Hit to lead studies on (hetero)arylpyrimidines—Agonists of the canonical Wnt-β-catenin cellular messaging system
A series of (hetero)arylpyrimidines agonists of the Wnt-β-catenin cellular messaging system have been prepared. These compounds show activity in U2OS cells transfected with Wnt-3a, TCF-luciferase, Dkk-1 and tk-Renilla. Selected compounds show minimal GSK-3β inhibition indicating that the Wnt-β-caten...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010, Vol.20 (1), p.366-370 |
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| creator | Gilbert, Adam M. Bursavich, Matthew G. Alon, Nippa Bhat, Bheem M. Bex, Frederick J. Cain, Michael Coleburn, Valerie Gironda, Virginia Green, Paula Hauze, Diane B. Kharode, Yogendra Krishnamurthy, Girija Kirisits, Matthew Lam, Ho-Sun Liu, Yao-Bin Lombardi, Sabrina Matteo, Jeanne Murrills, Richard Robinson, John A. Selim, Sally Sharp, Michael Unwalla, Raymond Varadarajan, Usha Zhao, Weiguang Yaworsky, Paul J. |
| description | A series of (hetero)arylpyrimidines agonists of the Wnt-β-catenin cellular messaging system have been prepared. These compounds show activity in U2OS cells transfected with Wnt-3a, TCF-luciferase, Dkk-1 and tk-Renilla. Selected compounds show minimal GSK-3β inhibition indicating that the Wnt-β-catenin agonism activity most likely comes from interaction at Wnt-3a/Dkk-1. Two examples
1 and
25 show in vivo osteogenic activity in a mouse calvaria model. One example
1 is shown to activate non-phosphorylated β-catenin formation in bone. |
| doi_str_mv | 10.1016/j.bmcl.2009.10.093 |
| format | Article |
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1 and
25 show in vivo osteogenic activity in a mouse calvaria model. One example
1 is shown to activate non-phosphorylated β-catenin formation in bone.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2009.10.093</identifier><identifier>PMID: 19897365</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>(Hetero)arylpyrimidines ; Animals ; beta Catenin - agonists ; beta Catenin - metabolism ; Biological and medical sciences ; Bone Development - drug effects ; Bones, joints and connective tissue. Antiinflammatory agents ; Calvaria ; Cell Line, Tumor ; Glycogen Synthase Kinase 3 - metabolism ; Glycogen Synthase Kinase 3 beta ; Humans ; Imidazoles - chemical synthesis ; Imidazoles - chemistry ; Imidazoles - pharmacology ; Intercellular Signaling Peptides and Proteins - genetics ; Intercellular Signaling Peptides and Proteins - metabolism ; Medical sciences ; Mice ; Mice, Inbred C57BL ; Osteoporosis ; Pharmacology. Drug treatments ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrimidines - pharmacology ; Recombinant Fusion Proteins - agonists ; Recombinant Fusion Proteins - genetics ; Recombinant Fusion Proteins - metabolism ; Signal Transduction ; Skull - metabolism ; Wnt Proteins - agonists ; Wnt Proteins - genetics ; Wnt Proteins - metabolism ; Wnt-β-catenin agonist ; Wnt3 Protein ; Wnt3A Protein</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010, Vol.20 (1), p.366-370</ispartof><rights>2009 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright 2009 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-453f6d74c030f2998f861bf81efb930c55c334a2c44a46c22bce259c5a42bfa33</citedby><cites>FETCH-LOGICAL-c385t-453f6d74c030f2998f861bf81efb930c55c334a2c44a46c22bce259c5a42bfa33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X09015042$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,4010,27900,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22314261$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19897365$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gilbert, Adam M.