Synthesis and Hypoglycemic Activity of 7, 8-Dihydro-6H-thiopyrano[3, 2-d]pyrimidine Derivatives and Related Compounds
A series of 2-amino-7, 8-dihydro-4-piperazinyl- and 4-amino-7, 8-dihydro-2-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidines and related compounds were synthesized and evaluated for hypoglycemic activity. Several compounds exhibited excellent activity, and 7, 8-dihydro-2-(4-methyl-piperazinyl)-4-(1-pyrro...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1986/10/25, Vol.34(10), pp.4150-4165 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | OHNO, SACHIO MIZUKOSHI, KIYOSHI KOMATSU, OSAMU KUNOH, YASUO NAKAMURA, YOSHIKI KATOH, EIICHI NAGASAKA, MITSUAKI |
| description | A series of 2-amino-7, 8-dihydro-4-piperazinyl- and 4-amino-7, 8-dihydro-2-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidines and related compounds were synthesized and evaluated for hypoglycemic activity. Several compounds exhibited excellent activity, and 7, 8-dihydro-2-(4-methyl-piperazinyl)-4-(1-pyrrolidinyl)- (8c, dimaleate : MTP-1307) and 2-amino-7, 8-dihydro-4-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidine (18a, dimaleate : MTP-1403) were selected for further investigation.Oral administration of 8c and 18a at 50 mg/kg markedly improved oral glucose tolerance in ob/ob mice. In this test, buformin also showed activity, whereas tolbutamide produced no significant improvement. |
| doi_str_mv | 10.1248/cpb.34.4150 |
| format | Article |
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Several compounds exhibited excellent activity, and 7, 8-dihydro-2-(4-methyl-piperazinyl)-4-(1-pyrrolidinyl)- (8c, dimaleate : MTP-1307) and 2-amino-7, 8-dihydro-4-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidine (18a, dimaleate : MTP-1403) were selected for further investigation.Oral administration of 8c and 18a at 50 mg/kg markedly improved oral glucose tolerance in ob/ob mice. In this test, buformin also showed activity, whereas tolbutamide produced no significant improvement.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.34.4150</identifier><identifier>PMID: 3829149</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Chemical Phenomena ; Chemistry ; ciglitazone ; Exact sciences and technology ; Glucose Tolerance Test ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Hypoglycemic Agents - chemical synthesis ; Mice ; Mice, Obese ; Organic chemistry ; Piperazines - chemical synthesis ; Preparations and properties ; Pyrans - chemical synthesis ; Pyrimidines - chemical synthesis ; Rats</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1986/10/25, Vol.34(10), pp.4150-4165</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1987 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1986</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c668t-b61676b2c1f145a3aaca7aca5247dbf17aec7d3804ddc2c0e3016ac40f347fab3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,4022,27922,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8125980$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3829149$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>OHNO, SACHIO</creatorcontrib><creatorcontrib>MIZUKOSHI, KIYOSHI</creatorcontrib><creatorcontrib>KOMATSU, OSAMU</creatorcontrib><creatorcontrib>KUNOH, YASUO</creatorcontrib><creatorcontrib>NAKAMURA, YOSHIKI</creatorcontrib><creatorcontrib>KATOH, EIICHI</creatorcontrib><creatorcontrib>NAGASAKA, MITSUAKI</creatorcontrib><title>Synthesis and Hypoglycemic Activity of 7, 8-Dihydro-6H-thiopyrano[3, 2-d]pyrimidine Derivatives and Related Compounds</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of 2-amino-7, 8-dihydro-4-piperazinyl- and 4-amino-7, 8-dihydro-2-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidines and related compounds were synthesized and evaluated for hypoglycemic activity. Several compounds exhibited excellent activity, and 7, 8-dihydro-2-(4-methyl-piperazinyl)-4-(1-pyrrolidinyl)- (8c, dimaleate : MTP-1307) and 2-amino-7, 8-dihydro-4-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidine (18a, dimaleate : MTP-1403) were selected for further investigation.Oral administration of 8c and 18a at 50 mg/kg markedly improved oral glucose tolerance in ob/ob mice. In this test, buformin also showed activity, whereas tolbutamide produced no significant improvement.