4-(p-methoxyphenyl)androst-4-ene-3,17-dione

• 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
• 英文名称: 4-(p-methoxyphenyl)androst-4-ene-3,17-dione
• 英文别名: (8R,9S,10R,13S,14S)-4-(4-methoxyphenyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• 化学式: C₂₆H₃₂O₃
• 分子量: 392.538
• InChiKey: WOYGAVVZKLVPDO-NRUSOEPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(p-methoxyphenyl)androst-4-ene-3,17-dione 在 氢溴酸 、 溶剂黄146 作用下， 反应 2.0h， 以48%的产率得到4-(p-hydroxyphenyl)androst-4-ene-3,17-dione
  参考文献：
  名称：

  4- and 6-(p-Sulphamoylphenyl)androstenediones: Studies of aromatase inhibitor-based oestrone sulphatase inhibition

  摘要：

  4-(p-Sulphamoylphenyl)androstenedione (3) and 6 alpha-p-sulphamoylphenyl analogues 12-14 were synthesised and tested as aromatase inhibitors as well as oestrone sulphatase inhibitors in human placental microsomes. All of the p-sulphamoylphenyl compounds synthesised were powerful inhibitors of aromatase with apparent K-i values ranging between 30 and 97 nM. In addition, the aromatase inhibitory activities of 6 alpha-p-hydroxyphenyl compounds 9-11, which may be produced from their respective sulphamoylphenyl compounds by action of oestrone sulphatase, were also high in a range of 23 and 75 nM of the K-i values. On the other hand, all of the sulphamoylphenyl compounds were poor inhibitors of oestrone sulphatase with more than about 200 mu M of IC25 values. Although the present findings of the oestrone sulphatase inhibition are disappointing, such attempts may be valuable to develop a new class of drugs having a dual function, aromatase inhibitor and oestrone sulphatase inhibitor, for the treatment of oestrogen-dependent breast cancer. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.05.011
• 作为产物：
  描述：

  雄烯二酮 在 bis-triphenylphosphine-palladium(II) chloride 环氧乙烷 、 溴 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 4-(p-methoxyphenyl)androst-4-ene-3,17-dione
  参考文献：
  名称：

  通过 Suzuki-Miyaura 交叉偶联反应轻松合成 4-和 6-芳基取代的类固醇

  摘要：

  潜在的芳香酶抑制剂 -4- 和 6-芳基取代的雄激素-4-ene-3,17-二酮和 17-羟基孕酮衍生物 - 已通过 Suzuki-Miyaura 交叉偶联从其相应的 4-和 6-溴类固醇制备.

  DOI：

  10.1055/s-2005-865287

文献信息

• Lukashev, Nikolay V.; Averin, Alexei D.; Latyshev, Gennadij V., Polish Journal of Chemistry, 2006, vol. 80, # 4, p. 559 - 572
  作者：Lukashev, Nikolay V.、Averin, Alexei D.、Latyshev, Gennadij V.、Donez, Pavel A.、Ranyuk, Elena R.、Beletskaya, Irina P.

  DOI：——

  日期：——
• A Facile Synthesis of 4- and 6-Aryl-Substituted Steroids by the Suzuki-Miyaura­ Cross-Coupling Reaction
  作者：Nikolai V. Lukashev、Gennadij V. Latyshev、Pavel A. Donez、George A. Skryabin、Irina P. Beletskaya

  DOI：10.1055/s-2005-865287

  日期：——

  Potential aromatase inhibitors -4- and 6-aryl-substituted derivatives of androst-4-ene-3,17-dione and 17-hydroxyprogesterone - have been prepared by the Suzuki-Miyaura cross-coupling from their corresponding 4- and 6-bromosteroids.

  潜在的芳香酶抑制剂 -4- 和 6-芳基取代的雄激素-4-ene-3,17-二酮和 17-羟基孕酮衍生物 - 已通过 Suzuki-Miyaura 交叉偶联从其相应的 4-和 6-溴类固醇制备.
• 4- and 6-(p-Sulphamoylphenyl)androstenediones: Studies of aromatase inhibitor-based oestrone sulphatase inhibition
  作者：Yoko Watari、Satoshi Yamaguchi、Madoka Takahashi、Masao Nagaoka、Mitsuteru Numazawa

  DOI：10.1016/j.steroids.2010.05.011

  日期：2010.12

  4-(p-Sulphamoylphenyl)androstenedione (3) and 6 alpha-p-sulphamoylphenyl analogues 12-14 were synthesised and tested as aromatase inhibitors as well as oestrone sulphatase inhibitors in human placental microsomes. All of the p-sulphamoylphenyl compounds synthesised were powerful inhibitors of aromatase with apparent K-i values ranging between 30 and 97 nM. In addition, the aromatase inhibitory activities of 6 alpha-p-hydroxyphenyl compounds 9-11, which may be produced from their respective sulphamoylphenyl compounds by action of oestrone sulphatase, were also high in a range of 23 and 75 nM of the K-i values. On the other hand, all of the sulphamoylphenyl compounds were poor inhibitors of oestrone sulphatase with more than about 200 mu M of IC25 values. Although the present findings of the oestrone sulphatase inhibition are disappointing, such attempts may be valuable to develop a new class of drugs having a dual function, aromatase inhibitor and oestrone sulphatase inhibitor, for the treatment of oestrogen-dependent breast cancer. (C) 2010 Elsevier Inc. All rights reserved.