Spirocyclopropyl β-Lactams as Mechanism-Based Inhibitors of Serine β-Lactamases. Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate Sulfone
Class A−class C mechanism-based β-lactamase inhibitors were designed on the basis of the intermediacy of an oxycarbenium species capable of cross-linking with amino acids residues in the active site. Penams 24 and 27 were very potent against AmpC in vitro. The MIC values of 24 in combination with pi...
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| Veröffentlicht in: | Journal of medicinal chemistry 2003-06, Vol.46 (13), p.2569-2571 |
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| container_end_page | 2571 |
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| container_issue | 13 |
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| container_title | Journal of medicinal chemistry |
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| creator | Sandanayaka, Vincent P Prashad, Amar S Yang, Youjun Williamson, R. Thomas Lin, Yang I Mansour, Tarek S |
| description | Class A−class C mechanism-based β-lactamase inhibitors were designed on the basis of the intermediacy of an oxycarbenium species capable of cross-linking with amino acids residues in the active site. Penams 24 and 27 were very potent against AmpC in vitro. The MIC values of 24 in combination with piperacillin against class A and class C producing organisms showed improvement over clinically used tazobactam. |
| doi_str_mv | 10.1021/jm034056q |
| format | Article |
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Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate Sulfone</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Sandanayaka, Vincent P ; Prashad, Amar S ; Yang, Youjun ; Williamson, R. Thomas ; Lin, Yang I ; Mansour, Tarek S</creator><creatorcontrib>Sandanayaka, Vincent P ; Prashad, Amar S ; Yang, Youjun ; Williamson, R. Thomas ; Lin, Yang I ; Mansour, Tarek S</creatorcontrib><description>Class A−class C mechanism-based β-lactamase inhibitors were designed on the basis of the intermediacy of an oxycarbenium species capable of cross-linking with amino acids residues in the active site. Penams 24 and 27 were very potent against AmpC in vitro. The MIC values of 24 in combination with piperacillin against class A and class C producing organisms showed improvement over clinically used tazobactam.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm034056q</identifier><identifier>PMID: 12801220</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. 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Drug treatments ; Pseudomonas aeruginosa - drug effects ; Rhodium ; Serine - chemistry ; Serratia marcescens - drug effects ; Spiro Compounds - chemical synthesis ; Spiro Compounds - chemistry ; Spiro Compounds - pharmacology ; Structure-Activity Relationship ; Sulbactam - analogs & derivatives ; Sulbactam - chemistry</subject><ispartof>Journal of medicinal chemistry, 2003-06, Vol.46 (13), p.2569-2571</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-c2e9fa430466025e6a7e8bec725255cdcf9a264e5277792fbc85ad10acea6b0b3</citedby><cites>FETCH-LOGICAL-a379t-c2e9fa430466025e6a7e8bec725255cdcf9a264e5277792fbc85ad10acea6b0b3</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/jm034056q$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm034056q$$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=14883421$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12801220$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sandanayaka, Vincent P</creatorcontrib><creatorcontrib>Prashad, Amar S</creatorcontrib><creatorcontrib>Yang, Youjun</creatorcontrib><creatorcontrib>Williamson, R. 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The MIC values of 24 in combination with piperacillin against class A and class C producing organisms showed improvement over clinically used tazobactam.