Synthesis of 3-Ureido Derivatives of Coumarin and 2-Quinolone as Potent Acyl-CoA : Cholesterol Acyltransferase Inhibitors
Novel 3-ureido derivatives of 4-phenylcoumarin and 4-phenyl-2-quinolone were synthesized and evaluated for acyl-CoA : cholesterol acyltransferase (ACAT)-inhibitory activity. These derivatives inhibited rat intestinal ACAT with IC50 values at the 10-8 to 10-9 M level and were found to normalize plasm...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1995/04/15, Vol.43(4), pp.616-625 |
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| container_end_page | 625 |
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| container_issue | 4 |
| container_start_page | 616 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 43 |
| creator | TAWADA, Hiroyuki NATSUGARI, Hideaki ISHIKAWA, Eiichiro SUGIYAMA, Yasuo IKEDA, Hitoshi MEGURO, Kanji |
| description | Novel 3-ureido derivatives of 4-phenylcoumarin and 4-phenyl-2-quinolone were synthesized and evaluated for acyl-CoA : cholesterol acyltransferase (ACAT)-inhibitory activity. These derivatives inhibited rat intestinal ACAT with IC50 values at the 10-8 to 10-9 M level and were found to normalize plasma cholesterol levels in cholesterol-fed rats when administered as dietary admixtures. |
| doi_str_mv | 10.1248/cpb.43.616 |
| format | Article |
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These derivatives inhibited rat intestinal ACAT with IC50 values at the 10-8 to 10-9 M level and were found to normalize plasma cholesterol levels in cholesterol-fed rats when administered as dietary admixtures.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.43.616</identifier><identifier>PMID: 7600615</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>ACAT inhibitor ; Animals ; antiatherosclerotic agent ; Biological and medical sciences ; cholesterol esterification ; Coumarins - chemical synthesis ; Coumarins - chemistry ; Coumarins - pharmacology ; General and cellular metabolism. Vitamins ; hypocholesterolemic effect ; Hypolipidemic Agents - pharmacology ; In Vitro Techniques ; Magnetic Resonance Spectroscopy ; Male ; Medical sciences ; Pharmacology. Drug treatments ; Quinolones - chemical synthesis ; Quinolones - chemistry ; Quinolones - pharmacology ; Rats ; Rats, Sprague-Dawley ; Sterol O-Acyltransferase - antagonists & inhibitors ; ureidocoumarin ; ureidoquinolone</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1995/04/15, Vol.43(4), pp.616-625</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c603t-d7d9176e31f133bdb9a09ff10ecb76d52e62af1d7e97504d7415a85897ffffb63</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,4009,27902,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3578624$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7600615$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>TAWADA, Hiroyuki</creatorcontrib><creatorcontrib>NATSUGARI, Hideaki</creatorcontrib><creatorcontrib>ISHIKAWA, Eiichiro</creatorcontrib><creatorcontrib>SUGIYAMA, Yasuo</creatorcontrib><creatorcontrib>IKEDA, Hitoshi</creatorcontrib><creatorcontrib>MEGURO, Kanji</creatorcontrib><title>Synthesis of 3-Ureido Derivatives of Coumarin and 2-Quinolone as Potent Acyl-CoA : Cholesterol Acyltransferase Inhibitors</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Novel 3-ureido derivatives of 4-phenylcoumarin and 4-phenyl-2-quinolone were synthesized and evaluated for acyl-CoA : cholesterol acyltransferase (ACAT)-inhibitory activity. These derivatives inhibited rat intestinal ACAT with IC50 values at the 10-8 to 10-9 M level and were found to normalize plasma cholesterol levels in cholesterol-fed rats when administered as dietary admixtures.</description><subject>ACAT inhibitor</subject><subject>Animals</subject><subject>antiatherosclerotic agent</subject><subject>Biological and medical sciences</subject><subject>cholesterol esterification</subject><subject>Coumarins - chemical synthesis</subject><subject>Coumarins - chemistry</subject><subject>Coumarins - pharmacology</subject><subject>General and cellular metabolism. Vitamins</subject><subject>hypocholesterolemic effect</subject><subject>Hypolipidemic Agents - pharmacology</subject><subject>In Vitro Techniques</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinolones - chemical synthesis</subject><subject>Quinolones - chemistry</subject><subject>Quinolones - pharmacology</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Sterol O-Acyltransferase - antagonists & inhibitors</subject><subject>ureidocoumarin</subject><subject>ureidoquinolone</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkM2LFDEQxYMo67h68S7kIB6EHpNOJ-n2NrRfCwsquueQ7lScLJlkTNIL89-b2RnGHCpQ70e9qofQa0rWtO36D_N-WndsLah4glaUdbLhbcueohUhZGhaJthz9CLne0JaTiS7QldSECIoX6HDr0MoW8gu42gxa-4SOBPxJ0juQRf3AI_9MS47nVzAOhjcNj8XF6KPAbDO-EcsEArezAffjHGDP-JxGz3kAin6x3ZJOmQLSWfAN2HrJldiyi_RM6t9hlfn_xrdffn8e_zW3H7_ejNubptZEFYaI81ApQBGLWVsMtOgyWAtJTBPUhjegmi1pUbCIDnpjOwo1z3vB2nrmwS7Ru9Oc_cp_l3qXmrn8gze6wBxyUpKJmnPaAXfn8A5xZwTWLVPrp59UJSoY86q5qw6pmrOFX5znrpMOzAX9Bxs1d-edZ1n7W2NYHb5gjEue9F2FRtP2H0u-g9cdJ2Kmz0cHenA-6NrdyrV_L-61UlBYP8A8D6eCg</recordid><startdate>1995</startdate><enddate>1995</enddate><creator>TAWADA, Hiroyuki</creator><creator>NATSUGARI, Hideaki</creator><creator>ISHIKAWA, Eiichiro</creator><creator>SUGIYAMA, Yasuo</creator><creator>IKEDA, Hitoshi</creator><creator>MEGURO, Kanji</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</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>7X8</scope></search><sort><creationdate>1995</creationdate><title>Synthesis of 3-Ureido Derivatives of Coumarin and 2-Quinolone as Potent Acyl-CoA : Cholesterol Acyltransferase Inhibitors</title><author>TAWADA, Hiroyuki ; NATSUGARI, Hideaki ; ISHIKAWA, Eiichiro ; SUGIYAMA, Yasuo ; IKEDA, Hitoshi ; MEGURO, Kanji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c603t-d7d9176e31f133bdb9a09ff10ecb76d52e62af1d7e97504d7415a85897ffffb63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>ACAT inhibitor</topic><topic>Animals</topic><topic>antiatherosclerotic agent</topic><topic>Biological and medical sciences</topic><topic>cholesterol esterification</topic><topic>Coumarins - chemical synthesis</topic><topic>Coumarins - chemistry</topic><topic>Coumarins - pharmacology</topic><topic>General and cellular metabolism. Vitamins</topic><topic>hypocholesterolemic effect</topic><topic>Hypolipidemic Agents - pharmacology</topic><topic>In Vitro Techniques</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinolones - chemical synthesis</topic><topic>Quinolones - chemistry</topic><topic>Quinolones - pharmacology</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Sterol O-Acyltransferase - antagonists & inhibitors</topic><topic>ureidocoumarin</topic><topic>ureidoquinolone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>TAWADA, Hiroyuki</creatorcontrib><creatorcontrib>NATSUGARI, Hideaki</creatorcontrib><creatorcontrib>ISHIKAWA, Eiichiro</creatorcontrib><creatorcontrib>SUGIYAMA, Yasuo</creatorcontrib><creatorcontrib>IKEDA, Hitoshi</creatorcontrib><creatorcontrib>MEGURO, Kanji</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>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>TAWADA, Hiroyuki</au><au>NATSUGARI, Hideaki</au><au>ISHIKAWA, Eiichiro</au><au>SUGIYAMA, Yasuo</au><au>IKEDA, Hitoshi</au><au>MEGURO, Kanji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3-Ureido Derivatives of Coumarin and 2-Quinolone as Potent Acyl-CoA : Cholesterol Acyltransferase Inhibitors</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1995</date><risdate>1995</risdate><volume>43</volume><issue>4</issue><spage>616</spage><epage>625</epage><pages>616-625</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Novel 3-ureido derivatives of 4-phenylcoumarin and 4-phenyl-2-quinolone were synthesized and evaluated for acyl-CoA : cholesterol acyltransferase (ACAT)-inhibitory activity. These derivatives inhibited rat intestinal ACAT with IC50 values at the 10-8 to 10-9 M level and were found to normalize plasma cholesterol levels in cholesterol-fed rats when administered as dietary admixtures.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>7600615</pmid><doi>10.1248/cpb.43.616</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1995/04/15, Vol.43(4), pp.616-625 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_77371831 |
| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| subjects | ACAT inhibitor Animals antiatherosclerotic agent Biological and medical sciences cholesterol esterification Coumarins - chemical synthesis Coumarins - chemistry Coumarins - pharmacology General and cellular metabolism. Vitamins hypocholesterolemic effect Hypolipidemic Agents - pharmacology In Vitro Techniques Magnetic Resonance Spectroscopy Male Medical sciences Pharmacology. Drug treatments Quinolones - chemical synthesis Quinolones - chemistry Quinolones - pharmacology Rats Rats, Sprague-Dawley Sterol O-Acyltransferase - antagonists & inhibitors ureidocoumarin ureidoquinolone |
| title | Synthesis of 3-Ureido Derivatives of Coumarin and 2-Quinolone as Potent Acyl-CoA : Cholesterol Acyltransferase Inhibitors |
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