Synthesis and biological evaluation of novel 1β-methylcarbapenems with isothiazoloethenyl side chains
The synthesis of novel 1β-methylcarbapenems 1a, b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2003-02, Vol.13 (3), p.463-466 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Kang, Yong Koo Lee, Kyung Seok Yoo, Kyung Ho Shin, Kye Jung Kim, Dong Chan Lee, Chang-Seok Kong, Jae Yang Kim, Dong Jin |
| description | The synthesis of novel 1β-methylcarbapenems
1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem.
The synthesis of novel 1β-methylcarbapenems
1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem. |
| doi_str_mv | 10.1016/S0960-894X(02)00948-4 |
| format | Article |
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1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem.
The synthesis of novel 1β-methylcarbapenems
1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(02)00948-4</identifier><identifier>PMID: 12565951</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - pharmacokinetics ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Bacteria - drug effects ; Biological and medical sciences ; Carbapenems - chemical synthesis ; Carbapenems - pharmacokinetics ; Carbapenems - pharmacology ; Half-Life ; Indicators and Reagents ; Medical sciences ; Meropenem ; Mice ; Microbial Sensitivity Tests ; Oxidation-Reduction ; Pharmacology. Drug treatments ; Rats ; Structure-Activity Relationship ; Thienamycins - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2003-02, Vol.13 (3), p.463-466</ispartof><rights>2002 Elsevier Science Ltd</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-f33e7d832726c4e7a9367c6157d7545328f286e0c9e07e9b0920bd9a2fcec6373</citedby><cites>FETCH-LOGICAL-c391t-f33e7d832726c4e7a9367c6157d7545328f286e0c9e07e9b0920bd9a2fcec6373</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X02009484$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14500127$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12565951$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kang, Yong Koo</creatorcontrib><creatorcontrib>Lee, Kyung Seok</creatorcontrib><creatorcontrib>Yoo, Kyung Ho</creatorcontrib><creatorcontrib>Shin, Kye Jung</creatorcontrib><creatorcontrib>Kim, Dong Chan</creatorcontrib><creatorcontrib>Lee, Chang-Seok</creatorcontrib><creatorcontrib>Kong, Jae Yang</creatorcontrib><creatorcontrib>Kim, Dong Jin</creatorcontrib><title>Synthesis and biological evaluation of novel 1β-methylcarbapenems with isothiazoloethenyl side chains</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The synthesis of novel 1β-methylcarbapenems
1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem.
The synthesis of novel 1β-methylcarbapenems
1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem.</description><subject>Animals</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacokinetics</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Bacteria - drug effects</subject><subject>Biological and medical sciences</subject><subject>Carbapenems - chemical synthesis</subject><subject>Carbapenems - pharmacokinetics</subject><subject>Carbapenems - pharmacology</subject><subject>Half-Life</subject><subject>Indicators and Reagents</subject><subject>Medical sciences</subject><subject>Meropenem</subject><subject>Mice</subject><subject>Microbial Sensitivity Tests</subject><subject>Oxidation-Reduction</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><subject>Thienamycins - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9u1DAQhy0EotvCI4B8AcEhMP4fnxCqKCBV6qEgcbMcZ0KMEnuJs4uWx-JB-kzNdlf02NNcvt_MT98Q8oLBOwZMv78Gq6GqrfzxBvhbACvrSj4iKya1rIQE9Zis_iMn5LSUXwBMgpRPyQnjSiur2Ip017s091hioT61tIl5yD9j8APFrR82fo450dzRlLc4UHbzrxpx7ndD8FPj15hwLPRPnHsaS5776P8u-QXAtBtoiS3S0PuYyjPypPNDwefHeUa-X3z6dv6lurz6_PX842UVhGVz1QmBpq0FN1wHicZboU3QTJnWKKkErztea4RgEQzaBiyHprWedwGDFkackdeHvesp_95gmd0YS8Bh8AnzpjgjAIDDHlQHMEy5lAk7t57i6KedY-D2gt2dYLe354C7O8FOLrmXxwObZsT2PnU0ugCvjoAvi8Zu8inEcs9JtbyB7wt8OHC46NhGnFwJEVPANk4YZtfm-ECVW08pmkg</recordid><startdate>20030210</startdate><enddate>20030210</enddate><creator>Kang, Yong Koo</creator><creator>Lee, Kyung Seok</creator><creator>Yoo, Kyung Ho</creator><creator>Shin, Kye Jung</creator><creator>Kim, Dong Chan</creator><creator>Lee, Chang-Seok</creator><creator>Kong, Jae Yang</creator><creator>Kim, Dong Jin</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>20030210</creationdate><title>Synthesis and biological evaluation of novel 1β-methylcarbapenems with isothiazoloethenyl side chains</title><author>Kang, Yong Koo ; Lee, Kyung Seok ; Yoo, Kyung Ho ; Shin, Kye Jung ; Kim, Dong Chan ; Lee, Chang-Seok ; Kong, Jae Yang ; Kim, Dong Jin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-f33e7d832726c4e7a9367c6157d7545328f286e0c9e07e9b0920bd9a2fcec6373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - pharmacokinetics</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Bacteria - drug effects</topic><topic>Biological and medical sciences</topic><topic>Carbapenems - chemical synthesis</topic><topic>Carbapenems - pharmacokinetics</topic><topic>Carbapenems - pharmacology</topic><topic>Half-Life</topic><topic>Indicators and Reagents</topic><topic>Medical sciences</topic><topic>Meropenem</topic><topic>Mice</topic><topic>Microbial Sensitivity Tests</topic><topic>Oxidation-Reduction</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><topic>Thienamycins - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kang, Yong Koo</creatorcontrib><creatorcontrib>Lee, Kyung Seok</creatorcontrib><creatorcontrib>Yoo, Kyung Ho</creatorcontrib><creatorcontrib>Shin, Kye Jung</creatorcontrib><creatorcontrib>Kim, Dong Chan</creatorcontrib><creatorcontrib>Lee, Chang-Seok</creatorcontrib><creatorcontrib>Kong, Jae Yang</creatorcontrib><creatorcontrib>Kim, Dong Jin</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>Kang, Yong Koo</au><au>Lee, Kyung Seok</au><au>Yoo, Kyung Ho</au><au>Shin, Kye Jung</au><au>Kim, Dong Chan</au><au>Lee, Chang-Seok</au><au>Kong, Jae Yang</au><au>Kim, Dong Jin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of novel 1β-methylcarbapenems with isothiazoloethenyl side chains</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2003-02-10</date><risdate>2003</risdate><volume>13</volume><issue>3</issue><spage>463</spage><epage>466</epage><pages>463-466</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The synthesis of novel 1β-methylcarbapenems
1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem.
The synthesis of novel 1β-methylcarbapenems
1a,
b bearing isothiazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. Especially, 5-isothiazole derivative
1a exhibited excellent DHP-I stability and advanced pharmacokinetics profiles, compared to 5-isoxazole derivative
2, imipenem, and meropenem.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>12565951</pmid><doi>10.1016/S0960-894X(02)00948-4</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2003-02, Vol.13 (3), p.463-466 |
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| subjects | Animals Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacokinetics Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Bacteria - drug effects Biological and medical sciences Carbapenems - chemical synthesis Carbapenems - pharmacokinetics Carbapenems - pharmacology Half-Life Indicators and Reagents Medical sciences Meropenem Mice Microbial Sensitivity Tests Oxidation-Reduction Pharmacology. Drug treatments Rats Structure-Activity Relationship Thienamycins - pharmacology |
| title | Synthesis and biological evaluation of novel 1β-methylcarbapenems with isothiazoloethenyl side chains |
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