Glycosylated dihydrochalcones as potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitors
A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2. A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2. The core structure was derived from compound 1a. Modification of the benzofuran moiety and 4′-substituent of the p...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2004-10, Vol.14 (20), p.5121-5125 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Dudash, Joseph Zhang, Xiaoyan Zeck, Roxanne E. Johnson, Sigmond G. Cox, Geoffrey G. Conway, Bruce R. Rybczynski, Philip J. Demarest, Keith T. |
| description | A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2.
A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2. The core structure was derived from compound 1a. Modification of the benzofuran moiety and 4′-substituent of the phenyl ring in compound 1a improved selectivity at SGLT2. Select compounds were compared to 1a in metabolic stability and in vivo efficacy studies. |
| doi_str_mv | 10.1016/j.bmcl.2004.07.082 |
| format | Article |
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A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2. The core structure was derived from compound 1a. Modification of the benzofuran moiety and 4′-substituent of the phenyl ring in compound 1a improved selectivity at SGLT2. Select compounds were compared to 1a in metabolic stability and in vivo efficacy studies.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2004.07.082</identifier><identifier>PMID: 15380212</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Biological and medical sciences ; Cells, Cultured ; Chalcone - analogs & derivatives ; Chalcone - chemical synthesis ; Chalcone - pharmacology ; Chalcones ; Drug Stability ; Glycosylation ; Humans ; In Vitro Techniques ; Male ; Medical sciences ; Membrane Glycoproteins - antagonists & inhibitors ; Microsomes, Liver - metabolism ; Miscellaneous ; Monosaccharide Transport Proteins - antagonists & inhibitors ; Pharmacology. Drug treatments ; Phlorhizin - chemical synthesis ; Phlorhizin - pharmacology ; Rats ; Rats, Zucker ; Sodium-Glucose Transporter 1 ; Sodium-Glucose Transporter 2 ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2004-10, Vol.14 (20), p.5121-5125</ispartof><rights>2004 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c382t-e4eaa934432dc38e9dbdfbfd30db47fee830409ce3f4667be918855264f02db03</citedby><cites>FETCH-LOGICAL-c382t-e4eaa934432dc38e9dbdfbfd30db47fee830409ce3f4667be918855264f02db03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X0400976X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16119660$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15380212$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dudash, Joseph</creatorcontrib><creatorcontrib>Zhang, Xiaoyan</creatorcontrib><creatorcontrib>Zeck, Roxanne E.</creatorcontrib><creatorcontrib>Johnson, Sigmond G.</creatorcontrib><creatorcontrib>Cox, Geoffrey G.</creatorcontrib><creatorcontrib>Conway, Bruce R.</creatorcontrib><creatorcontrib>Rybczynski, Philip J.</creatorcontrib><creatorcontrib>Demarest, Keith T.</creatorcontrib><title>Glycosylated dihydrochalcones as potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2.
A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2. The core structure was derived from compound 1a. Modification of the benzofuran moiety and 4′-substituent of the phenyl ring in compound 1a improved selectivity at SGLT2. Select compounds were compared to 1a in metabolic stability and in vivo efficacy studies.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cells, Cultured</subject><subject>Chalcone - analogs & derivatives</subject><subject>Chalcone - chemical synthesis</subject><subject>Chalcone - pharmacology</subject><subject>Chalcones</subject><subject>Drug Stability</subject><subject>Glycosylation</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Membrane Glycoproteins - antagonists & inhibitors</subject><subject>Microsomes, Liver - metabolism</subject><subject>Miscellaneous</subject><subject>Monosaccharide Transport Proteins - antagonists & inhibitors</subject><subject>Pharmacology. Drug treatments</subject><subject>Phlorhizin - chemical synthesis</subject><subject>Phlorhizin - pharmacology</subject><subject>Rats</subject><subject>Rats, Zucker</subject><subject>Sodium-Glucose Transporter 1</subject><subject>Sodium-Glucose Transporter 