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Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1- f][1,2,4]triazine based VEGFR-2 kinase inhibitors
[Display omitted] A versatile synthesis of the suitably functionalized pyrrolo[2,1- f][1,2,4]triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1- f][1,2,4]triazine template led to compounds with good in vitro potency against VEGFR-2 kin...
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| Published in: | Bioorganic & medicinal chemistry letters 2005-03, Vol.15 (5), p.1429-1433 |
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| Main Authors: | , , , , , , , , , , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c384t-40da8b94221143f9dc13a2e0b34d747b0934302ec3675f211890f14deb57c2ea3 |
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| cites | cdi_FETCH-LOGICAL-c384t-40da8b94221143f9dc13a2e0b34d747b0934302ec3675f211890f14deb57c2ea3 |
| container_end_page | 1433 |
| container_issue | 5 |
| container_start_page | 1429 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 15 |
| creator | Borzilleri, Robert M. Cai, Zhen-wei Ellis, Christopher Fargnoli, Joseph Fura, Aberra Gerhardt, Tracy Goyal, Bindu Hunt, John T. Mortillo, Steven Qian, Ligang Tokarski, John Vyas, Viral Wautlet, Barri Zheng, Xioping Bhide, Rajeev S. |
| description | [Display omitted]
A versatile synthesis of the suitably functionalized pyrrolo[2,1-
f][1,2,4]triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1-
f][1,2,4]triazine template led to compounds with good in vitro potency against VEGFR-2 kinase. Glucuronidation of the phenol group is mitigated by incorporation of a basic amino group on the C-6 side chain of the pyrrolotriazine nucleus. |
| doi_str_mv | 10.1016/j.bmcl.2004.12.079 |
| format | article |
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A versatile synthesis of the suitably functionalized pyrrolo[2,1-
f][1,2,4]triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1-
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A versatile synthesis of the suitably functionalized pyrrolo[2,1-
f][1,2,4]triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1-
f][1,2,4]triazine template led to compounds with good in vitro potency against VEGFR-2 kinase. 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Drug treatments</subject><subject>Protein Binding</subject><subject>SAR</subject><subject>Structure-Activity Relationship</subject><subject>Triazines - chemical synthesis</subject><subject>Triazines - chemistry</subject><subject>Triazines - pharmacology</subject><subject>Vascular Endothelial Growth Factor Receptor-2 - antagonists & inhibitors</subject><subject>VEGFR-2</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNp9kF1rFDEUhoModq3-AS8kN5YWNmO-5gu8KaWtQkFoVYRSQiY5w2Y7k6zJrDj--mbZhd55dXjheV8OD0LvGS0YZdWnddGNZig4pbJgvKB1-wItmKwkEZKWL9GCthUlTSt_HaE3Ka0pZZJK-RodsbJmmWEL9Hg3-2kFySWsvcV357c49FiSU0FWs43h77xZgZ8HPTofzjZzjGEI93zJCO4f7tmSL-XDFJ3-5zzgTiew-Ofl9dUt4fjR-Zyx8yvXuSnE9Ba96vWQ4N3hHqMfV5ffL76Qm2_XXy_Ob4gRjZyIpFY3XSs5Z0yKvrWGCc2BdkLaWtYdbYUUlIMRVV32GWpa2jNpoStrw0GLY3Sy393E8HsLaVKjSwaGQXsI26SqOvfbssog34MmhpQi9GoT3ajjrBhVO8VqrXaK1U6xYlxlxbn04bC-7Uawz5WD0wx8PAA6GT30UXvj0jNXlWXDm93Q5z0H2cUfB1El48AbsC6CmZQN7n9_PAHecJes</recordid><startdate>20050301</startdate><enddate>20050301</enddate><creator>Borzilleri, Robert M.</creator><creator>Cai, Zhen-wei</creator><creator>Ellis, Christopher</creator><creator>Fargnoli, Joseph</creator><creator>Fura, Aberra</creator><creator>Gerhardt, Tracy</creator><creator>Goyal, Bindu</creator><creator>Hunt, John T.</creator><creator>Mortillo, Steven</creator><creator>Qian, Ligang</creator><creator>Tokarski, John</creator><creator>Vyas, Viral</creator><creator>Wautlet, Barri</creator><creator>Zheng, Xioping</creator><creator>Bhide, Rajeev S.