6-溴雄酮 | 38632-00-7

• 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: 6-溴雄酮
• 中文别名: 6-溴雄烯二酮；6-溴雄烯酮
• 英文名称: 6β-bromoandrost-4-ene-3,17-dione
• 英文别名: 6β-bromo-4-androstene-3,17-dione；6-Bromoandrostenedione；(6R,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: 38632-00-7
• 化学式: C₁₉H₂₅BrO₂
• 分子量: 365.31
• InChiKey: HAWQRBIGKRAICT-DQXCSHPPSA-N

物化性质

• 熔点：
  158-163°C (dec.)
• 沸点：
  467.0±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、甲醇（非常轻微。加热。超声处理）

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

安全信息

• 储存条件：
  室温下，请密封保存。

制备方法与用途

制备方法： 这是一种医药中间体。

用途简介：目前暂无具体用途说明。

反应信息

• 作为反应物：
  描述：

  6-溴雄酮 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以58%的产率得到4,6-雄烯二醇-3,17-二酮
  参考文献：
  名称：

  Mann, John; Pietrzak, Barbara, Journal of the Chemical Society. Perkin transactions I, 1983, # 11, p. 2681 - 2685

  摘要：

  DOI：
• 作为产物：
  描述：

  雄烯二酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 6-溴雄酮
  参考文献：
  名称：

  Synthesis and some reactions of 6-bromoandrogens: Potential affinity ligand and inactivator of estrogen synthetase

  摘要：

  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.

  DOI：

  10.1016/0039-128x(79)90085-0

文献信息

• Benign Synthesis of Thiazolo-androstenone Derivatives as Potent Anticancer Agents
  作者：Mohamad Akbar Ali、ChrisTina Okolo、Zakeyah A. Alsharif、Jedidiah Whitt、Steven A. Chambers、Rajender S. Varma、Mohammad A. Alam

  DOI：10.1021/acs.orglett.8b02587

  日期：2018.9.21

  been rationalized by density functional theory calculations. This benign methodology accentuates a domino protocol deploying a renewable solvent, ethanol, while generating novel compounds that display potent growth inhibitory effects in in vitro studies for several cancer cell lines at submicromolar concentrations.

  已发现硫脲衍生物与6β-溴代雄烯二酮的空前反应可通过一种简单，安全，级联的方法形成氨基噻唑基-雄烯二酮，该协议能够通过使用现成的试剂合成新分子。通过密度泛函理论计算已经合理化了产物形成的反应机理。这种良性方法强调了使用可再生溶剂乙醇的多米诺协议，同时生成了在亚微摩尔浓度的几种癌细胞体外研究中显示出有效生长抑制作用的新型化合物。
• 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。
• Aromatase inhibitors. Synthesis and biological activity of androstenedione derivatives
  作者：David A. Marsh、Harry J. Brodie、Wesley Garrett、Chon Hwa Tsai-Morris、Angela M. H. Brodie

  DOI：10.1021/jm00383a017

  日期：1985.6

  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.
• Drew, Michael G. B.; Mann, John; Pietrzak, Barbara, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1049 - 1054
  作者：Drew, Michael G. B.、Mann, John、Pietrzak, Barbara

  DOI：——

  日期：——