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Bacterial Proteins</subject><subject>beta-Lactamase Inhibitors</subject><subject>beta-Lactamases - chemistry</subject><subject>beta-Lactams - chemical synthesis</subject><subject>beta-Lactams - chemistry</subject><subject>beta-Lactams - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Catalysis</subject><subject>Crystallography, X-Ray</subject><subject>Cyclopropanes - chemical synthesis</subject><subject>Cyclopropanes - chemistry</subject><subject>Cyclopropanes - pharmacology</subject><subject>Diazonium Compounds - chemistry</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Escherichia coli - drug effects</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Rhodium</subject><subject>Serine - chemistry</subject><subject>Serratia marcescens - drug effects</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Sulbactam - analogs & derivatives</subject><subject>Sulbactam - chemistry</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>eNptkUuO1DAQhiMEYpqBBRdA2YDEwoNTznMJGeYhNQKRZm1VnIraTWJn7EQicxyOwEHmTKTVzfSGVS3q81e__AfB64hfRByiD7uei5gn6d2TYBUlwFmc8_hpsOIcgEEK4ix44f2Ocy4iEM-DswhyHgHwVfC7GrSzaladHZwd5i58-MPWqEbsfYg-_EJqi0b7nn1CT014a7a61qN1PrRtWJHThk5PFsRfhNVsxi157cN6Dr9vbaOnnpU4YjffL4ry3zE0OGpr9qKUXWq8twMZrXTX7TcUVlPXWkMvg2ctdp5eHed58OPq86a8Yeuv17flxzVDkRUjU0BFi7HgcZpySCjFjPKaVAYJJIlqVFsgpDElkGVZAW2t8gSbiKMiTGtei_Pg3cG7ZLubyI-y117RPg3ZyctMCMhjXizg-wOonPXeUSsHp3t0s4y43BciHwtZ2DdH6VT31JzIYwML8PYIoFfYtQ6N0v7ExXkuYogWjh047Uf69bhH91OmmcgSuflWSbgpr9MCNvLy5EXl5c5Ozix_95-AfwGPorLZ</recordid><startdate>20030619</startdate><enddate>20030619</enddate><creator>Sandanayaka, Vincent P</creator><creator>Prashad, Amar S</creator><creator>Yang, Youjun</creator><creator>Williamson, R. 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Thomas ; Lin, Yang I ; Mansour, Tarek S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-c2e9fa430466025e6a7e8bec725255cdcf9a264e5277792fbc85ad10acea6b0b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Bacterial Proteins</topic><topic>beta-Lactamase Inhibitors</topic><topic>beta-Lactamases - chemistry</topic><topic>beta-Lactams - chemical synthesis</topic><topic>beta-Lactams - chemistry</topic><topic>beta-Lactams - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Catalysis</topic><topic>Crystallography, X-Ray</topic><topic>Cyclopropanes - chemical synthesis</topic><topic>Cyclopropanes - chemistry</topic><topic>Cyclopropanes - pharmacology</topic><topic>Diazonium Compounds - chemistry</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Escherichia coli - drug effects</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>Pseudomonas aeruginosa - drug effects</topic><topic>Rhodium</topic><topic>Serine - chemistry</topic><topic>Serratia marcescens - drug effects</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - chemistry</topic><topic>Spiro Compounds - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Sulbactam - analogs & derivatives</topic><topic>Sulbactam - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sandanayaka, Vincent P</creatorcontrib><creatorcontrib>Prashad, Amar S</creatorcontrib><creatorcontrib>Yang, Youjun</creatorcontrib><creatorcontrib>Williamson, R. 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Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate Sulfone</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2003-06-19</date><risdate>2003</risdate><volume>46</volume><issue>13</issue><spage>2569</spage><epage>2571</epage><pages>2569-2571</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Class A−class C mechanism-based β-lactamase inhibitors were designed on the basis of the intermediacy of an oxycarbenium species capable of cross-linking with amino acids residues in the active site. Penams 24 and 27 were very potent against AmpC in vitro. The MIC values of 24 in combination with piperacillin against class A and class C producing organisms showed improvement over clinically used tazobactam.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12801220</pmid><doi>10.1021/jm034056q</doi><tpages>3</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2003-06, Vol.46 (13), p.2569-2571 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Bacterial Proteins beta-Lactamase Inhibitors beta-Lactamases - chemistry beta-Lactams - chemical synthesis beta-Lactams - chemistry beta-Lactams - pharmacology Biological and medical sciences Catalysis Crystallography, X-Ray Cyclopropanes - chemical synthesis Cyclopropanes - chemistry Cyclopropanes - pharmacology Diazonium Compounds - chemistry Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Escherichia coli - drug effects Medical sciences Microbial Sensitivity Tests Models, Molecular Pharmacology. Drug treatments Pseudomonas aeruginosa - drug effects Rhodium Serine - chemistry Serratia marcescens - drug effects Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Spiro Compounds - pharmacology Structure-Activity Relationship Sulbactam - analogs & derivatives Sulbactam - chemistry |
| title | Spirocyclopropyl β-Lactams as Mechanism-Based Inhibitors of Serine β-Lactamases. Synthesis by Rhodium-Catalyzed Cyclopropanation of 6-Diazopenicillanate Sulfone |
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