Syntheses and Antitumor Activities of 5-(Substituted-methyl)-6-carbamoyluracils
5-Chloromethyl-6-ethoxycarbonyluracil (5) was prepared from furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (4). Reaction of 5 with some nucleophilic reagents such as secondary amines, alcohols and sodium thiolates afforded 5-(substituted-methyl)-6-ethoxy-carbonyluracils. By treatment of the co...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1981/03/25, Vol.29(3), pp.667-675 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | OKADA, JUTARO NAKANO, KOICHI MIYAKE, HIROSHI |
| description | 5-Chloromethyl-6-ethoxycarbonyluracil (5) was prepared from furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (4). Reaction of 5 with some nucleophilic reagents such as secondary amines, alcohols and sodium thiolates afforded 5-(substituted-methyl)-6-ethoxy-carbonyluracils. By treatment of the corresponding esters with methanolic ammonia or ammonia water, 5-(substituted-methyl)-6-carbamoyluracils were prepared. The antitumor activities of the newly synthesized compounds were examined against L-1210 cells in vitro. |
| doi_str_mv | 10.1248/cpb.29.667 |
| format | Article |
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Reaction of 5 with some nucleophilic reagents such as secondary amines, alcohols and sodium thiolates afforded 5-(substituted-methyl)-6-ethoxy-carbonyluracils. By treatment of the corresponding esters with methanolic ammonia or ammonia water, 5-(substituted-methyl)-6-carbamoyluracils were prepared. 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Pharm. Bull.</addtitle><description>5-Chloromethyl-6-ethoxycarbonyluracil (5) was prepared from furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (4). Reaction of 5 with some nucleophilic reagents such as secondary amines, alcohols and sodium thiolates afforded 5-(substituted-methyl)-6-ethoxy-carbonyluracils. By treatment of the corresponding esters with methanolic ammonia or ammonia water, 5-(substituted-methyl)-6-carbamoyluracils were prepared. The antitumor activities of the newly synthesized compounds were examined against L-1210 cells in vitro.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>growth inhibition of L-1210 cells</subject><subject>Mice</subject><subject>Thymine - analogs & derivatives</subject><subject>Thymine - chemical synthesis</subject><subject>Thymine - pharmacology</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1981</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtrGzEURkVpSVynm-wDhkBpC3L0HElLY9omEMgiyVpopDvxmHm4kibgf18ZmxSy6UZ3cQ4fV_dD6JKSJWVC3_hdvWRmWVXqA5pRLhSWjPGPaEYIMZjxip-jzyltCWGSKH6GzhQThkoxQw-P-yFvIEFauCEsVkNu89SPcbHyuX1tc1vA2Cwk_vY41ekAMwTcQ97su--4wt7F2vXjvpui822XLtCnxnUJvpzmHD3_-vm0vsX3D7_v1qt77CU1CmsNpPHCMR84pzqEKlQMgtbeKUEod6ahnDeuEbUHAK5cYI4yz4KgUNPA5-jrMXcXxz8TpGz7NnnoOjfAOCWruBSCqOq_IpWcKGNoEa_fidtxikP5hKVCGq0FKyvN0Y-j5eOYUoTG7mLbu7i3lNhDGbaUYZmxpYwiX50ip7qH8Kaerl_4-si3KbsXeOMu5tZ3cIiiRupDHD8-JfUf3bhoYeB_AVCGnKU</recordid><startdate>1981</startdate><enddate>1981</enddate><creator>OKADA, JUTARO</creator><creator>NAKANO, KOICHI</creator><creator>MIYAKE, HIROSHI</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>1981</creationdate><title>Syntheses and Antitumor Activities of 5-(Substituted-methyl)-6-carbamoyluracils</title><author>OKADA, JUTARO ; NAKANO, KOICHI ; MIYAKE, HIROSHI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5197-88e0fc4a2cd3318dd6d62ed88ca74013a9f133faf4bceee37ad2a12c2d41eb1d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1981</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>growth inhibition of L-1210 cells</topic><topic>Mice</topic><topic>Thymine - analogs & derivatives</topic><topic>Thymine - chemical synthesis</topic><topic>Thymine - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>OKADA, JUTARO</creatorcontrib><creatorcontrib>NAKANO, KOICHI</creatorcontrib><creatorcontrib>MIYAKE, HIROSHI</creatorcontrib><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>Syntheses and Antitumor Activities of 5-(Substituted-methyl)-6-carbamoyluracils</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1981</date><risdate>1981</risdate><volume>29</volume><issue>3</issue><spage>667</spage><epage>675</epage><pages>667-675</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>5-Chloromethyl-6-ethoxycarbonyluracil (5) was prepared from furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (4). Reaction of 5 with some nucleophilic reagents such as secondary amines, alcohols and sodium thiolates afforded 5-(substituted-methyl)-6-ethoxy-carbonyluracils. By treatment of the corresponding esters with methanolic ammonia or ammonia water, 5-(substituted-methyl)-6-carbamoyluracils were prepared. The antitumor activities of the newly synthesized compounds were examined against L-1210 cells in vitro.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>7249154</pmid><doi>10.1248/cpb.29.667</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1981/03/25, Vol.29(3), pp.667-675 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | MEDLINE; Free Full-Text Journals in Chemistry; EZB Electronic Journals Library; J-STAGE |
| subjects | Animals Antineoplastic Agents - chemical synthesis growth inhibition of L-1210 cells Mice Thymine - analogs & derivatives Thymine - chemical synthesis Thymine - pharmacology |
| title | Syntheses and Antitumor Activities of 5-(Substituted-methyl)-6-carbamoyluracils |
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