Uracil Derivatives. IV. Growth-Inhibitory Activity against L-1210 Cells of Orotic Acid Derivatives and Synthesis of 1-(β-D-Ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione
5-(Substituted thiomethyl)-6-carbamoyluracils (IIIb-h) and 5-(substituted thiomethyl)-uracils (Va-h) were prepared and their ability to inhibit the growth of L-1210 cells in vitro was examined. The reaction of silylated furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VI) with 1-O-acetyl-2, 3,...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1983/09/25, Vol.31(9), pp.3074-3083 |
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| creator | OKADA, JUTARO NAKANO, KOICHI MIYAKE, HIROSHI |
| description | 5-(Substituted thiomethyl)-6-carbamoyluracils (IIIb-h) and 5-(substituted thiomethyl)-uracils (Va-h) were prepared and their ability to inhibit the growth of L-1210 cells in vitro was examined. The reaction of silylated furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VI) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VII) in acetonitrile in the presence of SnCl4 gave 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VIII) in 81.0% yield. The protected nucleoside (VIII) was hydrolyzed by sodium methoxide to give the N1-nucleoside (X). |
| doi_str_mv | 10.1248/cpb.31.3074 |
| format | Article |
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IV. Growth-Inhibitory Activity against L-1210 Cells of Orotic Acid Derivatives and Synthesis of 1-(β-D-Ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione</title><source>J-STAGE Free</source><source>MEDLINE</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>OKADA, JUTARO ; NAKANO, KOICHI ; MIYAKE, HIROSHI</creator><creatorcontrib>OKADA, JUTARO ; NAKANO, KOICHI ; MIYAKE, HIROSHI</creatorcontrib><description>5-(Substituted thiomethyl)-6-carbamoyluracils (IIIb-h) and 5-(substituted thiomethyl)-uracils (Va-h) were prepared and their ability to inhibit the growth of L-1210 cells in vitro was examined. The reaction of silylated furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VI) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VII) in acetonitrile in the presence of SnCl4 gave 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VIII) in 81.0% yield. The protected nucleoside (VIII) was hydrolyzed by sodium methoxide to give the N1-nucleoside (X).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.31.3074</identifier><identifier>PMID: 6667528</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>1H-NMR ; Animals ; Antineoplastic Agents - chemical synthesis ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Leukemia L1210 - drug therapy ; Mice ; Organic chemistry ; Orotic Acid - analogs & derivatives ; Orotic Acid - chemical synthesis ; Orotic Acid - pharmacology ; Preparations and properties ; Pyrimidine Nucleosides - chemical synthesis ; Pyrimidine Nucleosides - pharmacology</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1983/09/25, Vol.31(9), pp.3074-3083</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1984 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1983</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4824-b76d3dd6ff76b388e6da6cd92c2b0fa0c17012ff299b283318d400060b2b83cf3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,4014,27914,27915,27916</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9378676$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6667528$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>OKADA, JUTARO</creatorcontrib><creatorcontrib>NAKANO, KOICHI</creatorcontrib><creatorcontrib>MIYAKE, HIROSHI</creatorcontrib><title>Uracil Derivatives. IV. Growth-Inhibitory Activity against L-1210 Cells of Orotic Acid Derivatives and Synthesis of 1-(β-D-Ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>5-(Substituted thiomethyl)-6-carbamoyluracils (IIIb-h) and 5-(substituted thiomethyl)-uracils (Va-h) were prepared and their ability to inhibit the growth of L-1210 cells in vitro was examined. The reaction of silylated furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VI) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VII) in acetonitrile in the presence of SnCl4 gave 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VIII) in 81.0% yield. The protected nucleoside (VIII) was hydrolyzed by sodium methoxide to give the N1-nucleoside (X).