</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>20050301</creationdate><title>Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1- f][1,2,4]triazine based VEGFR-2 kinase inhibitors</title><author>Borzilleri, Robert M. ; Cai, Zhen-wei ; Ellis, Christopher ; Fargnoli, Joseph ; Fura, Aberra ; Gerhardt, Tracy ; Goyal, Bindu ; Hunt, John T. ; Mortillo, Steven ; Qian, Ligang ; Tokarski, John ; Vyas, Viral ; Wautlet, Barri ; Zheng, Xioping ; Bhide, Rajeev S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-40da8b94221143f9dc13a2e0b34d747b0934302ec3675f211890f14deb57c2ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Angiogenesis</topic><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Biological and medical sciences</topic><topic>Cell Survival - drug effects</topic><topic>Endothelium, Vascular - drug effects</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>General aspects</topic><topic>Humans</topic><topic>Kinase receptor</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Microsomes, Liver - drug effects</topic><topic>Microsomes, Liver - metabolism</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Binding</topic><topic>SAR</topic><topic>Structure-Activity Relationship</topic><topic>Triazines - chemical synthesis</topic><topic>Triazines - chemistry</topic><topic>Triazines - pharmacology</topic><topic>Vascular Endothelial Growth Factor Receptor-2 - antagonists & inhibitors</topic><topic>VEGFR-2</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Borzilleri, Robert M.</creatorcontrib><creatorcontrib>Cai, Zhen-wei</creatorcontrib><creatorcontrib>Ellis, Christopher</creatorcontrib><creatorcontrib>Fargnoli, Joseph</creatorcontrib><creatorcontrib>Fura, Aberra</creatorcontrib><creatorcontrib>Gerhardt, Tracy</creatorcontrib><creatorcontrib>Goyal, Bindu</creatorcontrib><creatorcontrib>Hunt, John T.</creatorcontrib><creatorcontrib>Mortillo, Steven</creatorcontrib><creatorcontrib>Qian, Ligang</creatorcontrib><creatorcontrib>Tokarski, John</creatorcontrib><creatorcontrib>Vyas, Viral</creatorcontrib><creatorcontrib>Wautlet, Barri</creatorcontrib><creatorcontrib>Zheng, Xioping</creatorcontrib><creatorcontrib>Bhide, Rajeev S.</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>Borzilleri, Robert M.</au><au>Cai, Zhen-wei</au><au>Ellis, Christopher</au><au>Fargnoli, Joseph</au><au>Fura, Aberra</au><au>Gerhardt, Tracy</au><au>Goyal, Bindu</au><au>Hunt, John T.</au><au>Mortillo, Steven</au><au>Qian, Ligang</au><au>Tokarski, John</au><au>Vyas, Viral</au><au>Wautlet, Barri</au><au>Zheng, Xioping</au><au>Bhide, Rajeev S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1- f][1,2,4]triazine based VEGFR-2 kinase inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2005-03-01</date><risdate>2005</risdate><volume>15</volume><issue>5</issue><spage>1429</spage><epage>1433</epage><pages>1429-1433</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A versatile synthesis of the suitably functionalized pyrrolo[2,1-
f][1,2,4]triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1-
f][1,2,4]triazine template led to compounds with good in vitro potency against VEGFR-2 kinase. Glucuronidation of the phenol group is mitigated by incorporation of a basic amino group on the C-6 side chain of the pyrrolotriazine nucleus.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15713401</pmid><doi>10.1016/j.bmcl.2004.12.079</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2005-03, Vol.15 (5), p.1429-1433 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67430956 |
| source | ScienceDirect Freedom Collection |
| subjects | Angiogenesis Animals Antineoplastic agents Biological and medical sciences Cell Survival - drug effects Endothelium, Vascular - drug effects Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology General aspects Humans Kinase receptor Medical sciences Mice Microsomes, Liver - drug effects Microsomes, Liver - metabolism Models, Molecular Molecular Structure Pharmacology. Drug treatments Protein Binding SAR Structure-Activity Relationship Triazines - chemical synthesis Triazines - chemistry Triazines - pharmacology Vascular Endothelial Growth Factor Receptor-2 - antagonists & inhibitors VEGFR-2 |
| title | Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1- f][1,2,4]triazine based VEGFR-2 kinase inhibitors |
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