Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1, 4-Dihydro-3, 5-pyridinedicarboxylates Leading to Optically Active Medicines
Chiral 4-aryl-1, 4-dihydro-2, 6-dimethyl-3, 5-pyridinedicarboxylates and 1, 4-dihydro-2, 4, 6-trimethyl-3, 5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase-catalyzed hydrolysis of bis(acyloxymethyl) 1, 4-dihydro-3, 5-pyridinedicarboxylate in an H2O/organic solvent system. These chira...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1997/05/15, Vol.45(5), pp.863-868 |
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| creator | EBIIKE, Hirosato MARUYAMA, Kaori YAMAZAKI, Yukiyoshi HIROSE, Yoshihiko KARIYA, Kinya SASAKI, Ikuharu KURONO, Yoshiaki TERAO, Yoshiyasu ACHIWA, Kazuo |
| description | Chiral 4-aryl-1, 4-dihydro-2, 6-dimethyl-3, 5-pyridinedicarboxylates and 1, 4-dihydro-2, 4, 6-trimethyl-3, 5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase-catalyzed hydrolysis of bis(acyloxymethyl) 1, 4-dihydro-3, 5-pyridinedicarboxylate in an H2O/organic solvent system. These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248. |
| doi_str_mv | 10.1248/cpb.45.863 |
| format | Article |
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These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.45.863</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>1, 4-dihydropyridine ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; calcium antagonist ; Chemistry ; Exact sciences and technology ; Fundamental and applied biological sciences. Psychology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; lipase-catalyzed reaction ; Methods. Procedures. Technologies ; Organic chemistry ; Preparations and properties</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1997/05/15, Vol.45(5), pp.863-868</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1997 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1997</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c574t-fccd69da388a57cdfab4c75726bbb769ff1ef867ce3ea86baa179363cbbe1a0d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27902,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2716041$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>EBIIKE, Hirosato</creatorcontrib><creatorcontrib>MARUYAMA, Kaori</creatorcontrib><creatorcontrib>YAMAZAKI, Yukiyoshi</creatorcontrib><creatorcontrib>HIROSE, Yoshihiko</creatorcontrib><creatorcontrib>KARIYA, Kinya</creatorcontrib><creatorcontrib>SASAKI, Ikuharu</creatorcontrib><creatorcontrib>KURONO, Yoshiaki</creatorcontrib><creatorcontrib>TERAO, Yoshiyasu</creatorcontrib><creatorcontrib>ACHIWA, Kazuo</creatorcontrib><title>Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1, 4-Dihydro-3, 5-pyridinedicarboxylates Leading to Optically Active Medicines</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Chiral 4-aryl-1, 4-dihydro-2, 6-dimethyl-3, 5-pyridinedicarboxylates and 1, 4-dihydro-2, 4, 6-trimethyl-3, 5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase-catalyzed hydrolysis of bis(acyloxymethyl) 1, 4-dihydro-3, 5-pyridinedicarboxylate in an H2O/organic solvent system. These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248.