5-((4-Aminopiperidin-1-yl)methyl)pyrrolotriazine dual inhibitors of EGFR and HER2 protein tyrosine kinases
5-((4-Aminopiperidin-1-yl)methyl)-pyrrolotriazine dual EGFR and HER2 protein tyrosine kinase inhibitor, 1c, exhibited potent kinase inhibition, antiproliferative activity, and good oral efficacy in EGFR/HER2 driven human tumor xenograft models. A broad range of potent pyrrolotriazine dual EGFR and H...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2007-09, Vol.17 (17), p.4947-4954 |
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| creator | Mastalerz, Harold Chang, Ming Chen, Ping Fink, Brian E. Gavai, Ashvinikumar Han, Wen-Ching Johnson, Walter Langley, David Lee, Francis Y. Leavitt, Kenneth Marathe, Punit Norris, Derek Oppenheimer, Simone Sleczka, Bogdan Tarrant, James Tokarski, John S. Vite, Gregory D. Vyas, Dolatrai M. Wong, Henry Wong, Tai W. Zhang, Hongjian Zhang, Guifen |
| description | 5-((4-Aminopiperidin-1-yl)methyl)-pyrrolotriazine dual EGFR and HER2 protein tyrosine kinase inhibitor,
1c, exhibited potent kinase inhibition, antiproliferative activity, and good oral efficacy in EGFR/HER2 driven human tumor xenograft models. A broad range of potent pyrrolotriazine dual EGFR and HER2 kinase inhibitors are possible with the C5 aminopiperidine solubilizing group.
Pyrrolotriazine dual EGFR/HER2 kinase inhibitors with a 5-((4-aminopiperidin-1-yl)methyl) solubilizing group were found to be superior to analogs with previously reported C-5 solubilizing groups. New synthetic methodology was developed for the parallel synthesis of C-4 analogs with the new solubilizing group. Interesting new leads were evaluated in tumor xenograft models and the C-4 aminofluorobenzylindazole,
1c, was found to exhibit the best antitumor activity. It is hypothesized that this solubilizing group extends into the ribose-phosphate portion of the ATP binding pocket and enhances the binding affinity of the inhibitor. |
| doi_str_mv | 10.1016/j.bmcl.2007.06.019 |
| format | Article |
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1c, exhibited potent kinase inhibition, antiproliferative activity, and good oral efficacy in EGFR/HER2 driven human tumor xenograft models. A broad range of potent pyrrolotriazine dual EGFR and HER2 kinase inhibitors are possible with the C5 aminopiperidine solubilizing group.
Pyrrolotriazine dual EGFR/HER2 kinase inhibitors with a 5-((4-aminopiperidin-1-yl)methyl) solubilizing group were found to be superior to analogs with previously reported C-5 solubilizing groups. New synthetic methodology was developed for the parallel synthesis of C-4 analogs with the new solubilizing group. Interesting new leads were evaluated in tumor xenograft models and the C-4 aminofluorobenzylindazole,
1c, was found to exhibit the best antitumor activity. It is hypothesized that this solubilizing group extends into the ribose-phosphate portion of the ATP binding pocket and enhances the binding affinity of the inhibitor.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2007.06.019</identifier><identifier>PMID: 17606372</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Adenosine Triphosphate - metabolism ; Animals ; Antineoplastic agents ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Chemistry, Pharmaceutical - methods ; Drug Design ; Drug Screening Assays, Antitumor ; EGFR ; General aspects ; HER2 ; Humans ; Inhibitory Concentration 50 ; Insecta ; Kinase inhibitor ; Medical sciences ; Models, Chemical ; Neoplasm Transplantation ; Neoplasms - drug therapy ; Pharmacology. Drug treatments ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Piperidines - pharmacology ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Pyrroles - pharmacology ; Pyrrolotriazine ; Receptor, Epidermal Growth Factor - chemistry ; Receptor, ErbB-2 - chemistry ; Triazines - chemical synthesis ; Triazines - chemistry ; Triazines - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2007-09, Vol.17 (17), p.4947-4954</ispartof><rights>2007 Elsevier Ltd</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-5fb5b4cccac9c5e22459c2a4015fcfa8f46a0896a61934c9e6f24c3b53429f9c3</citedby><cites>FETCH-LOGICAL-c415t-5fb5b4cccac9c5e22459c2a4015fcfa8f46a0896a61934c9e6f24c3b53429f9c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X07007007$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18993876$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17606372$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mastalerz, Harold</creatorcontrib><creatorcontrib>Chang, Ming</creatorcontrib><creatorcontrib>Chen, Ping</creatorcontrib><creatorcontrib>Fink, Brian E.</creatorcontrib><creatorcontrib>Gavai, Ashvinikumar</creatorcontrib><creatorcontrib>Han, Wen-Ching</creatorcontrib><creatorcontrib>Johnson, Walter</creatorcontrib><creatorcontrib>Langley, David</creatorcontrib><creatorcontrib>Lee, Francis Y.</creatorcontrib><creatorcontrib>Leavitt, Kenneth</creatorcontrib><creatorcontrib>Marathe, Punit</creatorcontrib><creatorcontrib>Norris, Derek</creatorcontrib><creatorcontrib>Oppenheimer, Simone</creatorcontrib><creatorcontrib>Sleczka, Bogdan</creatorcontrib><creatorcontrib>Tarrant, James</creatorcontrib><creatorcontrib>Tokarski, John S.</creatorcontrib><creatorcontrib>Vite, Gregory D.</creatorcontrib><creatorcontrib>Vyas, Dolatrai M.</creatorcontrib><creatorcontrib>Wong, Henry</creatorcontrib><creatorcontrib>Wong, Tai W.</creatorcontrib><creatorcontrib>Zhang, Hongjian</creatorcontrib><creatorcontrib>Zhang, Guifen</creatorcontrib><title>5-((4-Aminopiperidin-1-yl)methyl)pyrrolotriazine dual inhibitors of EGFR and HER2 protein tyrosine kinases</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>5-((4-Aminopiperidin-1-yl)methyl)-pyrrolotriazine dual EGFR and HER2 protein tyrosine kinase inhibitor,
1c, exhibited potent kinase inhibition, antiproliferative activity, and good oral efficacy in EGFR/HER2 driven human tumor xenograft models. A broad range of potent pyrrolotriazine dual EGFR and HER2 kinase inhibitors are possible with the C5 aminopiperidine solubilizing group.
Pyrrolotriazine dual EGFR/HER2 kinase inhibitors with a 5-((4-aminopiperidin-1-yl)methyl) solubilizing group were found to be superior to analogs with previously reported C-5 solubilizing groups. New synthetic methodology was developed for the parallel synthesis of C-4 analogs with the new solubilizing group. Interesting new leads were evaluated in tumor xenograft models and the C-4 aminofluorobenzylindazole,
1c, was found to exhibit the best antitumor activity. It is hypothesized that this solubilizing group extends into the ribose-phosphate portion of the ATP binding pocket and enhances the binding affinity of the inhibitor.</description><subject>Adenosine Triphosphate - metabolism</subject><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Chemistry, Pharmaceutical - methods</subject><subject>Drug Design</subject><subject>Drug Screening Assays, Antitumor</subject><subject>EGFR</subject><subject>General aspects</subject><subject>HER2</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Insecta</subject><subject>Kinase inhibitor</subject><subject>Medical sciences</subject><subject>Models, Chemical</subject><subject>Neoplasm Transplantation</subject><subject>Neoplasms - drug therapy</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Pyrroles - pharmacology</subject><subject>Pyrrolotriazine</subject><subject>Receptor, Epidermal