An Effective Synthesis of 5,4′-Disubstituted Flavones via a Cesium Enolate Assisted Intramolecular ipso-Substitution Reaction

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
Hauptverfasser: Matsugi, Masato, Takeda, Masaki, Takahashi, Ayano, Tazaki, Takahide, Tamura, Hiroto, Shioiri, Takayuki
Format: Artikel
Sprache:eng
Schlagworte:
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
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Zusammenfassung: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.58.1107