Synthesis and Bioactivity of Propranolol Analogues with a Rigid Skeleton. I
The synthesis of two kinds of propranolol analogues, A and B, with a rigid skeleton was investigated. The compounds were designed to help identify the conformation involved in β-adrenergic receptor-propranolol interaction. The key intermediate, 2-hydroxy·2, 3-dihydronaphtho[1, 8-bc]pyran (5), was ob...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1990/12/25, Vol.38(12), pp.3257-3260 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | MIKI, Yasuyoshi HACHIKEN, Hiroko NOGUCHI, Koji OHTA, Mayumi NAKANO, Akiko TAKAHASHI, Koichi TAKEMURA, Shoji |
| description | The synthesis of two kinds of propranolol analogues, A and B, with a rigid skeleton was investigated. The compounds were designed to help identify the conformation involved in β-adrenergic receptor-propranolol interaction. The key intermediate, 2-hydroxy·2, 3-dihydronaphtho[1, 8-bc]pyran (5), was obtained starting from acenaphthenone (1). On sequential dehydration, hydroboration, and oxidation, 5 gave 2, 3-dihydronaphtho[1, 8-bc]pyran-3-one (8), which was converted to compound A. Compound 5 was also derived to 2-formyl-2, 3-dihydronaphtho[1, 8-bc]pyran (13) via the 2-vinyl compound (12). Condensation of nitromethane with 13 followed by reduction and alkylation produced the desired compound B. The β-blocking activities of A and B were examined. |
| doi_str_mv | 10.1248/cpb.38.3257 |
| format | Article |
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I</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>MIKI, Yasuyoshi ; HACHIKEN, Hiroko ; NOGUCHI, Koji ; OHTA, Mayumi ; NAKANO, Akiko ; TAKAHASHI, Koichi ; TAKEMURA, Shoji</creator><creatorcontrib>MIKI, Yasuyoshi ; HACHIKEN, Hiroko ; NOGUCHI, Koji ; OHTA, Mayumi ; NAKANO, Akiko ; TAKAHASHI, Koichi ; TAKEMURA, Shoji</creatorcontrib><description>The synthesis of two kinds of propranolol analogues, A and B, with a rigid skeleton was investigated. The compounds were designed to help identify the conformation involved in β-adrenergic receptor-propranolol interaction. The key intermediate, 2-hydroxy·2, 3-dihydronaphtho[1, 8-bc]pyran (5), was obtained starting from acenaphthenone (1). On sequential dehydration, hydroboration, and oxidation, 5 gave 2, 3-dihydronaphtho[1, 8-bc]pyran-3-one (8), which was converted to compound A. Compound 5 was also derived to 2-formyl-2, 3-dihydronaphtho[1, 8-bc]pyran (13) via the 2-vinyl compound (12). Condensation of nitromethane with 13 followed by reduction and alkylation produced the desired compound B. The β-blocking activities of A and B were examined.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.38.3257</identifier><identifier>PMID: 1982645</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Adrenergic beta-Antagonists - chemical synthesis ; Animals ; Chemistry ; dihydronaphtho[1, 8-bc]pyran derivative ; drug design ; Exact sciences and technology ; Guinea Pigs ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; In Vitro Techniques ; Male ; Molecular Conformation ; Myocardial Contraction - drug effects ; Organic chemistry ; Preparations and properties ; Propranolol - analogs & derivatives ; Propranolol - pharmacology ; propranolol analogue ; β-adrenergic agent ; β-blocking activity</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1990/12/25, Vol.38(12), pp.3257-3260</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1991 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1990</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-cda53a649da644d0b556d559619beeb7548926000dc66ea23612ad2676fbda4d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19730954$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1982645$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>MIKI, Yasuyoshi</creatorcontrib><creatorcontrib>HACHIKEN, Hiroko</creatorcontrib><creatorcontrib>NOGUCHI, Koji</creatorcontrib><creatorcontrib>OHTA, Mayumi</creatorcontrib><creatorcontrib>NAKANO, Akiko</creatorcontrib><creatorcontrib>TAKAHASHI, Koichi</creatorcontrib><creatorcontrib>TAKEMURA, Shoji</creatorcontrib><title>Synthesis and Bioactivity of Propranolol Analogues with a Rigid Skeleton. I</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The synthesis of two kinds of propranolol analogues, A and B, with a rigid skeleton was investigated. The compounds were designed to help identify the conformation involved in β-adrenergic receptor-propranolol interaction. The key intermediate, 2-hydroxy·2, 3-dihydronaphtho[1, 8-bc]pyran (5), was obtained starting from acenaphthenone (1). On sequential dehydration, hydroboration, and oxidation, 5 gave 2, 3-dihydronaphtho[1, 8-bc]pyran-3-one (8), which was converted to compound A. Compound 5 was also derived to 2-formyl-2, 3-dihydronaphtho[1, 8-bc]pyran (13) via the 2-vinyl compound (12). Condensation of nitromethane with 13 followed by reduction and alkylation produced the desired compound B. The β-blocking activities of A and B were examined.