5,6,7-Trisubstituted 4-Aminopyrido[2,3-d]pyrimidines as Novel Inhibitors of Adenosine Kinase
The synthesis and structure−activity relationship of a series of 5,6,7-trisubstituted 4-aminopyrido[2,3-d]pyrimidines as novel nonnucleoside adenosine kinase inhibitors is described. A variety of alkyl, aryl, and heteroaryl substituents were found to be tolerated at the C5, C6, and C7 positions of t...
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| Veröffentlicht in: | Journal of medicinal chemistry 2003-11, Vol.46 (24), p.5249-5257 |
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| container_issue | 24 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 46 |
| creator | Perner, Richard J Gu, Yu-Gui Lee, Chih-Hung Bayburt, Erol K McKie, Jeffery Alexander, Karen M Kohlhaas, Kathy L Wismer, Carol T Mikusa, Joe Jarvis, Michael F Kowaluk, Elizabeth A Bhagwat, Shripad S |
| description | The synthesis and structure−activity relationship of a series of 5,6,7-trisubstituted 4-aminopyrido[2,3-d]pyrimidines as novel nonnucleoside adenosine kinase inhibitors is described. A variety of alkyl, aryl, and heteroaryl substituents were found to be tolerated at the C5, C6, and C7 positions of the pyridopyrimidine core. These studies have led to the identification of analogues that are potent inhibitors of adenosine kinase with in vivo analgesic activity. |
| doi_str_mv | 10.1021/jm030327l |
| format | Article |
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A variety of alkyl, aryl, and heteroaryl substituents were found to be tolerated at the C5, C6, and C7 positions of the pyridopyrimidine core. These studies have led to the identification of analogues that are potent inhibitors of adenosine kinase with in vivo analgesic activity.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm030327l</identifier><identifier>PMID: 14613327</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Adenosine Kinase - antagonists & inhibitors ; Adenosine Kinase - chemistry ; Analgesics ; Analgesics - chemical synthesis ; Analgesics - chemistry ; Analgesics - pharmacology ; Animals ; Biological and medical sciences ; Cell Line, Tumor ; Humans ; Medical sciences ; Mice ; Miscellaneous ; Neuropharmacology ; Pain Measurement ; Pharmacology. Drug treatments ; Phosphorylation ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyridines - pharmacology ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrimidines - pharmacology ; Rats ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2003-11, Vol.46 (24), p.5249-5257</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-a7f7cc082193359bd41b6f2dc64e58578c8a28b5f5f99bd2f7312ff2cba9e3823</citedby><cites>FETCH-LOGICAL-a379t-a7f7cc082193359bd41b6f2dc64e58578c8a28b5f5f99bd2f7312ff2cba9e3823</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm030327l$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm030327l$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15292869$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14613327$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Perner, Richard J</creatorcontrib><creatorcontrib>Gu, Yu-Gui</creatorcontrib><creatorcontrib>Lee, Chih-Hung</creatorcontrib><creatorcontrib>Bayburt, Erol K</creatorcontrib><creatorcontrib>McKie, Jeffery</creatorcontrib><creatorcontrib>Alexander, Karen M</creatorcontrib><creatorcontrib>Kohlhaas, Kathy L</creatorcontrib><creatorcontrib>Wismer, Carol T</creatorcontrib><creatorcontrib>Mikusa, Joe</creatorcontrib><creatorcontrib>Jarvis, Michael F</creatorcontrib><creatorcontrib>Kowaluk, Elizabeth A</creatorcontrib><creatorcontrib>Bhagwat, Shripad S</creatorcontrib><title>5,6,7-Trisubstituted 4-Aminopyrido[2,3-d]pyrimidines as Novel Inhibitors of Adenosine Kinase</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The synthesis and structure−activity relationship of a series of 5,6,7-trisubstituted 4-aminopyrido[2,3-d]pyrimidines as novel nonnucleoside adenosine kinase inhibitors is described. A variety of alkyl, aryl, and heteroaryl substituents were found to be tolerated at the C5, C6, and C7 positions of the pyridopyrimidine core. These studies have led to the identification of analogues that are potent inhibitors of adenosine kinase with in vivo analgesic activity.