Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties
The synthesis and antifungal activity of 5′- and 5′-6′-substituted azasordarin derivatives are described. Modification of the 5′-position led to the discovery of the spirocyclopentyl analogue 7g, which is the first azasordarin to register single-digit MIC values versus Aspergillus spp. Further inves...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2003-04, Vol.13 (8), p.1419-1423 |
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| creator | Serrano-Wu, Michael H. Laurent, Denis R.St Carroll, Tina M. Dodier, Marco Gao, Qi Gill, Patrice Quesnelle, Claude Marinier, Anne Mazzucco, Charles E. Regueiro-Ren, Alicia Stickle, Terry M. Wu, Dedong Yang, Hyekyung Yang, Zheng Zheng, Ming Zoeckler, Mary E. Vyas, Dolatrai M. Balasubramanian, Balu N. |
| description | The synthesis and antifungal activity of 5′- and 5′-6′-substituted azasordarin derivatives are described. Modification of the 5′-position led to the discovery of the spirocyclopentyl analogue
7g, which is the first azasordarin to register single-digit MIC values versus
Aspergillus spp. Further investigation identified the 5′-
i-Pr derivative
7b, which displays superior pharmacokinetic properties compared to other azasordarins.
The synthesis and antifungal activity of novel azasordarin derivatives are described. |
| doi_str_mv | 10.1016/S0960-894X(03)00161-6 |
| format | Article |
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7g, which is the first azasordarin to register single-digit MIC values versus
Aspergillus spp. Further investigation identified the 5′-
i-Pr derivative
7b, which displays superior pharmacokinetic properties compared to other azasordarins.
The synthesis and antifungal activity of novel azasordarin derivatives are described.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(03)00161-6</identifier><identifier>PMID: 12668003</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Administration, Oral ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal agents ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacokinetics ; Antifungal Agents - pharmacology ; Aspergillus - drug effects ; Aza Compounds - chemical synthesis ; Aza Compounds - chemistry ; Aza Compounds - pharmacokinetics ; Aza Compounds - pharmacology ; Biological and medical sciences ; Glycosides - chemistry ; Indenes ; Injections, Intravenous ; Medical sciences ; Mice ; Microbial Sensitivity Tests ; Pharmacology. Drug treatments ; Spiro Compounds - chemistry ; Spiro Compounds - pharmacokinetics ; Spiro Compounds - pharmacology ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2003-04, Vol.13 (8), p.1419-1423</ispartof><rights>2003 Elsevier Science Ltd</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-262b80a581f5c3de328dc367967a2a589951148cb682ad509dd723deba7889103</citedby><cites>FETCH-LOGICAL-c391t-262b80a581f5c3de328dc367967a2a589951148cb682ad509dd723deba7889103</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X03001616$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14640602$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12668003$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Serrano-Wu, Michael H.</creatorcontrib><creatorcontrib>Laurent, Denis R.St</creatorcontrib><creatorcontrib>Carroll, Tina M.</creatorcontrib><creatorcontrib>Dodier, Marco</creatorcontrib><creatorcontrib>Gao, Qi</creatorcontrib><creatorcontrib>Gill, Patrice</creatorcontrib><creatorcontrib>Quesnelle, Claude</creatorcontrib><creatorcontrib>Marinier, Anne</creatorcontrib><creatorcontrib>Mazzucco, Charles E.</creatorcontrib><creatorcontrib>Regueiro-Ren, Alicia</creatorcontrib><creatorcontrib>Stickle, Terry M.</creatorcontrib><creatorcontrib>Wu, Dedong</creatorcontrib><creatorcontrib>Yang, Hyekyung</creatorcontrib><creatorcontrib>Yang, Zheng</creatorcontrib><creatorcontrib>Zheng, Ming</creatorcontrib><creatorcontrib>Zoeckler, Mary E.</creatorcontrib><creatorcontrib>Vyas, Dolatrai M.</creatorcontrib><creatorcontrib>Balasubramanian, Balu N.</creatorcontrib><title>Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The synthesis and antifungal activity of 5′- and 5′-6′-substituted azasordarin derivatives are described. Modification of the 5′-position led to the discovery of the spirocyclopentyl analogue
7g, which is the first azasordarin to register single-digit MIC values versus
Aspergillus spp. Further investigation identified the 5′-
i-Pr derivative
7b, which displays superior pharmacokinetic properties compared to other azasordarins.