</creatorcontrib><creatorcontrib>Bursavich, Matthew G.</creatorcontrib><creatorcontrib>Alon, Nippa</creatorcontrib><creatorcontrib>Bhat, Bheem M.</creatorcontrib><creatorcontrib>Bex, Frederick J.</creatorcontrib><creatorcontrib>Cain, Michael</creatorcontrib><creatorcontrib>Coleburn, Valerie</creatorcontrib><creatorcontrib>Gironda, Virginia</creatorcontrib><creatorcontrib>Green, Paula</creatorcontrib><creatorcontrib>Hauze, Diane B.</creatorcontrib><creatorcontrib>Kharode, Yogendra</creatorcontrib><creatorcontrib>Krishnamurthy, Girija</creatorcontrib><creatorcontrib>Kirisits, Matthew</creatorcontrib><creatorcontrib>Lam, Ho-Sun</creatorcontrib><creatorcontrib>Liu, Yao-Bin</creatorcontrib><creatorcontrib>Lombardi, Sabrina</creatorcontrib><creatorcontrib>Matteo, Jeanne</creatorcontrib><creatorcontrib>Murrills, Richard</creatorcontrib><creatorcontrib>Robinson, John A.</creatorcontrib><creatorcontrib>Selim, Sally</creatorcontrib><creatorcontrib>Sharp, Michael</creatorcontrib><creatorcontrib>Unwalla, Raymond</creatorcontrib><creatorcontrib>Varadarajan, Usha</creatorcontrib><creatorcontrib>Zhao, Weiguang</creatorcontrib><creatorcontrib>Yaworsky, Paul J.</creatorcontrib><title>Hit to lead studies on (hetero)arylpyrimidines—Agonists of the canonical Wnt-β-catenin cellular messaging system</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of (hetero)arylpyrimidines agonists of the Wnt-β-catenin cellular messaging system have been prepared. These compounds show activity in U2OS cells transfected with Wnt-3a, TCF-luciferase, Dkk-1 and tk-Renilla. Selected compounds show minimal GSK-3β inhibition indicating that the Wnt-β-catenin agonism activity most likely comes from interaction at Wnt-3a/Dkk-1. Two examples
1 and
25 show in vivo osteogenic activity in a mouse calvaria model. One example
1 is shown to activate non-phosphorylated β-catenin formation in bone.</description><subject>(Hetero)arylpyrimidines</subject><subject>Animals</subject><subject>beta Catenin - agonists</subject><subject>beta Catenin - metabolism</subject><subject>Biological and medical sciences</subject><subject>Bone Development - drug effects</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Calvaria</subject><subject>Cell Line, Tumor</subject><subject>Glycogen Synthase Kinase 3 - metabolism</subject><subject>Glycogen Synthase Kinase 3 beta</subject><subject>Humans</subject><subject>Imidazoles - chemical synthesis</subject><subject>Imidazoles - chemistry</subject><subject>Imidazoles - pharmacology</subject><subject>Intercellular Signaling Peptides and Proteins - genetics</subject><subject>Intercellular Signaling Peptides and Proteins - metabolism</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred C57BL</subject><subject>Osteoporosis</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - pharmacology</subject><subject>Recombinant Fusion Proteins - agonists</subject><subject>Recombinant Fusion Proteins - genetics</subject><subject>Recombinant Fusion Proteins - metabolism</subject><subject>Signal Transduction</subject><subject>Skull - metabolism</subject><subject>Wnt Proteins - agonists</subject><subject>Wnt Proteins - genetics</subject><subject>Wnt Proteins - metabolism</subject><subject>Wnt-β-catenin agonist</subject><subject>Wnt3 Protein</subject><subject>Wnt3A Protein</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>eNp9kM-KFDEQh4Mo7uzqC3iQXMT10GP-dU8H9rIs6goLXhS9hXS6MpuhOz2m0sLcfAifxAfxIXwS08ygN08FP75fUfUR8oyzNWe8eb1bd6Mb1oIxXYI10_IBWXHVqEoqVj8kK6YbVrVafTkj54g7xrhiSj0mZ1y3eiObekXwNmSaJzqA7SnmuQ-AdIr08h4ypOmVTYdhf0hhDH2IgL-__7jeTjFgLpSn-R6os7EEzg70c8zVr5-VsxliiNTBMMyDTXQERLsNcUvxgBnGJ-SRtwPC09O8IJ_evvl4c1vdfXj3_ub6rnKyrXOlaumbfqMck8wLrVvfNrzzLQffaclcXTsplRVOKasaJ0TnQNTa1VaJzlspL8jL4959mr7OgNmMAZerbIRpRrORUqu25qKQ4ki6NCEm8GZfXi6_G87M4trszOLaLK6XrLgupeen9XM3Qv-vcpJbgBcnwGLx45ONLuBfTgjJlWh44a6OHBQZ3wIkgy5AdNCHBC6bfgr_u-MP_SSgVQ</recordid><startdate>2010</startdate><enddate>2010</enddate><creator>Gilbert, Adam M.