Synthesis of 19-Oxygenated 4β, 5β-Epoxy Derivatives of 16α-Hydroxyandrostenedione as Mechanistic and Catalytic Probes for Aromatase Reaction
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概要
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4β, 5β-Epoxy derivatives of 16α-hydroxyandrostenedione (2), one of the natural substrates for aromatase, and its 19-oxygenated compounds 4 and 5 were synthesized as mechanistic and catalytic probes for the enzyme reaction. Treatment of 16α-bromoandrostenedione (13) or its 19-hydroxy analog 19 which was prepared from 3β-hydroxy-19-(tert-butyldimethylsiloxy)androst-5-en-17-one (16) in three steps, with H_2O_2 and NaOH followed by controlled alkaline hydrolysis with NaOH in aqueous pyridine stereospecifically yielded 4β, 5β-epoxy-16α-ol 15 or 4β, 5β-epoxy-16α, 19-diol 22,respectively. Oxidation of 16β-bromo-4β, 5β-epoxy-19-ol 21 with pyridinium dichromate followed by controlled alkaline hydrolysis produced 4β, 5β-epoxy-16α-hydroxy-19-al 24.
- 社団法人日本薬学会の論文
- 2000-09-01
著者
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Yoshimura Akiko
Tohoku Pharmaceutical University
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Yoshimura Akiko
Tohoku College Of Pharmacy
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NUMAZAWA Mitsuteru
Tohoku College of Pharmacy
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Numazawa Mitsuteru
Tohoku Pharmaceutical University
関連論文
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- Synthesis and Biochemical Studies of 19-Oxygenated Derivatives of 6α- and 6β-Methylandrostenediones as Catalytic Probes for the Active Site of Aromatase
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