</description><subject>1H-NMR</subject><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Leukemia L1210 - drug therapy</subject><subject>Mice</subject><subject>Organic chemistry</subject><subject>Orotic Acid - analogs & derivatives</subject><subject>Orotic Acid - chemical synthesis</subject><subject>Orotic Acid - pharmacology</subject><subject>Preparations and properties</subject><subject>Pyrimidine Nucleosides - chemical synthesis</subject><subject>Pyrimidine Nucleosides - pharmacology</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkd2KEzEYhgdR1rp65LEQUGQXm5qfmSRzuLS6LRQW1PVEZMjkZ5syndRkujK35Q14B16TGTtU8SA_5H14v3zfm2XPMZphkou3al_PKJ5RxPMH2QTTnMOCEPowmyCESkgoo4-zJzFuESIF4vQsO2OM8YKISfbzNkjlGrAwwd3Lzt2bOAOrzzNwHfz3bgNX7cbVrvOhB1cqya7rgbyTro0dWENMMAJz0zQReAtugu-cSpzT__oB2WrwsW-7jYnuD4jhxa8fcAE_uNrbQ5Ctj31zCdLVgy90CnKov4J9H9zOadcaSNLTFHBwgZdTQNMqlpewC8635mn2yMommmfjeZ7dvn_3ab6E65vr1fxqDVUuSA5rzjTVmlnLWU2FMExLpnRJFKmRlUhhjjCxlpRlTQSlWOg8DY-hmtSCKkvPs9dH333w3w4mdtXORZU6l63xh1gJJPgw7QS-_A_c-kNo098qnBdlmacEBurNkVLBxxiMrfapWxn6CqNqCLVKoVYUV0OoiX4xeh7qndEndkwx6a9GXUYlG5smqlw8YSXlgnGWsMUR28ZO3pmTLkOKrTFDSVwWYihbjluq_lfeyFCZlv4GGvC-VA</recordid><startdate>1983</startdate><enddate>1983</enddate><creator>OKADA, JUTARO</creator><creator>NAKANO, KOICHI</creator><creator>MIYAKE, HIROSHI</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>1983</creationdate><title>Uracil Derivatives. IV. Growth-Inhibitory Activity against L-1210 Cells of Orotic Acid Derivatives and Synthesis of 1-(β-D-Ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione</title><author>OKADA, JUTARO ; NAKANO, KOICHI ; MIYAKE, HIROSHI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4824-b76d3dd6ff76b388e6da6cd92c2b0fa0c17012ff299b283318d400060b2b83cf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>1H-NMR</topic><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Leukemia L1210 - drug therapy</topic><topic>Mice</topic><topic>Organic chemistry</topic><topic>Orotic Acid - analogs & derivatives</topic><topic>Orotic Acid - chemical synthesis</topic><topic>Orotic Acid - pharmacology</topic><topic>Preparations and properties</topic><topic>Pyrimidine Nucleosides - chemical synthesis</topic><topic>Pyrimidine Nucleosides - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>OKADA, JUTARO</creatorcontrib><creatorcontrib>NAKANO, KOICHI</creatorcontrib><creatorcontrib>MIYAKE, HIROSHI</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>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>OKADA, JUTARO</au><au>NAKANO, KOICHI</au><au>MIYAKE, HIROSHI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Uracil Derivatives. IV. Growth-Inhibitory Activity against L-1210 Cells of Orotic Acid Derivatives and Synthesis of 1-(β-D-Ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1983</date><risdate>1983</risdate><volume>31</volume><issue>9</issue><spage>3074</spage><epage>3083</epage><pages>3074-3083</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>5-(Substituted thiomethyl)-6-carbamoyluracils (IIIb-h) and 5-(substituted thiomethyl)-uracils (Va-h) were prepared and their ability to inhibit the growth of L-1210 cells in vitro was examined. The reaction of silylated furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VI) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VII) in acetonitrile in the presence of SnCl4 gave 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VIII) in 81.0% yield. The protected nucleoside (VIII) was hydrolyzed by sodium methoxide to give the N1-nucleoside (X).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>6667528</pmid><doi>10.1248/cpb.31.3074</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| recordid | cdi_proquest_miscellaneous_80870009 |
| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 1H-NMR Animals Antineoplastic Agents - chemical synthesis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Leukemia L1210 - drug therapy Mice Organic chemistry Orotic Acid - analogs & derivatives Orotic Acid - chemical synthesis Orotic Acid - pharmacology Preparations and properties Pyrimidine Nucleosides - chemical synthesis Pyrimidine Nucleosides - pharmacology |
| title | Uracil Derivatives. IV. Growth-Inhibitory Activity against L-1210 Cells of Orotic Acid Derivatives and Synthesis of 1-(β-D-Ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione |
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