2</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2r1DAUhoMo3vHqH3Ah2Si6aD35aNqAG7noKAy48AruQpqcOhnSZkzaC_Pv7TADd-fqwOF5X14eQl4zqBkw9fFQ96OLNQeQNbQ1dPwJ2TCpZCUkNE_JBrSCqtPy9w15UcoBgEmQ8jm5YY3ogDO-IfttPLlUTtHO6KkP-5PPye1tdGnCQm2hxzTjNFM7eVowopvDA9KSfFhG-icuaxipS9Wc7VSOKc-YKafvf2539_wDDdM-9GFOubwkzwYbC7663lvy6-uX-7tv1e7H9vvd513lRMfnCiVaq4WUgvv1g9r3fugHL8D3sh0QOwEStEMxSKXaHjXruqbhSg7AfQ_ilry79B5z-rtgmc0YisMY7YRpKUapTje65SvIL6DLqZSMgznmMNp8MgzM2a85mLNfc_ZroDWr3zX05tq-9CP6x8hV6Aq8vQK2OBuH1YoL5ZFTjGmlzjM_XThcXTwEzKa4gJNDH_Lq2PgU_rfjH4fhmn4</recordid><startdate>20041018</startdate><enddate>20041018</enddate><creator>Dudash, Joseph</creator><creator>Zhang, Xiaoyan</creator><creator>Zeck, Roxanne E.</creator><creator>Johnson, Sigmond G.</creator><creator>Cox, Geoffrey G.</creator><creator>Conway, Bruce R.</creator><creator>Rybczynski, Philip J.</creator><creator>Demarest, Keith T.</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>20041018</creationdate><title>Glycosylated dihydrochalcones as potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitors</title><author>Dudash, Joseph ; Zhang, Xiaoyan ; Zeck, Roxanne E. ; Johnson, Sigmond G. ; Cox, Geoffrey G. ; Conway, Bruce R. ; Rybczynski, Philip J. ; Demarest, Keith T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c382t-e4eaa934432dc38e9dbdfbfd30db47fee830409ce3f4667be918855264f02db03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cells, Cultured</topic><topic>Chalcone - analogs & derivatives</topic><topic>Chalcone - chemical synthesis</topic><topic>Chalcone - pharmacology</topic><topic>Chalcones</topic><topic>Drug Stability</topic><topic>Glycosylation</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Membrane Glycoproteins - antagonists & inhibitors</topic><topic>Microsomes, Liver - metabolism</topic><topic>Miscellaneous</topic><topic>Monosaccharide Transport Proteins - antagonists & inhibitors</topic><topic>Pharmacology. Drug treatments</topic><topic>Phlorhizin - chemical synthesis</topic><topic>Phlorhizin - pharmacology</topic><topic>Rats</topic><topic>Rats, Zucker</topic><topic>Sodium-Glucose Transporter 1</topic><topic>Sodium-Glucose Transporter 2</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dudash, Joseph</creatorcontrib><creatorcontrib>Zhang, Xiaoyan</creatorcontrib><creatorcontrib>Zeck, Roxanne E.</creatorcontrib><creatorcontrib>Johnson, Sigmond G.</creatorcontrib><creatorcontrib>Cox, Geoffrey G.</creatorcontrib><creatorcontrib>Conway, Bruce R.</creatorcontrib><creatorcontrib>Rybczynski, Philip J.</creatorcontrib><creatorcontrib>Demarest, Keith T.</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>Dudash, Joseph</au><au>Zhang, Xiaoyan</au><au>Zeck, Roxanne E.</au><au>Johnson, Sigmond G.</au><au>Cox, Geoffrey G.</au><au>Conway, Bruce R.</au><au>Rybczynski, Philip J.</au><au>Demarest, Keith T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Glycosylated dihydrochalcones as potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2004-10-18</date><risdate>2004</risdate><volume>14</volume><issue>20</issue><spage>5121</spage><epage>5125</epage><pages>5121-5125</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2.
A series of glucose conjugates was synthesized and tested for inhibition of SGLT1 and SGLT2. The core structure was derived from compound 1a. Modification of the benzofuran moiety and 4′-substituent of the phenyl ring in compound 1a improved selectivity at SGLT2. Select compounds were compared to 1a in metabolic stability and in vivo efficacy studies.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15380212</pmid><doi>10.1016/j.bmcl.2004.07.082</doi><tpages>5</tpages></addata></record> |
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| subjects | Animals Biological and medical sciences Cells, Cultured Chalcone - analogs & derivatives Chalcone - chemical synthesis Chalcone - pharmacology Chalcones Drug Stability Glycosylation Humans In Vitro Techniques Male Medical sciences Membrane Glycoproteins - antagonists & inhibitors Microsomes, Liver - metabolism Miscellaneous Monosaccharide Transport Proteins - antagonists & inhibitors Pharmacology. Drug treatments Phlorhizin - chemical synthesis Phlorhizin - pharmacology Rats Rats, Zucker Sodium-Glucose Transporter 1 Sodium-Glucose Transporter 2 Structure-Activity Relationship |
| title | Glycosylated dihydrochalcones as potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitors |
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