The synthesis and antifungal activity of novel azasordarin derivatives are described.</description><subject>Administration, Oral</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacokinetics</subject><subject>Antifungal Agents - pharmacology</subject><subject>Aspergillus - drug effects</subject><subject>Aza Compounds - chemical synthesis</subject><subject>Aza Compounds - chemistry</subject><subject>Aza Compounds - pharmacokinetics</subject><subject>Aza Compounds - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Glycosides - chemistry</subject><subject>Indenes</subject><subject>Injections, Intravenous</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Microbial Sensitivity Tests</subject><subject>Pharmacology. Drug treatments</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - pharmacokinetics</subject><subject>Spiro Compounds - pharmacology</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</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>eNqFkUtv1TAQRi0Eam9LfwIoG1C7CIwfcZxVhSr6kCqxKAh21sSeqKY3cWrnFsGvx-29oktWI30689AZxt5w-MCB64830GmoTad-HIM8gRLxWr9gK660qqWC5iVb_UP22UHOPwukQKk9ts-F1gZArtj3K0_TEobgcAlxquJQYdWniL6-mcktaTNW-AdzTB5TmKpfYbmtwjin-EC-mm8xjejiXZhoCa4q8UxpCZRfs1cDrjMd7eoh-3b--evZZX395eLq7NN17WTHl1po0RvAxvChcdKTFMY7qdtOtyhK3HUN58q4XhuBvoHO-1YUrsfWmI6DPGTvt3PL6vsN5cWOITtar3GiuMm2lbxRQjQFbLagSzHnRIOdUxgx_bYc7KNR-2TUPuqyIO2TUatL39vdgk0_kn_u2ikswLsdgNnhekg4uZCfufIP0CAKd7rlqOh4CJRsdoEmRz6kItr6GP5zyl9JRJOJ</recordid><startdate>20030417</startdate><enddate>20030417</enddate><creator>Serrano-Wu, Michael H.</creator><creator>Laurent, Denis R.St</creator><creator>Carroll, Tina M.</creator><creator>Dodier, Marco</creator><creator>Gao, Qi</creator><creator>Gill, Patrice</creator><creator>Quesnelle, Claude</creator><creator>Marinier, Anne</creator><creator>Mazzucco, Charles E.</creator><creator>Regueiro-Ren, Alicia</creator><creator>Stickle, Terry M.</creator><creator>Wu, Dedong</creator><creator>Yang, Hyekyung</creator><creator>Yang, Zheng</creator><creator>Zheng, Ming</creator><creator>Zoeckler, Mary E.</creator><creator>Vyas, Dolatrai M.</creator><creator>Balasubramanian, Balu N.</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>20030417</creationdate><title>Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties</title><author>Serrano-Wu, Michael H. ; Laurent, Denis R.St ; Carroll, Tina M. ; Dodier, Marco ; Gao, Qi ; Gill, Patrice ; Quesnelle, Claude ; Marinier, Anne ; Mazzucco, Charles E. ; Regueiro-Ren, Alicia ; Stickle, Terry M. ; Wu, Dedong ; Yang, Hyekyung ; Yang, Zheng ; Zheng, Ming ; Zoeckler, Mary E. ; Vyas, Dolatrai M. ; Balasubramanian, Balu N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-262b80a581f5c3de328dc367967a2a589951148cb682ad509dd723deba7889103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Administration, Oral</topic><topic>Animals</topic><topic>Antibiotics. 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Modification of the 5′-position led to the discovery of the spirocyclopentyl analogue
7g, which is the first azasordarin to register single-digit MIC values versus
Aspergillus spp. Further investigation identified the 5′-
i-Pr derivative
7b, which displays superior pharmacokinetic properties compared to other azasordarins.
The synthesis and antifungal activity of novel azasordarin derivatives are described.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>12668003</pmid><doi>10.1016/S0960-894X(03)00161-6</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2003-04, Vol.13 (8), p.1419-1423 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Administration, Oral Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemistry Antifungal Agents - pharmacokinetics Antifungal Agents - pharmacology Aspergillus - drug effects Aza Compounds - chemical synthesis Aza Compounds - chemistry Aza Compounds - pharmacokinetics Aza Compounds - pharmacology Biological and medical sciences Glycosides - chemistry Indenes Injections, Intravenous Medical sciences Mice Microbial Sensitivity Tests Pharmacology. Drug treatments Spiro Compounds - chemistry Spiro Compounds - pharmacokinetics Spiro Compounds - pharmacology Stereoisomerism Structure-Activity Relationship |
| title | Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties |
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