A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities
4‘-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from d-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabin...
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| Veröffentlicht in: | Journal of medicinal chemistry 1997-07, Vol.40 (14), p.2177-2183 |
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| container_issue | 14 |
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| container_title | Journal of medicinal chemistry |
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| creator | Yoshimura, Yuichi Watanabe, Mikari Satoh, Hiroshi Ashida, Noriyuki Ijichi, Katsushi Sakata, Shinji Machida, Haruhiko Matsuda, Akira |
| description | 4‘-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from d-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (11), which was condensed with nucleobases to give 4‘-thioarabinonucleosides. The 5-substituted-4‘-thioaraU (6a−e) derivatives showed anti-HSV-1 activity (ED50 = 0.43−3.50 μg/mL). 4‘-ThioaraG (6h) and 2,6-diaminopurine 4‘-thioarabinonucleoside (4‘-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 μg/mL, respectively). |
| doi_str_mv | 10.1021/jm9701536 |
| format | Article |
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The 5-substituted-4‘-thioaraU (6a−e) derivatives showed anti-HSV-1 activity (ED50 = 0.43−3.50 μg/mL). 4‘-ThioaraG (6h) and 2,6-diaminopurine 4‘-thioarabinonucleoside (4‘-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 μg/mL, respectively).</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm9701536</identifier><identifier>PMID: 9216836</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Arabinonucleosides - chemical synthesis ; Arabinonucleosides - chemistry ; Arabinonucleosides - pharmacology ; Biological and medical sciences ; Cell Division - drug effects ; Cell Line ; Cytarabine - pharmacology ; Cytomegalovirus - drug effects ; Herpesviridae - drug effects ; Humans ; Indicators and Reagents ; Leukemia-Lymphoma, Adult T-Cell ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Structure ; Pharmacology. Drug treatments ; Structure-Activity Relationship ; Thionucleosides - chemical synthesis ; Thionucleosides - chemistry ; Thionucleosides - pharmacology ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 1997-07, Vol.40 (14), p.2177-2183</ispartof><rights>Copyright © 1997 American Chemical Society</rights><rights>1997 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a408t-896c4fda17c5fe286bddaf8fddaa0f374cda248feac4ed27e22bb80b6517693a3</citedby><cites>FETCH-LOGICAL-a408t-896c4fda17c5fe286bddaf8fddaa0f374cda248feac4ed27e22bb80b6517693a3</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/jm9701536$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm9701536$$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=2742686$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9216836$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yoshimura, Yuichi</creatorcontrib><creatorcontrib>Watanabe, Mikari</creatorcontrib><creatorcontrib>Satoh, Hiroshi</creatorcontrib><creatorcontrib>Ashida, Noriyuki</creatorcontrib><creatorcontrib>Ijichi, Katsushi</creatorcontrib><creatorcontrib>Sakata, Shinji</creatorcontrib><creatorcontrib>Machida, Haruhiko</creatorcontrib><creatorcontrib>Matsuda, Akira</creatorcontrib><title>A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>4‘-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from d-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (11), which was condensed with nucleobases to give 4‘-thioarabinonucleosides. The 5-substituted-4‘-thioaraU (6a−e) derivatives showed anti-HSV-1 activity (ED50 = 0.43−3.50 μg/mL). 4‘-ThioaraG (6h) and 2,6-diaminopurine 4‘-thioarabinonucleoside (4‘-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 μg/mL, respectively).</description><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Arabinonucleosides - chemical synthesis</subject><subject>Arabinonucleosides - chemistry</subject><subject>Arabinonucleosides - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Division - drug effects</subject><subject>Cell Line</subject><subject>Cytarabine - pharmacology</subject><subject>Cytomegalovirus - drug effects</subject><subject>Herpesviridae - drug effects</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>Leukemia-Lymphoma, Adult T-Cell</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><subject>Thionucleosides - chemical synthesis</subject><subject>Thionucleosides - chemistry</subject><subject>Thionucleosides - pharmacology</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0cGKFDEQBuAgyjquHnwAIQcVBFuTdDpJH8fFdYURlR0vHgzV6YqTMdNZk25xbz6Gz-eT2MsMcxK8JIf6-En-IuQhZy84E_zldtdqxpta3SIL3ghWScPkbbJgTIhKKFHfJfdK2TLGai7qE3LSCq5MrRbky5KegwsRn9NlHDEPMIYfSC-vh3GDJRSaPJV_fv2u1puQIEMXhjRMLmIqocdCYejpeoMh01chxfQ1OIh06eaQMAYs98kdD7Hgg8N9Sj6dv16fXVSr92_eni1XFUhmxsq0yknfA9eu8SiM6voevPHzCczXWroehDQewUnshUYhus6wTjVcq7aG-pQ83ede5fR9wjLaXSgOY4QB01Ssbvn8YcP-C7kSUgjezvDZHrqcSsno7VUOO8jXljN7U7o9lj7bR4fQqdthf5SHluf548McytyPzzC4UI5MaCmUuWHVnoUy4s_jGPI3q3StG7v-cGnlx0Z9Xr27sGb2T_YeXLHbNM3Li-Ufz_sLrUylkQ</recordid><startdate>19970704</startdate><enddate>19970704</enddate><creator>Yoshimura, Yuichi</creator><creator>Watanabe, Mikari</creator><creator>Satoh, Hiroshi</creator><creator>Ashida, Noriyuki</creator><creator>Ijichi, Katsushi</creator><creator>Sakata, Shinji</creator><creator>Machida, Haruhiko</creator><creator>Matsuda, Akira</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>7TM</scope><scope>7X8</scope></search><sort><creationdate>19970704</creationdate><title>A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities</title><author>Yoshimura, Yuichi ; Watanabe, Mikari ; Satoh, Hiroshi ; Ashida, Noriyuki ; Ijichi, Katsushi ; Sakata, Shinji ; Machida, Haruhiko ; Matsuda, Akira</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a408t-896c4fda17c5fe286bddaf8fddaa0f374cda248feac4ed27e22bb80b6517693a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Arabinonucleosides - chemical synthesis</topic><topic>Arabinonucleosides - chemistry</topic><topic>Arabinonucleosides - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Division - drug effects</topic><topic>Cell Line</topic><topic>Cytarabine - pharmacology</topic><topic>Cytomegalovirus - drug effects</topic><topic>Herpesviridae - drug effects</topic><topic>Humans</topic><topic>Indicators and Reagents</topic><topic>Leukemia-Lymphoma, Adult T-Cell</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><topic>Thionucleosides - chemical synthesis</topic><topic>Thionucleosides - chemistry</topic><topic>Thionucleosides - pharmacology</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yoshimura, Yuichi</creatorcontrib><creatorcontrib>Watanabe, Mikari</creatorcontrib><creatorcontrib>Satoh, Hiroshi</creatorcontrib><creatorcontrib>Ashida, Noriyuki</creatorcontrib><creatorcontrib>Ijichi, Katsushi</creatorcontrib><creatorcontrib>Sakata, Shinji</creatorcontrib><creatorcontrib>Machida, Haruhiko</creatorcontrib><creatorcontrib>Matsuda, Akira</creatorcontrib><collection>Istex</collection><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>Nucleic Acids Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yoshimura, Yuichi</au><au>Watanabe, Mikari</au><au>Satoh, Hiroshi</au><au>Ashida, Noriyuki</au><au>Ijichi, Katsushi</au><au>Sakata, Shinji</au><au>Machida, Haruhiko</au><au>Matsuda, Akira</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1997-07-04</date><risdate>1997</risdate><volume>40</volume><issue>14</issue><spage>2177</spage><epage>2183</epage><pages>2177-2183</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>4‘-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from d-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hydroxyl groups to give 1-O-acetyl-4-thioarabinose (11), which was condensed with nucleobases to give 4‘-thioarabinonucleosides. The 5-substituted-4‘-thioaraU (6a−e) derivatives showed anti-HSV-1 activity (ED50 = 0.43−3.50 μg/mL). 4‘-ThioaraG (6h) and 2,6-diaminopurine 4‘-thioarabinonucleoside (4‘-thioaraDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.022 μg/mL, respectively).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>9216836</pmid><doi>10.1021/jm9701536</doi><tpages>7</tpages></addata></record> |
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| subjects | Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Arabinonucleosides - chemical synthesis Arabinonucleosides - chemistry Arabinonucleosides - pharmacology Biological and medical sciences Cell Division - drug effects Cell Line Cytarabine - pharmacology Cytomegalovirus - drug effects Herpesviridae - drug effects Humans Indicators and Reagents Leukemia-Lymphoma, Adult T-Cell Medical sciences Microbial Sensitivity Tests Molecular Structure Pharmacology. Drug treatments Structure-Activity Relationship Thionucleosides - chemical synthesis Thionucleosides - chemistry Thionucleosides - pharmacology Tumor Cells, Cultured |
| title | A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities |
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