontrib>Wang, James</creatorcontrib><creatorcontrib>Macleod, A. Robert</creatorcontrib><creatorcontrib>Maroun, Christiane</creatorcontrib><creatorcontrib>Besterman, Jeffrey M.</creatorcontrib><creatorcontrib>Vaisburg, Arkadii</creatorcontrib><title>Identification of a novel series of potent RON receptor tyrosine kinase inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A novel series of
N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases.
A novel series of
N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacokinetics</subject><subject>Biological and medical sciences</subject><subject>c-Met</subject><subject>Cell Line, Tumor</subject><subject>General aspects</subject><subject>Heterocyclic Compounds, 2-Ring - chemical synthesis</subject><subject>Heterocyclic Compounds, 2-Ring - chemistry</subject><subject>Heterocyclic Compounds, 2-Ring - pharmacokinetics</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Oncology</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Kinase Inhibitors - chemical synthesis</subject><subject>Protein Kinase Inhibitors - chemistry</subject><subject>Protein Kinase Inhibitors - pharmacokinetics</subject><subject>Proto-Oncogene Proteins c-met - antagonists & inhibitors</subject><subject>Proto-Oncogene Proteins c-met - metabolism</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacokinetics</subject><subject>Rats</subject><subject>Receptor Protein-Tyrosine Kinases - antagonists & inhibitors</subject><subject>Receptor Protein-Tyrosine Kinases - metabolism</subject><subject>RON</subject><subject>RTK inhibitors</subject><subject>Structure-Activity Relationship</subject><subject>Thieno[3,2- b]pyridine</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>eNqFkE2LFDEQhoMo7rj6BzxILuKpx8pnd8CLLKu7sLiwKHgL6XQFM_YkY9KzsP_eDDOuNz0VvPVUUfUQ8prBmgHT7zfrcevnNYcWgFhDL56QFZNadkKCekpWYDR0g5Hfz8iLWjcATIKUz8kZB6GF5mpF7q4nTEsM0bsl5kRzoI6mfI8zrVgi1kOyy0uD6N3tF1rQ427JhS4PJdeYkP6MyVWkMf2IY2yd-pI8C26u-OpUz8m3T5dfL666m9vP1xcfbzovWb90k1MKx94pZpj0w8BBiTCIwFgAxsPg1eg8M8pwNkKAYZx4MFoDohydmUCck3fHvbuSf-2xLnYbq8d5dgnzvtpeqp5Bb9j_SSEG03NtGsmPpG_f1YLB7krcuvJgGdiDdLuxB-n2IN2CsE16G3pzWr8ftzg9jvyx3IC3J8BV7-ZQXPKx_uX4wKUxunEfjhw2bfcRi60-YvI4xeZ9sVOO_7rjN6P_n5g</recordid><startdate>20100501</startdate><enddate>20100501</enddate><creator>Raeppel, Stéphane</creator><creator>Gaudette, Frédéric</creator><creator>Mannion, Michael</creator><creator>Claridge, Stephen</creator><creator>Saavedra, Oscar</creator><creator>Isakovic, Ljubomir</creator><creator>Déziel, Robert</creator><creator>Beaulieu, Normand</creator><creator>Beaulieu, Carole</creator><creator>Dupont, Isabelle</creator><creator>Nguyen, Hannah</creator><creator>Wang, James</creator><creator>Macleod, A. Robert</creator><creator>Maroun, Christiane</creator><creator>Besterman, Jeffrey M.</creator><creator>Vaisburg, Arkadii</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>20100501</creationdate><title>Identification of a novel series of potent RON receptor tyrosine kinase inhibitors</title><author>Raeppel, Stéphane ; Gaudette, Frédéric ; Mannion, Michael ; Claridge, Stephen ; Saavedra, Oscar ; Isakovic, Ljubomir ; Déziel, Robert ; Beaulieu, Normand ; Beaulieu, Carole ; Dupont, Isabelle ; Nguyen, Hannah ; Wang, James ; Macleod, A. Robert ; Maroun, Christiane ; Besterman, Jeffrey M. ; Vaisburg, Arkadii</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-da55eb7a51914c882053f83f11f012f8c5bac195921b0f08bd2f9660ee4ba9d03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacokinetics</topic><topic>Biological and medical sciences</topic><topic>c-Met</topic><topic>Cell Line, Tumor</topic><topic>General aspects</topic><topic>Heterocyclic Compounds, 2-Ring - chemical synthesis</topic><topic>Heterocyclic Compounds, 2-Ring - chemistry</topic><topic>Heterocyclic Compounds, 2-Ring - pharmacokinetics</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Oncology</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Kinase Inhibitors - chemical synthesis</topic><topic>Protein