Synthesis of Deuterium-Labelled 16α-Hydroxy-4-androstene-3,17-dione and 16α-Hydroxydehydroepiandrosterone
スポンサーリンク
概要
- 論文の詳細を見る
16α-Hydroxy-4-androstene-3,17-dione-d_5 (4) and 3β, 16α-dihydroxy-5-androsten-17-one-d_6 (10) were synthesized. Treatment of 16α-bromo-5-androstene-3,17-dione (2) with deuterium oxide and methanol-OD gave the 4-en-3-oxo derivative-d 3. The bromide 3 was converted into the 16α-hydroxide-d_5 4 via controlled alkaline hydrolysis using sodium hydroxide-OD in deuterium oxide-pyridine. 3β-Hydroxy-5-androsten-17-one-d_5 (8), which was obtained from 17,17-ethylenedioxy-5-androsten-3-one (5) via treatment with potassium tert-butoxide in tert-butanol-OD, followed by lithium aluminum tri-tert-butoxydeuteride reduction and then acid hydrolysis, was derivatized to the 16α-bromide 9 by treatment with cupric bromide. The bromide 9 was similarly hydrolyzed to yield the 16α-hydroxide-d_6 10.
- 公益社団法人日本薬学会の論文
- 1985-02-25
著者
-
沼沢 光輝
Tohoku Pharmaceutical University
-
沼沢 光輝
Tohoku College Of Pharmacy
-
尾形 美恵子
Tohoku College of Pharmacy
関連論文
- アロマターゼの自殺基質ATとシステインとの反応性
- Conformational Analysis of 19-Oxygenated Steroids with a 4-Ene or 2,4-Diene Structure, Potential Intermediates of Aromatase Reaction, with Semiempirical Molecular Orbital PM3 Calculations
- C(10)-C(19) Bond Cleavage Reaction of 19-Oxygenated Androst-4-ene-3,6-dione Steroids under Various Conditions
- Improved Synthesis and Molecular Modeling of 4β,19-Dihydroxyandrost-5-en-17-one, an Excellent Inhibitor of Aromatase
- Androst-4-ene-17-thione とその 5-ene 異性体の合成とアロマターゼ阻害活性
- Aromatization of 19-Oxygenated Androst-4-ene-3,6,17-triones with Human Placental Microsomes
- Biochemical Studies of Estr-4-ene-3,6,17-trione and 5α-Androstan-17-ones with or without a Carbonyl Function at C-3 and/or C-6 as Aromatase Inhibitors
- キャピラリーFTD-GCによる玄米および大豆中15種有機含窒素系農薬の一斉分析法
- アロマターゼ自殺基質Androst-4-ene-3,6,17-trioneの19位酸素化体とN-Acetyl-_L-cysteineとの1,4-付加反応
- Synthesis of Deuterium-Labeled 16α, 19-Dihydroxy C_ Steroids as Internal Standards for Gas Chromatography-Mass Spectrometry
- A Radiometric Assay Method for Aromatase Activity Using [1β-^3H]16α-Hydroxyandrostenedione
- Competitive Inhibition and Suicide Inactivation of Human Placental Aromatase by Androst-4-ene-3,6-dione Derivatives and 3α-Methoxyandrost-4-ene-6,17-dione
- Synthesis of 16α-Hydroxyandrost-4-ene-3,17,19-trione and 3β, 16α-Dihydroxyandrost-5-ene-17,19-dione : Potential Intermediates of Estriol Biosynthesis
- Oxygenation of 2,4-Dibromoestrogens with Nitric Acid : A New Synthesis of 19-Nor Steroids
- Radioimmunoassay of 2-Hydroxyestrone Using Antisera Raised against Antigenic Complexs Obtained by Convenient Methods
- Time-Dependent Inactivation of Human Placental Aromatase by Bromoacetoxy 4-Androsten-3-ones in the Presence of Reduced Nicotinamide Adenine Dinucleotide Phosphate (NADPH)
- Reactions of Enolizable Steroidal 4-En-3-ones and 17-Ones with Hypervalent Iodine
- Stereospecific 1,2-Hydride Shift in the Rearrangement of 16β-Hydroxy-17-oxo Steroids to 17β-Hydroxy-16-ones with Acid and Base(Organic,Chemical)
- Preparation of [1,2-^3H,4-^C]16α-Hydroxyandrostenedione and Its Use for Radiometric Determination of Human Placental Aromatase Activity(Analytical,Chemical)
- Regiospecific Deoxygenation of the Dihydroxyacetone Moiety at C-17 of Corticoid Steroids with Iodotrimethylsilane
- Reaction of 21-Bromo-17α-methoxy-20-ketopregnenes with Sodium Methoxide or Potassium Acetate
- Synthesis of Deuterium-Labelled 16α-Hydroxy-4-androstene-3,17-dione and 16α-Hydroxydehydroepiandrosterone
- Synthesis of Deuterium-labelled Estriol, 16α-Hydroxyestrone and Estriol 16-Glucuronide via 2,4,16α-Tribromoestrone as Internal Standards for Mass Fragmentography
- 急性心筋梗塞のマ-カ-酵素としてのクレアチンキナ-ゼ
- Purification and Characterization of Sialidase from Porcine Liver
- Effects of Inorganic Anions on the Activation of Acid Sialidases
- Effect of Sulfated Compounds on Acid Sialidase
- Identification of 16α, 19-Dihydroxyandrostenedione in the Serum of Pregnant Women by Gas Chromatography-Mass Spectrometry
- DETERMINATION OF AROMATASE ACTIVITY INVOLVED IN THE FORMATION OF ESTRIOL WITH HUMAN PLACENTAL MICROSOMES AND ITS KINETIC PROPERTIES
- Mechanistic Studies of Deoxygenation of Steroidal Ring-D 16,17-Ketols with trimethylsilyl Iodide
- Deoxygenation of Steroidal Ring-D 16,17-Ketols with Trimethylsilyl Iodide