Studies on Hepatic Agents. I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles
For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoaceton...
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Veröffentlicht in: | Chemical & pharmaceutical bulletin 1968/08/25, Vol.16(8), pp.1417-1432 |
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creator | SUZUE, SEIGO IRIKURA, TUTOMU |
description | For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoacetonitriles. VIII were converted to 2-hydroxyimino-5-oxopiperazine derivatives (XV) and 5-oxo-2-thio-piperazines (XX). Preparations of N-(N-acylaminoacyl) aminoacetonitriles were also described. Further, N-α-hydroxyacylaminoacetonitriles were prepared from chloralides of α-hydroxyacids with aminoacetonitrile. In addition, XV (R=H) was converted to 2-acetamino-5-acetoxypyrazine by treatment with acetic anhydride. |
doi_str_mv | 10.1248/cpb.16.1417 |
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I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles</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>SUZUE, SEIGO ; IRIKURA, TUTOMU</creator><creatorcontrib>SUZUE, SEIGO ; IRIKURA, TUTOMU</creatorcontrib><description>For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoacetonitriles. VIII were converted to 2-hydroxyimino-5-oxopiperazine derivatives (XV) and 5-oxo-2-thio-piperazines (XX). Preparations of N-(N-acylaminoacyl) aminoacetonitriles were also described. Further, N-α-hydroxyacylaminoacetonitriles were prepared from chloralides of α-hydroxyacids with aminoacetonitrile. In addition, XV (R=H) was converted to 2-acetamino-5-acetoxypyrazine by treatment with acetic anhydride.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.16.1417</identifier><identifier>PMID: 5708244</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Chemical and Drug Induced Liver Injury ; Lathyrism ; Nitriles - chemical synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1968/08/25, Vol.16(8), pp.1417-1432</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 1968</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c509t-afc05e9eaee3b42f30c654b6e0bdb1dfd531342fb4ee324738ffb2c0d4d112d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1882,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/5708244$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SUZUE, SEIGO</creatorcontrib><creatorcontrib>IRIKURA, TUTOMU</creatorcontrib><title>Studies on Hepatic Agents. 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In addition, XV (R=H) was converted to 2-acetamino-5-acetoxypyrazine by treatment with acetic anhydride.</description><subject>Chemical and Drug Induced Liver Injury</subject><subject>Lathyrism</subject><subject>Nitriles - chemical synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1968</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkEtLw0AURgdRan2sXAsBN4okzjOPZamPCoKLduNqmGTuaEqaxJkpmH_vhNa6mQtzPs7lfghdEZwQyvOHqi8TkiaEk-wITQnjWSwoZcdoijEuYspSdorOnFtjTAXO2ARNRIZzyvkUfSz9Vtfgoq6NFtArX1fR7BNa75LoNYmWQ-u_wNWBm2i2qdtOVUMT3apWR4tB2-5nGD_u_hj4rq29rRtwF-jEqMbB5X6eo9Xz02q-iN_eX17ns7e4ErjwsTIVFlCAAmAlp4bhKhW8TAGXuiTaaMHCRdSUPAQoz1huTEkrrLkmhGp2jm522t5231twXq67rW3DRkm4KDIiaI5D6n6XqmznnAUje1tvlB0kwXIsUYYSJUnlWGJIX--d23ID-pDdtxb4446vnVefcODKhvoaGF2kEPno-3uC9h9_KSuhZb_asoVD</recordid><startdate>19680101</startdate><enddate>19680101</enddate><creator>SUZUE, SEIGO</creator><creator>IRIKURA, TUTOMU</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></search><sort><creationdate>19680101</creationdate><title>Studies on Hepatic Agents. 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I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1968-01-01</date><risdate>1968</risdate><volume>16</volume><issue>8</issue><spage>1417</spage><epage>1432</epage><pages>1417-1432</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoacetonitriles. VIII were converted to 2-hydroxyimino-5-oxopiperazine derivatives (XV) and 5-oxo-2-thio-piperazines (XX). Preparations of N-(N-acylaminoacyl) aminoacetonitriles were also described. Further, N-α-hydroxyacylaminoacetonitriles were prepared from chloralides of α-hydroxyacids with aminoacetonitrile. 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subjects | Chemical and Drug Induced Liver Injury Lathyrism Nitriles - chemical synthesis |
title | Studies on Hepatic Agents. I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles |
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