Growth Factor - chemistry</subject><subject>Receptor, ErbB-2 - chemistry</subject><subject>Triazines - chemical synthesis</subject><subject>Triazines - chemistry</subject><subject>Triazines - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFq3DAURUVpaaZJf6CL4k1DspAr2ZJsQTchTJJCoBAa6E7Iz09EU1tyJU9h8vX1ZAay6-ptzr3vcgj5xFnJGVdfN2U3wlBWjDUlUyXj-g1ZcaEErQWTb8mKacVoq8WvE_Ih5w1jXDAh3pMT3iim6qZakY2kFxeCXo0-xMlPmHzvA-V0N1yOOD8tZ9qlFIc4J2-ffcCi39qh8OHJd36OKRfRFevbm4fChr64Wz9UxZTijD4U8y7FvE_89sFmzGfknbNDxo_He0oeb9Y_r-_o_Y_b79dX9xQElzOVrpOdAAALGiRWlZAaKisYlw6cbZ1QlrVaWcV1LUCjcpWAupO1qLTTUJ-S80PvMuTPFvNsRp8Bh8EGjNtsuJZcNo1awOoAwjI0J3RmSn60aWc4M3vDZmP2hs3esGHKLIaX0Odj-7YbsX-NHJUuwJcjYDPYwSUbwOdXrtW6bl--fztwuLj46zGZDB4DYO8Twmz66P-34x-IkJnr</recordid><startdate>20070901</startdate><enddate>20070901</enddate><creator>Mastalerz, Harold</creator><creator>Chang, Ming</creator><creator>Chen, Ping</creator><creator>Fink, Brian E.</creator><creator>Gavai, Ashvinikumar</creator><creator>Han, Wen-Ching</creator><creator>Johnson, Walter</creator><creator>Langley, David</creator><creator>Lee, Francis Y.</creator><creator>Leavitt, Kenneth</creator><creator>Marathe, Punit</creator><creator>Norris, Derek</creator><creator>Oppenheimer, Simone</creator><creator>Sleczka, Bogdan</creator><creator>Tarrant, James</creator><creator>Tokarski, John S.</creator><creator>Vite, Gregory D.</creator><creator>Vyas, Dolatrai M.</creator><creator>Wong, Henry</creator><creator>Wong, Tai W.</creator><creator>Zhang, Hongjian</creator><creator>Zhang, Guifen</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></search><sort><creationdate>20070901</creationdate><title>5-((4-Aminopiperidin-1-yl)methyl)pyrrolotriazine dual inhibitors of EGFR and HER2 protein tyrosine kinases</title><author>Mastalerz, Harold ; Chang, Ming ; Chen, Ping ; Fink, Brian E. ; Gavai, Ashvinikumar ; Han, Wen-Ching ; Johnson, Walter ; Langley, David ; Lee, Francis Y. ; Leavitt, Kenneth ; Marathe, Punit ; Norris, Derek ; Oppenheimer, Simone ; Sleczka, Bogdan ; Tarrant, James ; Tokarski, John S. ; Vite, Gregory D. ; Vyas, Dolatrai M. ; Wong, Henry ; Wong, Tai W. ; Zhang, Hongjian ; Zhang, Guifen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-5fb5b4cccac9c5e22459c2a4015fcfa8f46a0896a61934c9e6f24c3b53429f9c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Adenosine Triphosphate - metabolism</topic><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Chemistry, Pharmaceutical - methods</topic><topic>Drug Design</topic><topic>Drug Screening Assays, Antitumor</topic><topic>EGFR</topic><topic>General aspects</topic><topic>HER2</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Insecta</topic><topic>Kinase inhibitor</topic><topic>Medical sciences</topic><topic>Models, Chemical</topic><topic>Neoplasm Transplantation</topic><topic>Neoplasms - drug therapy</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Pyrroles - pharmacology</topic><topic>Pyrrolotriazine</topic><topic>Receptor, Epidermal Growth Factor - chemistry</topic><topic>Receptor, ErbB-2 - chemistry</topic><topic>Triazines - chemical synthesis</topic><topic>Triazines - chemistry</topic><topic>Triazines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mastalerz, Harold</creatorcontrib><creatorcontrib>Chang, Ming</creatorcontrib><creatorcontrib>Chen, Ping</creatorcontrib><creatorcontrib>Fink, Brian E.</creatorcontrib><creatorcontrib>Gavai, Ashvinikumar</creatorcontrib><creatorcontrib>Han, Wen-Ching</creatorcontrib><creatorcontrib>Johnson, Walter</creatorcontrib><creatorcontrib>Langley, David</creatorcontrib><creatorcontrib>Lee, Francis Y.