A Facile Method for Synthesis of N-Acyloxymethyl-5-fluorouracils, as a Class of Antitumor Agents
Antitumor-active derivatives of 5-fluorouracil were prepared via a new method by introducing an acyloxymethyl group at the 1-, 3-, or 1, 3-position (s). These derivatives were obtained by condensing 1, 3-bis (hydroxymethyl) -5-fluorouracil with various short-/long-chain carboxylic acids or their der...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1987/10/25, Vol.35(10), pp.4137-4143 |
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| container_end_page | 4143 |
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| container_issue | 10 |
| container_start_page | 4137 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 35 |
| creator | AHMAD, SUHAIL OZAKI, SHOICHIRO NAGASE, TOSHIO IIGO, MASAAKI TOKUZEN, REIKO HOSHI, AKIO |
| description | Antitumor-active derivatives of 5-fluorouracil were prepared via a new method by introducing an acyloxymethyl group at the 1-, 3-, or 1, 3-position (s). These derivatives were obtained by condensing 1, 3-bis (hydroxymethyl) -5-fluorouracil with various short-/long-chain carboxylic acids or their derivatives, in the presence of dicyclohexylcarbodiimide and a catalytic amount of N, N-dimethylaminopyridine. Some of the derivatives showed strong antitumor activity against the leukemia L1210 system when administered orally. |
| doi_str_mv | 10.1248/cpb.35.4137 |
| format | Article |
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These derivatives were obtained by condensing 1, 3-bis (hydroxymethyl) -5-fluorouracil with various short-/long-chain carboxylic acids or their derivatives, in the presence of dicyclohexylcarbodiimide and a catalytic amount of N, N-dimethylaminopyridine. Some of the derivatives showed strong antitumor activity against the leukemia L1210 system when administered orally.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.35.4137</identifier><identifier>PMID: 3435940</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>1, 3-bis (hydroxymethyl) -5-fluorouracil ; 1-undecenoyloxymethyl-5-fluorouracil ; 5-fluorouracil ; acyloxymethyl-5-fluorouracil ; Animals ; Antineoplastic Agents - chemical synthesis ; antitumor agent ; Chemical Phenomena ; Chemistry ; dicyclohexylcarbodiimide ; Exact sciences and technology ; Fluorouracil - analogs & derivatives ; Fluorouracil - chemical synthesis ; Fluorouracil - pharmacology ; 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 ; Preparations and properties</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1987/10/25, Vol.35(10), pp.4137-4143</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1988 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1987</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5527-3dc881ed94051721fad990d49d5c858ee7f93a2bad085f7f3c80705b73ae782a3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7818736$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3435940$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>AHMAD, SUHAIL</creatorcontrib><creatorcontrib>OZAKI, SHOICHIRO</creatorcontrib><creatorcontrib>NAGASE, TOSHIO</creatorcontrib><creatorcontrib>IIGO, MASAAKI</creatorcontrib><creatorcontrib>TOKUZEN, REIKO</creatorcontrib><creatorcontrib>HOSHI, AKIO</creatorcontrib><title>A Facile Method for Synthesis of N-Acyloxymethyl-5-fluorouracils, as a Class of Antitumor Agents</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Antitumor-active derivatives of 5-fluorouracil were prepared via a new method by introducing an acyloxymethyl group at the 1-, 3-, or 1, 3-position (s). These derivatives were obtained by condensing 1, 3-bis (hydroxymethyl) -5-fluorouracil with various short-/long-chain carboxylic acids or their derivatives, in the presence of dicyclohexylcarbodiimide and a catalytic amount of N, N-dimethylaminopyridine. Some of the derivatives showed strong antitumor activity against the leukemia L1210 system when administered orally.