</description><subject>Adrenergic beta-Antagonists - chemical synthesis</subject><subject>Animals</subject><subject>Chemistry</subject><subject>dihydronaphtho[1, 8-bc]pyran derivative</subject><subject>drug design</subject><subject>Exact sciences and technology</subject><subject>Guinea Pigs</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>In Vitro Techniques</subject><subject>Male</subject><subject>Molecular Conformation</subject><subject>Myocardial Contraction - drug effects</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Propranolol - analogs & derivatives</subject><subject>Propranolol - pharmacology</subject><subject>propranolol analogue</subject><subject>β-adrenergic agent</subject><subject>β-blocking activity</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkE1vEzEQhi1EVULhxBnJEoIL2uDvXR9LRaFqJRCFszVrexOHzTq1HVD-PY4SWtTLzGEezbzzIPSKkjllovtgN_2cd3POZPsEzSgXbSMZ40_RjBCiG8YVf4ae57wihEnS8lN0SnXHlJAzdH27m8rS55AxTA5_DBFsCb9D2eE44G8pbhJMcYwjPp9gjIutz_hPKEsM-HtYBIdvf_nRlzjN8dULdDLAmP3LYz9DPy8__bj40tx8_Xx1cX7TWEFlaawDyUEJ7WoRjvRSKielVlT33vetFJ1mqkZ3VikPNT5l4Jhq1dA7EI6foXeHvZsU72qgYtYhWz-OMPm4zaYjnLNOywq-eQSu4jbVP7KhQhHGuRBtpd4fKJtizskPZpPCGtLOUGL2gk0VbHhn9oIr_fq4c9uvvXtgD0br_O1xDtnCOFR9NuT_sJYTLUXlLg_cKhdY-HsAUgl29PubVMtuf5eyf7UGeACWkIyf-F9PzJn1</recordid><startdate>199012</startdate><enddate>199012</enddate><creator>MIKI, Yasuyoshi</creator><creator>HACHIKEN, Hiroko</creator><creator>NOGUCHI, Koji</creator><creator>OHTA, Mayumi</creator><creator>NAKANO, Akiko</creator><creator>TAKAHASHI, Koichi</creator><creator>TAKEMURA, Shoji</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>199012</creationdate><title>Synthesis and Bioactivity of Propranolol Analogues with a Rigid Skeleton. I</title><author>MIKI, Yasuyoshi ; HACHIKEN, Hiroko ; NOGUCHI, Koji ; OHTA, Mayumi ; NAKANO, Akiko ; TAKAHASHI, Koichi ; TAKEMURA, Shoji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-cda53a649da644d0b556d559619beeb7548926000dc66ea23612ad2676fbda4d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>Adrenergic beta-Antagonists - chemical synthesis</topic><topic>Animals</topic><topic>Chemistry</topic><topic>dihydronaphtho[1, 8-bc]pyran derivative</topic><topic>drug design</topic><topic>Exact sciences and technology</topic><topic>Guinea Pigs</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>In Vitro Techniques</topic><topic>Male</topic><topic>Molecular Conformation</topic><topic>Myocardial Contraction - drug effects</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Propranolol - analogs & derivatives</topic><topic>Propranolol - pharmacology</topic><topic>propranolol analogue</topic><topic>β-adrenergic agent</topic><topic>β-blocking activity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>MIKI, Yasuyoshi</creatorcontrib><creatorcontrib>HACHIKEN, Hiroko</creatorcontrib><creatorcontrib>NOGUCHI, Koji</creatorcontrib><creatorcontrib>OHTA, Mayumi</creatorcontrib><creatorcontrib>NAKANO, Akiko</creatorcontrib><creatorcontrib>TAKAHASHI, Koichi</creatorcontrib><creatorcontrib>TAKEMURA, Shoji</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>MIKI, Yasuyoshi</au><au>HACHIKEN, Hiroko</au><au>NOGUCHI, Koji</au><au>OHTA, Mayumi</au><au>NAKANO, Akiko</au><au>TAKAHASHI, Koichi</au><au>TAKEMURA, Shoji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Bioactivity of Propranolol Analogues with a Rigid Skeleton. I</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1990-12</date><risdate>1990</risdate><volume>38</volume><issue>12</issue><spage>3257</spage><epage>3260</epage><pages>3257-3260</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>The synthesis of two kinds of propranolol analogues, A and B, with a rigid skeleton was investigated. The compounds were designed to help identify the conformation involved in β-adrenergic receptor-propranolol interaction. The key intermediate, 2-hydroxy·2, 3-dihydronaphtho[1, 8-bc]pyran (5), was obtained starting from acenaphthenone (1). On sequential dehydration, hydroboration, and oxidation, 5 gave 2, 3-dihydronaphtho[1, 8-bc]pyran-3-one (8), which was converted to compound A. Compound 5 was also derived to 2-formyl-2, 3-dihydronaphtho[1, 8-bc]pyran (13) via the 2-vinyl compound (12). Condensation of nitromethane with 13 followed by reduction and alkylation produced the desired compound B. The β-blocking activities of A and B were examined.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>1982645</pmid><doi>10.1248/cpb.38.3257</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Adrenergic beta-Antagonists - chemical synthesis Animals Chemistry dihydronaphtho[1, 8-bc]pyran derivative drug design Exact sciences and technology Guinea Pigs Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives In Vitro Techniques Male Molecular Conformation Myocardial Contraction - drug effects Organic chemistry Preparations and properties Propranolol - analogs & derivatives Propranolol - pharmacology propranolol analogue β-adrenergic agent β-blocking activity |
| title | Synthesis and Bioactivity of Propranolol Analogues with a Rigid Skeleton. I |
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