Synthesis and GC-MS of 6-Alkylestradiols, Possible Aromatase Reaction Products of 6-Alkylandrostenediones
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概要
- 論文の詳細を見る
A series of 6α- and 6β-alkylestradiols (5 and 6) (alkyl : methyl, ethyl, n-propyl, n-pentyl, and n-heptyl) were synthesized as possible aromatase reaction products of 6-alkylandrost-4-ene-3,17-diones and their Δ^1-derivatives, potent competitive and mechanism-based inhibitors of aromatase. Treatment of 6-oxoestradiol with Grignard reagents followed by acid-catalyzed dehydration and subsequent catalytic hydrogenation over Pd-C gave the 6-alkylestradiols (5 and 6). GC-MS (electron impact mode) of trimethylsilyl derivatives of bis-trimethylsilyl derivatives of compounds 5 and 6 revealed that the 6α-alkyl compounds, 5,emerged with a longer retention time compared to the corresponding 6β-alkyl isomers, 6,where the retention time was in proportion to the length of the 6-alkyl chain in each series. In the MS, a molecular ion (M^+) peak was the base peak for all the 6-alkylestrogens, with strong and characteristic fragment ion peaks corresponding to M^+-131 and at m/z 325. A selected ion monitoring method using a molecular ion will be sensitive enough for analysis of the aromatization reaction of the 6-alkylandrogens.
- 社団法人日本薬学会の論文
- 1996-08-15
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
関連論文
- Synthesis and GC-MS of 6-Alkylestradiols, Possible Aromatase Reaction Products of 6-Alkylandrostenediones
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- Synthesis of 19-Oxygenated 4β, 5β-Epoxy Derivatives of 16α-Hydroxyandrostenedione as Mechanistic and Catalytic Probes for Aromatase Reaction
- C(10)-C(19) Bond Cleavage Reaction of 19-Oxygenated Androst-4-ene-3,6-dione Steroids under Various Conditions
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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
- 19-Oxygenation of C_-Steroids with an A, B-Ring Enone Structure, Competitive Inhibitors of Estrogen Biosynthesis, with Human Placental Aromatase
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