</description><subject>Animals</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>ciglitazone</subject><subject>Exact sciences and technology</subject><subject>Glucose Tolerance Test</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Hypoglycemic Agents - chemical synthesis</subject><subject>Mice</subject><subject>Mice, Obese</subject><subject>Organic chemistry</subject><subject>Piperazines - chemical synthesis</subject><subject>Preparations and properties</subject><subject>Pyrans - chemical synthesis</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Rats</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkd2L1DAUxYMo67j65LNQUHxxO-arSfq4zLqOsCD48SRSbpN0J0PbdJN2of-9KR1G8MWHJFzuL-cm5yD0muAtoVx91EO9ZXzLSYGfoA1hXOYFpewp2mCMy5wywZ6jFzEeMaYFluwCXTBFS8LLDZq-z_14sNHFDHqT7efB37eztp3T2bUe3aMb58w3mbzKVH7jDrMJPhf7fDw4P8wBev-LXWU0N79T5TpnXG-zGxvcI6TLdlX9ZlsYrcl2vhv81Jv4Ej1roI321em8RD9vP_3Y7fO7r5-_7K7vci2EGvNaECFFTTVpCC-AAWiQaRWUS1M3RILV0jCFuTGaamwZJgI0x03yoIGaXaL3q-4Q_MNk41h1LmrbttBbP8VKSqpkUYr_gskrQjiRCXz7D3j0U-jTJxIjMKGKlTRRH1ZKBx9jsE01JHMgzBXB1ZJZlTKrGK-WzBL95qQ51Z01Z_YUUuq_O_Uhamib5Lp28YwpQotSLTK3K3aMI9zbcx_C6HRrl5GkLNQyNr1i3Zf5f4EDhMr27A_x7Lb3</recordid><startdate>1986</startdate><enddate>1986</enddate><creator>OHNO, SACHIO</creator><creator>MIZUKOSHI, KIYOSHI</creator><creator>KOMATSU, OSAMU</creator><creator>KUNOH, YASUO</creator><creator>NAKAMURA, YOSHIKI</creator><creator>KATOH, EIICHI</creator><creator>NAGASAKA, MITSUAKI</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>1986</creationdate><title>Synthesis and Hypoglycemic Activity of 7, 8-Dihydro-6H-thiopyrano[3, 2-d]pyrimidine Derivatives and Related Compounds</title><author>OHNO, SACHIO ; MIZUKOSHI, KIYOSHI ; KOMATSU, OSAMU ; KUNOH, YASUO ; NAKAMURA, YOSHIKI ; KATOH, EIICHI ; NAGASAKA, MITSUAKI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c668t-b61676b2c1f145a3aaca7aca5247dbf17aec7d3804ddc2c0e3016ac40f347fab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Animals</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>ciglitazone</topic><topic>Exact sciences and technology</topic><topic>Glucose Tolerance Test</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Hypoglycemic Agents - chemical synthesis</topic><topic>Mice</topic><topic>Mice, Obese</topic><topic>Organic chemistry</topic><topic>Piperazines - chemical synthesis</topic><topic>Preparations and properties</topic><topic>Pyrans - chemical synthesis</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Rats</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>OHNO, SACHIO</creatorcontrib><creatorcontrib>MIZUKOSHI, KIYOSHI</creatorcontrib><creatorcontrib>KOMATSU, OSAMU</creatorcontrib><creatorcontrib>KUNOH, YASUO</creatorcontrib><creatorcontrib>NAKAMURA, YOSHIKI</creatorcontrib><creatorcontrib>KATOH, EIICHI</creatorcontrib><creatorcontrib>NAGASAKA, MITSUAKI</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>OHNO, SACHIO</au><au>MIZUKOSHI, KIYOSHI</au><au>KOMATSU, OSAMU</au><au>KUNOH, YASUO</au><au>NAKAMURA, YOSHIKI</au><au>KATOH, EIICHI</au><au>NAGASAKA, MITSUAKI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Hypoglycemic Activity of 7, 8-Dihydro-6H-thiopyrano[3, 2-d]pyrimidine Derivatives and Related Compounds</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1986</date><risdate>1986</risdate><volume>34</volume><issue>10</issue><spage>4150</spage><epage>4165</epage><pages>4150-4165</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>A series of 2-amino-7, 8-dihydro-4-piperazinyl- and 4-amino-7, 8-dihydro-2-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidines and related compounds were synthesized and evaluated for hypoglycemic activity. Several compounds exhibited excellent activity, and 7, 8-dihydro-2-(4-methyl-piperazinyl)-4-(1-pyrrolidinyl)- (8c, dimaleate : MTP-1307) and 2-amino-7, 8-dihydro-4-piperazinyl-6H-thiopyrano[3, 2-d]pyrimidine (18a, dimaleate : MTP-1403) were selected for further investigation.Oral administration of 8c and 18a at 50 mg/kg markedly improved oral glucose tolerance in ob/ob mice. In this test, buformin also showed activity, whereas tolbutamide produced no significant improvement.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>3829149</pmid><doi>10.1248/cpb.34.4150</doi><tpages>16</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Chemical Phenomena Chemistry ciglitazone Exact sciences and technology Glucose Tolerance Test Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Hypoglycemic Agents - chemical synthesis Mice Mice, Obese Organic chemistry Piperazines - chemical synthesis Preparations and properties Pyrans - chemical synthesis Pyrimidines - chemical synthesis Rats |
| title | Synthesis and Hypoglycemic Activity of 7, 8-Dihydro-6H-thiopyrano[3, 2-d]pyrimidine Derivatives and Related Compounds |
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