</description><subject>1, 4-dihydropyridine</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>calcium antagonist</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>lipase-catalyzed reaction</subject><subject>Methods. Procedures. Technologies</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>1997</creationdate><recordtype>article</recordtype><recordid>eNpFkMFu1DAQhiNEJZaWC09gCQ6AmsWO7Tg5tkuhlRb1Audo4oy7XrlJsF2E-xa8MY5SlcuMNP83_2j-onjL6JZVovms534r5Lap-Ytiw7hQpawq_rLYUErbsuI1f1W8DuFIaSWp4pvi797OELDcQQSXHnEgVyOM0U4BHepofyO5ToOfXAo2kMmQSxs-gE5u-pPuMR6S-0jYORHlF3tYuJKfE1nOydvBjjhYDb7PqIOIgewR8vSOxInczjFrziVysV75vsB5JZwVJwZcwDdP_bT4-fXqx-663N9-u9ld7EstlYil0Xqo2wF404BUejDQC62kquq-71XdGsPQNLXSyBGaugdgqs3_675HBnTgp8W71Xf2068HDLE7Tg9-zCc7JmrKGRUtzdSnldJ-CsGj6WZv78GnjtFuibzLkXdCdjnyDL9_soSQnzMeRm3D80alWE0Fy9huxY4hwh0-6-BzJg4XR9bKZnGVa8nm_9UD-A5H_g9A6pv7</recordid><startdate>1997</startdate><enddate>1997</enddate><creator>EBIIKE, Hirosato</creator><creator>MARUYAMA, Kaori</creator><creator>YAMAZAKI, Yukiyoshi</creator><creator>HIROSE, Yoshihiko</creator><creator>KARIYA, Kinya</creator><creator>SASAKI, Ikuharu</creator><creator>KURONO, Yoshiaki</creator><creator>TERAO, Yoshiyasu</creator><creator>ACHIWA, Kazuo</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>1997</creationdate><title>Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1, 4-Dihydro-3, 5-pyridinedicarboxylates Leading to Optically Active Medicines</title><author>EBIIKE, Hirosato ; MARUYAMA, Kaori ; YAMAZAKI, Yukiyoshi ; HIROSE, Yoshihiko ; KARIYA, Kinya ; SASAKI, Ikuharu ; KURONO, Yoshiaki ; TERAO, Yoshiyasu ; ACHIWA, Kazuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c574t-fccd69da388a57cdfab4c75726bbb769ff1ef867ce3ea86baa179363cbbe1a0d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>1, 4-dihydropyridine</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>calcium antagonist</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>lipase-catalyzed reaction</topic><topic>Methods. Procedures. Technologies</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>EBIIKE, Hirosato</creatorcontrib><creatorcontrib>MARUYAMA, Kaori</creatorcontrib><creatorcontrib>YAMAZAKI, Yukiyoshi</creatorcontrib><creatorcontrib>HIROSE, Yoshihiko</creatorcontrib><creatorcontrib>KARIYA, Kinya</creatorcontrib><creatorcontrib>SASAKI, Ikuharu</creatorcontrib><creatorcontrib>KURONO, Yoshiaki</creatorcontrib><creatorcontrib>TERAO, Yoshiyasu</creatorcontrib><creatorcontrib>ACHIWA, Kazuo</creatorcontrib><collection>Pascal-Francis</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><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>EBIIKE, Hirosato</au><au>MARUYAMA, Kaori</au><au>YAMAZAKI, Yukiyoshi</au><au>HIROSE, Yoshihiko</au><au>KARIYA, Kinya</au><au>SASAKI, Ikuharu</au><au>KURONO, Yoshiaki</au><au>TERAO, Yoshiyasu</au><au>ACHIWA, Kazuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1, 4-Dihydro-3, 5-pyridinedicarboxylates Leading to Optically Active Medicines</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1997</date><risdate>1997</risdate><volume>45</volume><issue>5</issue><spage>863</spage><epage>868</epage><pages>863-868</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Chiral 4-aryl-1, 4-dihydro-2, 6-dimethyl-3, 5-pyridinedicarboxylates and 1, 4-dihydro-2, 4, 6-trimethyl-3, 5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase-catalyzed hydrolysis of bis(acyloxymethyl) 1, 4-dihydro-3, 5-pyridinedicarboxylate in an H2O/organic solvent system. These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.45.863</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 1, 4-dihydropyridine Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology calcium antagonist Chemistry Exact sciences and technology Fundamental and applied biological sciences. Psychology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives lipase-catalyzed reaction Methods. Procedures. Technologies Organic chemistry Preparations and properties |
| title | Lipase-Catalyzed Enantioselective Hydrolysis of Bis(acyloxymethyl) 1, 4-Dihydro-3, 5-pyridinedicarboxylates Leading to Optically Active Medicines |
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