Kinase Inhibitors - chemistry</topic><topic>Protein Kinase Inhibitors - pharmacokinetics</topic><topic>Proto-Oncogene Proteins c-met - antagonists & inhibitors</topic><topic>Proto-Oncogene Proteins c-met - metabolism</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacokinetics</topic><topic>Rats</topic><topic>Receptor Protein-Tyrosine Kinases - antagonists & inhibitors</topic><topic>Receptor Protein-Tyrosine Kinases - metabolism</topic><topic>RON</topic><topic>RTK inhibitors</topic><topic>Structure-Activity Relationship</topic><topic>Thieno[3,2- b]pyridine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Raeppel, Stéphane</creatorcontrib><creatorcontrib>Gaudette, Frédéric</creatorcontrib><creatorcontrib>Mannion, Michael</creatorcontrib><creatorcontrib>Claridge, Stephen</creatorcontrib><creatorcontrib>Saavedra, Oscar</creatorcontrib><creatorcontrib>Isakovic, Ljubomir</creatorcontrib><creatorcontrib>Déziel, Robert</creatorcontrib><creatorcontrib>Beaulieu, Normand</creatorcontrib><creatorcontrib>Beaulieu, Carole</creatorcontrib><creatorcontrib>Dupont, Isabelle</creatorcontrib><creatorcontrib>Nguyen, Hannah</creatorcontrib><creatorcontrib>Wang, James</creatorcontrib><creatorcontrib>Macleod, A. Robert</creatorcontrib><creatorcontrib>Maroun, Christiane</creatorcontrib><creatorcontrib>Besterman, Jeffrey M.</creatorcontrib><creatorcontrib>Vaisburg, Arkadii</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Raeppel, Stéphane</au><au>Gaudette, Frédéric</au><au>Mannion, Michael</au><au>Claridge, Stephen</au><au>Saavedra, Oscar</au><au>Isakovic, Ljubomir</au><au>Déziel, Robert</au><au>Beaulieu, Normand</au><au>Beaulieu, Carole</au><au>Dupont, Isabelle</au><au>Nguyen, Hannah</au><au>Wang, James</au><au>Macleod, A. Robert</au><au>Maroun, Christiane</au><au>Besterman, Jeffrey M.</au><au>Vaisburg, Arkadii</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of a novel series of potent RON receptor tyrosine kinase inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-05-01</date><risdate>2010</risdate><volume>20</volume><issue>9</issue><spage>2745</spage><epage>2749</epage><pages>2745-2749</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A novel series of
N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases.
A novel series of
N-(3-fluoro-4-(2-substituted-thieno[3,2-
b]pyridin-7-yloxy)phenyl)-1-phenyl-5-(trifluoromethyl)-1
H-pyrazole-4-carboxamides targeting RON receptor tyrosine kinase was designed and synthesized. SAR study of the series allowed us to identify compounds possessing either inhibitory activity of RON kinase enzyme in the low nanomolar range with low residual activity against the closely related c-Met or potent dual inhibitory activity against RON and c-Met, − with no significant activity against VEGFR2 in both cases.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20363625</pmid><doi>10.1016/j.bmcl.2010.03.073</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2010-05, Vol.20 (9), p.2745-2749 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_745710791 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacokinetics Biological and medical sciences c-Met Cell Line, Tumor General aspects Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Heterocyclic Compounds, 2-Ring - pharmacokinetics Humans Medical sciences Oncology Pharmacology. Drug treatments Protein Kinase Inhibitors - chemical synthesis Protein Kinase Inhibitors - chemistry Protein Kinase Inhibitors - pharmacokinetics Proto-Oncogene Proteins c-met - antagonists & inhibitors Proto-Oncogene Proteins c-met - metabolism Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacokinetics Rats Receptor Protein-Tyrosine Kinases - antagonists & inhibitors Receptor Protein-Tyrosine Kinases - metabolism RON RTK inhibitors Structure-Activity Relationship Thieno[3,2- b]pyridine |
| title | Identification of a novel series of potent RON receptor tyrosine kinase inhibitors |
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