</creator><creator>Bursavich, Matthew G.</creator><creator>Alon, Nippa</creator><creator>Bhat, Bheem M.</creator><creator>Bex, Frederick J.</creator><creator>Cain, Michael</creator><creator>Coleburn, Valerie</creator><creator>Gironda, Virginia</creator><creator>Green, Paula</creator><creator>Hauze, Diane B.</creator><creator>Kharode, Yogendra</creator><creator>Krishnamurthy, Girija</creator><creator>Kirisits, Matthew</creator><creator>Lam, Ho-Sun</creator><creator>Liu, Yao-Bin</creator><creator>Lombardi, Sabrina</creator><creator>Matteo, Jeanne</creator><creator>Murrills, Richard</creator><creator>Robinson, John A.</creator><creator>Selim, Sally</creator><creator>Sharp, Michael</creator><creator>Unwalla, Raymond</creator><creator>Varadarajan, Usha</creator><creator>Zhao, Weiguang</creator><creator>Yaworsky, Paul J.</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>2010</creationdate><title>Hit to lead studies on (hetero)arylpyrimidines—Agonists of the canonical Wnt-β-catenin cellular messaging system</title><author>Gilbert, Adam M. ; Bursavich, Matthew G. ; Alon, Nippa ; Bhat, Bheem M. ; Bex, Frederick J. ; Cain, Michael ; Coleburn, Valerie ; Gironda, Virginia ; Green, Paula ; Hauze, Diane B. ; Kharode, Yogendra ; Krishnamurthy, Girija ; Kirisits, Matthew ; Lam, Ho-Sun ; Liu, Yao-Bin ; Lombardi, Sabrina ; Matteo, Jeanne ; Murrills, Richard ; Robinson, John A. ; Selim, Sally ; Sharp, Michael ; Unwalla, Raymond ; Varadarajan, Usha ; Zhao, Weiguang ; Yaworsky, Paul J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-453f6d74c030f2998f861bf81efb930c55c334a2c44a46c22bce259c5a42bfa33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>(Hetero)arylpyrimidines</topic><topic>Animals</topic><topic>beta Catenin - agonists</topic><topic>beta Catenin - metabolism</topic><topic>Biological and medical sciences</topic><topic>Bone Development - drug effects</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Calvaria</topic><topic>Cell Line, Tumor</topic><topic>Glycogen Synthase Kinase 3 - metabolism</topic><topic>Glycogen Synthase Kinase 3 beta</topic><topic>Humans</topic><topic>Imidazoles - chemical synthesis</topic><topic>Imidazoles - chemistry</topic><topic>Imidazoles - pharmacology</topic><topic>Intercellular Signaling Peptides and Proteins - genetics</topic><topic>Intercellular Signaling Peptides and Proteins - metabolism</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred C57BL</topic><topic>Osteoporosis</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - pharmacology</topic><topic>Recombinant Fusion Proteins - agonists</topic><topic>Recombinant Fusion Proteins - genetics</topic><topic>Recombinant Fusion Proteins - metabolism</topic><topic>Signal Transduction</topic><topic>Skull - metabolism</topic><topic>Wnt Proteins - agonists</topic><topic>Wnt Proteins - genetics</topic><topic>Wnt Proteins - metabolism</topic><topic>Wnt-β-catenin agonist</topic><topic>Wnt3 Protein</topic><topic>Wnt3A Protein</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gilbert, Adam M.</creatorcontrib><creatorcontrib>Bursavich, Matthew G.</creatorcontrib><creatorcontrib>Alon, Nippa</creatorcontrib><creatorcontrib>Bhat, Bheem M.</creatorcontrib><creatorcontrib>Bex, Frederick J.</creatorcontrib><creatorcontrib>Cain, Michael</creatorcontrib><creatorcontrib>Coleburn, Valerie</creatorcontrib><creatorcontrib>Gironda, Virginia</creatorcontrib><creatorcontrib>Green, Paula</creatorcontrib><creatorcontrib>Hauze, Diane B.