An Effective Synthesis of 5,4′-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction
A variety of 5,4′-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and variou...
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2010/08/01, Vol.58(8), pp.1107-1110 |
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| container_end_page | 1110 |
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| container_issue | 8 |
| container_start_page | 1107 |
| container_title | Chemical & Pharmaceutical Bulletin |
| container_volume | 58 |
| creator | Matsugi, Masato Takeda, Masaki Takahashi, Ayano Tazaki, Takahide Tamura, Hiroto Shioiri, Takayuki |
| description | A variety of 5,4′-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and various benzoyl chlorides was effective in the preparation of 5-hydroxy-4′-alkylflavones. |
| doi_str_mv | 10.1248/cpb.58.1107 |
| format | Article |
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It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and various benzoyl chlorides was effective in the preparation of 5-hydroxy-4′-alkylflavones.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.58.1107</identifier><identifier>PMID: 20686270</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>androgen ; Androgen Receptor Antagonists - chemical synthesis ; Androgen Receptor Antagonists - chemistry ; antagonist ; Cesium - chemistry ; flavone ; Flavones - chemical synthesis ; Flavones - chemistry ; Flavones - pharmacology ; ipso-substitution ; Molecular Structure ; Stereoisomerism</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2010/08/01, Vol.58(8), pp.1107-1110</ispartof><rights>2010 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c667t-bf93d5604a8db74ac0c7bf23b90e6f12b27847b69eae28d6f79da9a4632afc3e3</citedby><cites>FETCH-LOGICAL-c667t-bf93d5604a8db74ac0c7bf23b90e6f12b27847b69eae28d6f79da9a4632afc3e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20686270$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Matsugi, Masato</creatorcontrib><creatorcontrib>Takeda, Masaki</creatorcontrib><creatorcontrib>Takahashi, Ayano</creatorcontrib><creatorcontrib>Tazaki, Takahide</creatorcontrib><creatorcontrib>Tamura, Hiroto</creatorcontrib><creatorcontrib>Shioiri, Takayuki</creatorcontrib><creatorcontrib>Department of Applied Biological Chemistry</creatorcontrib><creatorcontrib>Meijo University</creatorcontrib><creatorcontrib>Faculty of Agriculture</creatorcontrib><title>An Effective Synthesis of 5,4′-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction</title><title>Chemical & Pharmaceutical Bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A variety of 5,4′-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. 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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2010/08/01, Vol.58(8), pp.1107-1110 |
| issn | 0009-2363 1347-5223 |
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| source | J-STAGE (Free - Japanese); MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | androgen Androgen Receptor Antagonists - chemical synthesis Androgen Receptor Antagonists - chemistry antagonist Cesium - chemistry flavone Flavones - chemical synthesis Flavones - chemistry Flavones - pharmacology ipso-substitution Molecular Structure Stereoisomerism |
| title | An Effective Synthesis of 5,4′-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction |
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