</description><subject>Adenosine Kinase - antagonists & inhibitors</subject><subject>Adenosine Kinase - chemistry</subject><subject>Analgesics</subject><subject>Analgesics - chemical synthesis</subject><subject>Analgesics - chemistry</subject><subject>Analgesics - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Miscellaneous</subject><subject>Neuropharmacology</subject><subject>Pain Measurement</subject><subject>Pharmacology. Drug treatments</subject><subject>Phosphorylation</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - pharmacology</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - pharmacology</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE9r3DAQxUVoabZpD_0CwZcECqtWfy37uISmCQlNSLcQaIuQZYloY1tbjV2abx8tu2QvPQ3D_ObNvIfQB0o-UcLo51VPOOFMdQdoRiUjWFREvEIzQhjDrGT8EL0FWBFCOGX8DTqkoqQ8L8zQLzkv5wovU4CpgTGM0-jaQuBFH4a4fkqhjT_ZnOP296bpQxsGB4WB4lv867ricngITRhjgiL6YtG6IUImiqswGHDv0GtvOnDvd_UI_Tj_sjy7wNc3Xy_PFtfYcFWP2CivrCUVozXnsm5aQZvSs9aWwslKqspWhlWN9NLXecq8yja8Z7YxteMV40fodKu7TvHP5GDUfQDrus4MLk6gFeWK1qLO4MctaFMESM7rdTZl0pOmRG-i1C9RZvZ4Jzo1vWv35C67DJzsAAPWdD6ZwQbYc5LVrCo3R_GWCzC6fy9zkx51qbiSenn7XQt6f3cl7qQ-3-saC3oVpzTk7P7z4DMBuJWp</recordid><startdate>20031120</startdate><enddate>20031120</enddate><creator>Perner, Richard J</creator><creator>Gu, Yu-Gui</creator><creator>Lee, Chih-Hung</creator><creator>Bayburt, Erol K</creator><creator>McKie, Jeffery</creator><creator>Alexander, Karen M</creator><creator>Kohlhaas, Kathy L</creator><creator>Wismer, Carol T</creator><creator>Mikusa, Joe</creator><creator>Jarvis, Michael F</creator><creator>Kowaluk, Elizabeth A</creator><creator>Bhagwat, Shripad S</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20031120</creationdate><title>5,6,7-Trisubstituted 4-Aminopyrido[2,3-d]pyrimidines as Novel Inhibitors of Adenosine Kinase</title><author>Perner, Richard J ; Gu, Yu-Gui ; Lee, Chih-Hung ; Bayburt, Erol K ; McKie, Jeffery ; Alexander, Karen M ; Kohlhaas, Kathy L ; Wismer, Carol T ; Mikusa, Joe ; Jarvis, Michael F ; Kowaluk, Elizabeth A ; Bhagwat, Shripad S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-a7f7cc082193359bd41b6f2dc64e58578c8a28b5f5f99bd2f7312ff2cba9e3823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Adenosine Kinase - antagonists & inhibitors</topic><topic>Adenosine Kinase - chemistry</topic><topic>Analgesics</topic><topic>Analgesics - chemical synthesis</topic><topic>Analgesics - chemistry</topic><topic>Analgesics - pharmacology</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Miscellaneous</topic><topic>Neuropharmacology</topic><topic>Pain Measurement</topic><topic>Pharmacology. Drug treatments</topic><topic>Phosphorylation</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - pharmacology</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - pharmacology</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Perner, Richard J</creatorcontrib><creatorcontrib>Gu, Yu-Gui</creatorcontrib><creatorcontrib>Lee, Chih-Hung</creatorcontrib><creatorcontrib>Bayburt, Erol K</creatorcontrib><creatorcontrib>McKie, Jeffery</creatorcontrib><creatorcontrib>Alexander, Karen M</creatorcontrib><creatorcontrib>Kohlhaas, Kathy L</creatorcontrib><creatorcontrib>Wismer, Carol T</creatorcontrib><creatorcontrib>Mikusa, Joe</creatorcontrib><creatorcontrib>Jarvis, Michael F</creatorcontrib><creatorcontrib>Kowaluk, Elizabeth A</creatorcontrib><creatorcontrib>Bhagwat, Shripad S</creatorcontrib><collection>Istex</collection><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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Perner, Richard J</au><au>Gu, Yu-Gui</au><au>Lee, Chih-Hung</au><au>Bayburt, Erol K</au><au>McKie, Jeffery</au><au>Alexander, Karen M</au><au>Kohlhaas, Kathy L</au><au>Wismer, Carol T</au><au>Mikusa, Joe</au><au>Jarvis, Michael F</au><au>Kowaluk, Elizabeth A</au><au>Bhagwat, Shripad S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>5,6,7-Trisubstituted 4-Aminopyrido[2,3-d]pyrimidines as Novel Inhibitors of Adenosine Kinase</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2003-11-20</date><risdate>2003</risdate><volume>46</volume><issue>24</issue><spage>5249</spage><epage>5257</epage><pages>5249-5257</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The synthesis and structure−activity relationship of a series of 5,6,7-trisubstituted 4-aminopyrido[2,3-d]pyrimidines as novel nonnucleoside adenosine kinase inhibitors is described. A variety of alkyl, aryl, and heteroaryl substituents were found to be tolerated at the C5, C6, and C7 positions of the pyridopyrimidine core. These studies have led to the identification of analogues that are potent inhibitors of adenosine kinase with in vivo analgesic activity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14613327</pmid><doi>10.1021/jm030327l</doi><tpages>9</tpages></addata></record> |
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| subjects | Adenosine Kinase - antagonists & inhibitors Adenosine Kinase - chemistry Analgesics Analgesics - chemical synthesis Analgesics - chemistry Analgesics - pharmacology Animals Biological and medical sciences Cell Line, Tumor Humans Medical sciences Mice Miscellaneous Neuropharmacology Pain Measurement Pharmacology. Drug treatments Phosphorylation Pyridines - chemical synthesis Pyridines - chemistry Pyridines - pharmacology Pyrimidines - chemical synthesis Pyrimidines - chemistry Pyrimidines - pharmacology Rats Structure-Activity Relationship |
| title | 5,6,7-Trisubstituted 4-Aminopyrido[2,3-d]pyrimidines as Novel Inhibitors of Adenosine Kinase |
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