</description><subject>1, 3-bis (hydroxymethyl) -5-fluorouracil</subject><subject>1-undecenoyloxymethyl-5-fluorouracil</subject><subject>5-fluorouracil</subject><subject>acyloxymethyl-5-fluorouracil</subject><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>antitumor agent</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>dicyclohexylcarbodiimide</subject><subject>Exact sciences and technology</subject><subject>Fluorouracil - analogs & derivatives</subject><subject>Fluorouracil - chemical synthesis</subject><subject>Fluorouracil - pharmacology</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>Preparations and properties</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkUGP0zAQhS0EWkrhxBnJEogLpNieeO0co4oC0gIH4Gymjr1N5STFTiTy73FoVSQu9mE-v_fmmZDnnG24KPU7e9pvQG5KDuoBWXEoVSGFgIdkxRirCgG38Jg8SenImJBMwQ25gRJkVbIV-VnTHdo2OPrZjYehoX6I9NvcjweX2kQHT78UtZ3D8HvuMjCHQhY-TEMcpri8S28pJop0GzD9xet-bMepyyr1vevH9JQ88hiSe3a51-TH7v337cfi7uuHT9v6rrBSClVAY7XmrsmhJFeCe2yqijVl1UirpXZO-QpQ7LFhWnrlwWqmmNwrQKe0QFiT12fdUxx-TS6NpmuTdSFg74YpGaUqAKlUBl_-Bx7zLn3OZnh5y3jJJReZenOmbBxSis6bU2w7jLPhzCytm9y6AWmW1jP94qI57TvXXNlLzXn-6jLHZDH4iL1t0xVTmmuVf2lNdmfsmEa8d9c5xrG1wS2WvJJ6sc0pzufi_w84YDSuhz9BgaCs</recordid><startdate>1987</startdate><enddate>1987</enddate><creator>AHMAD, SUHAIL</creator><creator>OZAKI, SHOICHIRO</creator><creator>NAGASE, TOSHIO</creator><creator>IIGO, MASAAKI</creator><creator>TOKUZEN, REIKO</creator><creator>HOSHI, AKIO</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>1987</creationdate><title>A Facile Method for Synthesis of N-Acyloxymethyl-5-fluorouracils, as a Class of Antitumor Agents</title><author>AHMAD, SUHAIL ; OZAKI, SHOICHIRO ; NAGASE, TOSHIO ; IIGO, MASAAKI ; TOKUZEN, REIKO ; HOSHI, AKIO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5527-3dc881ed94051721fad990d49d5c858ee7f93a2bad085f7f3c80705b73ae782a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>1, 3-bis (hydroxymethyl) -5-fluorouracil</topic><topic>1-undecenoyloxymethyl-5-fluorouracil</topic><topic>5-fluorouracil</topic><topic>acyloxymethyl-5-fluorouracil</topic><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>antitumor agent</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>dicyclohexylcarbodiimide</topic><topic>Exact sciences and technology</topic><topic>Fluorouracil - analogs & derivatives</topic><topic>Fluorouracil - chemical synthesis</topic><topic>Fluorouracil - pharmacology</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>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>AHMAD, SUHAIL</creatorcontrib><creatorcontrib>OZAKI, SHOICHIRO</creatorcontrib><creatorcontrib>NAGASE, TOSHIO</creatorcontrib><creatorcontrib>IIGO, MASAAKI</creatorcontrib><creatorcontrib>TOKUZEN, REIKO</creatorcontrib><creatorcontrib>HOSHI, AKIO</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>AHMAD, SUHAIL</au><au>OZAKI, SHOICHIRO</au><au>NAGASE, TOSHIO</au><au>IIGO, MASAAKI</au><au>TOKUZEN, REIKO</au><au>HOSHI, AKIO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Facile Method for Synthesis of N-Acyloxymethyl-5-fluorouracils, as a Class of Antitumor Agents</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1987</date><risdate>1987</risdate><volume>35</volume><issue>10</issue><spage>4137</spage><epage>4143</epage><pages>4137-4143</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Antitumor-active derivatives of 5-fluorouracil were prepared via a new method by introducing an acyloxymethyl group at the 1-, 3-, or 1, 3-position (s). These derivatives were obtained by condensing 1, 3-bis (hydroxymethyl) -5-fluorouracil with various short-/long-chain carboxylic acids or their derivatives, in the presence of dicyclohexylcarbodiimide and a catalytic amount of N, N-dimethylaminopyridine. Some of the derivatives showed strong antitumor activity against the leukemia L1210 system when administered orally.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>3435940</pmid><doi>10.1248/cpb.35.4137</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1987/10/25, Vol.35(10), pp.4137-4143 |
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| language | eng |
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| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 1, 3-bis (hydroxymethyl) -5-fluorouracil 1-undecenoyloxymethyl-5-fluorouracil 5-fluorouracil acyloxymethyl-5-fluorouracil Animals Antineoplastic Agents - chemical synthesis antitumor agent Chemical Phenomena Chemistry dicyclohexylcarbodiimide Exact sciences and technology Fluorouracil - analogs & derivatives Fluorouracil - chemical synthesis Fluorouracil - pharmacology 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 Preparations and properties |
| title | A Facile Method for Synthesis of N-Acyloxymethyl-5-fluorouracils, as a Class of Antitumor Agents |
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