</creatorcontrib><creatorcontrib>Leavitt, Kenneth</creatorcontrib><creatorcontrib>Marathe, Punit</creatorcontrib><creatorcontrib>Norris, Derek</creatorcontrib><creatorcontrib>Oppenheimer, Simone</creatorcontrib><creatorcontrib>Sleczka, Bogdan</creatorcontrib><creatorcontrib>Tarrant, James</creatorcontrib><creatorcontrib>Tokarski, John S.</creatorcontrib><creatorcontrib>Vite, Gregory D.</creatorcontrib><creatorcontrib>Vyas, Dolatrai M.</creatorcontrib><creatorcontrib>Wong, Henry</creatorcontrib><creatorcontrib>Wong, Tai W.</creatorcontrib><creatorcontrib>Zhang, Hongjian</creatorcontrib><creatorcontrib>Zhang, Guifen</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><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mastalerz, Harold</au><au>Chang, Ming</au><au>Chen, Ping</au><au>Fink, Brian E.</au><au>Gavai, Ashvinikumar</au><au>Han, Wen-Ching</au><au>Johnson, Walter</au><au>Langley, David</au><au>Lee, Francis Y.</au><au>Leavitt, Kenneth</au><au>Marathe, Punit</au><au>Norris, Derek</au><au>Oppenheimer, Simone</au><au>Sleczka, Bogdan</au><au>Tarrant, James</au><au>Tokarski, John S.</au><au>Vite, Gregory D.</au><au>Vyas, Dolatrai M.</au><au>Wong, Henry</au><au>Wong, Tai W.</au><au>Zhang, Hongjian</au><au>Zhang, Guifen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>5-((4-Aminopiperidin-1-yl)methyl)pyrrolotriazine dual inhibitors of EGFR and HER2 protein tyrosine kinases</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2007-09-01</date><risdate>2007</risdate><volume>17</volume><issue>17</issue><spage>4947</spage><epage>4954</epage><pages>4947-4954</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>5-((4-Aminopiperidin-1-yl)methyl)-pyrrolotriazine dual EGFR and HER2 protein tyrosine kinase inhibitor,
1c, exhibited potent kinase inhibition, antiproliferative activity, and good oral efficacy in EGFR/HER2 driven human tumor xenograft models. A broad range of potent pyrrolotriazine dual EGFR and HER2 kinase inhibitors are possible with the C5 aminopiperidine solubilizing group.
Pyrrolotriazine dual EGFR/HER2 kinase inhibitors with a 5-((4-aminopiperidin-1-yl)methyl) solubilizing group were found to be superior to analogs with previously reported C-5 solubilizing groups. New synthetic methodology was developed for the parallel synthesis of C-4 analogs with the new solubilizing group. Interesting new leads were evaluated in tumor xenograft models and the C-4 aminofluorobenzylindazole,
1c, was found to exhibit the best antitumor activity. It is hypothesized that this solubilizing group extends into the ribose-phosphate portion of the ATP binding pocket and enhances the binding affinity of the inhibitor.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17606372</pmid><doi>10.1016/j.bmcl.2007.06.019</doi><tpages>8</tpages></addata></record> |
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| subjects | Adenosine Triphosphate - metabolism Animals Antineoplastic agents Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Chemistry, Pharmaceutical - methods Drug Design Drug Screening Assays, Antitumor EGFR General aspects HER2 Humans Inhibitory Concentration 50 Insecta Kinase inhibitor Medical sciences Models, Chemical Neoplasm Transplantation Neoplasms - drug therapy Pharmacology. Drug treatments Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Pyrroles - chemical synthesis Pyrroles - chemistry Pyrroles - pharmacology Pyrrolotriazine Receptor, Epidermal Growth Factor - chemistry Receptor, ErbB-2 - chemistry Triazines - chemical synthesis Triazines - chemistry Triazines - pharmacology |
| title | 5-((4-Aminopiperidin-1-yl)methyl)pyrrolotriazine dual inhibitors of EGFR and HER2 protein tyrosine kinases |
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