</creatorcontrib><creatorcontrib>Kharode, Yogendra</creatorcontrib><creatorcontrib>Krishnamurthy, Girija</creatorcontrib><creatorcontrib>Kirisits, Matthew</creatorcontrib><creatorcontrib>Lam, Ho-Sun</creatorcontrib><creatorcontrib>Liu, Yao-Bin</creatorcontrib><creatorcontrib>Lombardi, Sabrina</creatorcontrib><creatorcontrib>Matteo, Jeanne</creatorcontrib><creatorcontrib>Murrills, Richard</creatorcontrib><creatorcontrib>Robinson, John A.</creatorcontrib><creatorcontrib>Selim, Sally</creatorcontrib><creatorcontrib>Sharp, Michael</creatorcontrib><creatorcontrib>Unwalla, Raymond</creatorcontrib><creatorcontrib>Varadarajan, Usha</creatorcontrib><creatorcontrib>Zhao, Weiguang</creatorcontrib><creatorcontrib>Yaworsky, Paul J.</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>Gilbert, Adam M.</au><au>Bursavich, Matthew G.</au><au>Alon, Nippa</au><au>Bhat, Bheem M.</au><au>Bex, Frederick J.</au><au>Cain, Michael</au><au>Coleburn, Valerie</au><au>Gironda, Virginia</au><au>Green, Paula</au><au>Hauze, Diane B.</au><au>Kharode, Yogendra</au><au>Krishnamurthy, Girija</au><au>Kirisits, Matthew</au><au>Lam, Ho-Sun</au><au>Liu, Yao-Bin</au><au>Lombardi, Sabrina</au><au>Matteo, Jeanne</au><au>Murrills, Richard</au><au>Robinson, John A.</au><au>Selim, Sally</au><au>Sharp, Michael</au><au>Unwalla, Raymond</au><au>Varadarajan, Usha</au><au>Zhao, Weiguang</au><au>Yaworsky, Paul J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hit to lead studies on (hetero)arylpyrimidines—Agonists of the canonical Wnt-β-catenin cellular messaging system</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010</date><risdate>2010</risdate><volume>20</volume><issue>1</issue><spage>366</spage><epage>370</epage><pages>366-370</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of (hetero)arylpyrimidines agonists of the Wnt-β-catenin cellular messaging system have been prepared. These compounds show activity in U2OS cells transfected with Wnt-3a, TCF-luciferase, Dkk-1 and tk-Renilla. Selected compounds show minimal GSK-3β inhibition indicating that the Wnt-β-catenin agonism activity most likely comes from interaction at Wnt-3a/Dkk-1. Two examples
1 and
25 show in vivo osteogenic activity in a mouse calvaria model. One example
1 is shown to activate non-phosphorylated β-catenin formation in bone.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19897365</pmid><doi>10.1016/j.bmcl.2009.10.093</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2010, Vol.20 (1), p.366-370 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | (Hetero)arylpyrimidines Animals beta Catenin - agonists beta Catenin - metabolism Biological and medical sciences Bone Development - drug effects Bones, joints and connective tissue. Antiinflammatory agents Calvaria Cell Line, Tumor Glycogen Synthase Kinase 3 - metabolism Glycogen Synthase Kinase 3 beta Humans Imidazoles - chemical synthesis Imidazoles - chemistry Imidazoles - pharmacology Intercellular Signaling Peptides and Proteins - genetics Intercellular Signaling Peptides and Proteins - metabolism Medical sciences Mice Mice, Inbred C57BL Osteoporosis Pharmacology. Drug treatments Pyrimidines - chemical synthesis Pyrimidines - chemistry Pyrimidines - pharmacology Recombinant Fusion Proteins - agonists Recombinant Fusion Proteins - genetics Recombinant Fusion Proteins - metabolism Signal Transduction Skull - metabolism Wnt Proteins - agonists Wnt Proteins - genetics Wnt Proteins - metabolism Wnt-β-catenin agonist Wnt3 Protein Wnt3A Protein |
| title | Hit to lead studies on (hetero)arylpyrimidines—Agonists of the canonical Wnt-β-catenin cellular messaging system |
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