6alpha-溴雄甾烯二酮 | 61145-67-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 6alpha-溴雄甾烯二酮
• 英文名称: 6α-bromo-4-androstene-3,17-dione
• 英文别名: 6α-bromoandrost-4-ene-3,17-dione；6α-bromoandrostenedione；6α-bromo-androst-4-ene-3,17-dione；6α-Brom-androst-4-en-3,17-dion；6α-Bromo-4-androsten-3,17-dion；(6alpha)-6-Bromoandrost-4-ene-3,17-dione；(6S,8R,9S,10R,13S,14S)-6-bromo-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 61145-67-3
• 化学式: C₁₉H₂₅BrO₂
• 分子量: 365.31
• InChiKey: HAWQRBIGKRAICT-BMSLSITRSA-N

物化性质

• 熔点：
  171-174°C
• 溶解度：
  可溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6alpha-溴雄甾烯二酮 在 potassium acetate 、 溶剂黄146 作用下， 生成 2α-acetoxyandrost-4-ene-3,17-dione
  参考文献：
  名称：

  Steroids. LX.¹ Synthesis of C-2 Oxygenated Derivatives of Reichstein's Substance S and of Cortisone

  摘要：

  DOI：

  10.1021/ja01606a044
• 作为产物：
  描述：

  雄烯二酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 6alpha-溴雄甾烯二酮
  参考文献：
  名称：

  Aromatase inhibitors. Synthesis and biological activity of androstenedione derivatives

  摘要：

  The synthesis and biological evaluation of androstenedione derivatives as inhibitors of estrogen biosynthesis are described. The results show that 4-hydroxy analogues are among the most potent in vitro inhibitors of the series. Esterification of the 4-hydroxy steroids generally reduced activity. Further conjugation of the 3-keto 4-ene system to give 4-hydroxy-4,6-androstadiene-3,17-dione caused more rapid inactivation of aromatase in rat ovarian microsomes than 4-hydroxyandrostenedione. Some compounds exhibited differences in activity when tested for inhibition of human placental microsomes vs. rat ovarian microsomes. The 4-hydroxyandrostenedione derivatives and their nonbulky esters were generally more potent in vitro and in vivo inhibitors than other substituted steroids in the series. Several of the synthesized compounds markedly reduce (50-81%) estrogen levels in rats on proestrus and/or had antifertility action. To date, none of the compounds surpassed the in vivo inhibitory action of 4-hydroxy-4-androstene-3,17-dione or its 4-acetate derivative.

  DOI：

  10.1021/jm00383a017

文献信息

• 6-Chloro- and 6-Bromo-Substituted Steroids in the Suzuki-Miyaura Cross-Coupling Reaction. A Convenient Route to Potential Aromatase Inhibitors
  作者：Nikolay V. Lukashev、Gennadij V. Latyshev、Pavel A. Donez、George A. Skryabin、Irina P. Beletskaya

  DOI：10.1055/s-2006-926270

  日期：——

  Chlorine at an sp 2 -carbon in steroids has been shown to be reactive in Suzuki-Miyaura cross-coupling reactions with either Ni or Pd catalysts. The coupling of analogous 6-bromo derivatives has also been demonstrated to be applicable to a wider scope of substrates. The Suzuki-Miyaura arylation of 6-bromo-Δ 3 , 5 -steroid enol ethers with subsequent hydrolysis is a useful route to 6-arylated steroids

  类固醇中 sp 2 -碳上的氯已被证明在与 Ni 或 Pd 催化剂的 Suzuki-Miyaura 交叉偶联反应中具有反应性。类似的 6-溴衍生物的偶联也已被证明适用于更广泛的底物。6-溴-Δ 3 , 5-甾体烯醇醚的 Suzuki-Miyaura 芳基化以及随后的水解是获得在饱和碳上带有芳基的 6-芳基化甾体的有用途径。
• COMPOSITION CONTAINING 5$g(a)-DIHYDRO-19-NORETHYSTERONE AND ITS DERIVATIVES CAPABLE OF INHIBITING AROMATASE IN VIVO
  申请人：MEDICAL FOUNDATION OF BUFFALO, INC.

  公开号：EP0417281A1

  公开（公告）日：1991-03-20

  A composition used for inhibiting aromatase in vivo in mammals and containing 5α-dihydro-19-norethysterone (5α-DHNET or its acyl derivative is disclosed. This composition comprises a compound represented by general formula (I) (wherein R, represents hydrogen or C₁₋₂₀ acyl) and a medicinally acceptable carrier or diluent. This composition can be effectively utilized for treatment or prophylaxis ofendocrine dependence of mammals such as mammary cancer, uterine cancer, etc.

  本发明公开了一种用于抑制哺乳动物体内芳香化酶的组合物，其中含有 5α-dihydro-19-norethysterone (5α-DHNET) 或其酰基衍生物。这种组合物由通式 (I) 所代表的化合物（其中 R, 代表氢或 C₁₋₂₀酰基）和医学上可接受的载体或稀释剂组成。该组合物可有效用于治疗或预防哺乳动物的内分泌依赖性疾病，如乳腺癌、子宫癌等。
• Synthesis and some reactions of 6-bromoandrogens: Potential affinity ligand and inactivator of estrogen synthetase
  作者：Mitsuteru Numazawa、Yoshio Osawa

  DOI：10.1016/0039-128x(79)90085-0

  日期：1979.9

  The synthesis of epimeric 6-bromo-4-androstene-3,17-dione (1a and 1b), 6-bromotestosterone (2a and 2b) and its acetate (3a and 3b), and 6-bromo-16 alpha-acetoxy-4-androstene-3,17-dione (5a and 5b), and 6 beta-bromo-16 alpha-hydroxy-4-androstene-3,17-dione (4) is described. The interconversions among compounds 1, 2, and 3 are also studied. The 6 beta-isomer (1b, 2b, and 3b) was epimerized to the 6 alpha-isomer (1a, 2a and 3a) in carbon tetrachloride or chloroform-methanol (9:1) and the 6 alpha-isomer was isolated by fractional crystallization from the epimeric mixture. 6 alpha-Bromo isomer 1a was also epimerized back to 6 beta-bromo isomer 1b in chloroform-methanol (9:1). Two polymorphic forms of 6 beta-bromotestosterone acetate (3b) were isolated (mp. 114--117 degrees and 138--141 degrees). The 6 beta-bromo isomers were found to be unstable in methanol and decomposed to give 5 alpha-androstane-3,6-dione derivative (6). The results of irreversible inactivation of human placental androgen aromatase with some of these 6-bromoandrogens are discussed.
• Steroids. VII.¹ Contribution to the Bromination of ▵⁴-3-Ketosteroids and a New Partial Synthesis of the Natural Estrogens
  作者：Carl Djerassi、G. Rosenkranz、J. Romo、St. Kaufmann、J. Pataki

  DOI：10.1021/ja01166a055

  日期：1950.10
• US4829059A
  申请人：——

  公开号：US4829059A

  公开（公告）日：1989-05-09