4-phenoxy-4,6-androstadiene-3,17-dione | 167639-83-0

• 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-phenoxy-4,6-androstadiene-3,17-dione
• 英文别名: (8R,9S,10R,13S,14S)-10,13-dimethyl-4-phenoxy-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 167639-83-0
• 化学式: C₂₅H₂₈O₃
• 分子量: 376.496
• InChiKey: CHSLBFAEQJZJHY-BKCLIDBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  苯硫酚 、 4-phenoxy-4,6-androstadiene-3,17-dione 在 sodium 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以210 mg的产率得到4-phenoxy-7α-(phenylthio)-4-androstene-3,17-dione
  参考文献：
  名称：

  Probing the Hydrophobic Pocket of the Active Site of Aromatase with 4-Phenoxy-7.alpha.-(phenylthio)-4-androstene-3,17-dione

  摘要：

  In order to examine the nature of the hydrophobic pocket at the active site of aromatase, we carried out the synthesis, biochemical evaluation, and molecular modeling studies on 4-phenoxy-7 alpha-(phenylthio)-4-androstene dione 2. Aromatase inhibitory activity of 2 was found to be significantly weaker than that of the 4- and 7 alpha-mono(phenylthio)-substituted derivatives of androstenedione. These results along with those obtained from the modeling studies suggest the existence of a single hydrophobic pocket corresponding to the a-face in the C4, C6, C7 region of androstenedione.

  DOI：

  10.1021/jm00020a031
• 作为产物：
  描述：

  福美司坦 在 吡啶 、 水 、 methylcopper 、 对甲苯磺酸 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 26.05h， 生成 4-phenoxy-4,6-androstadiene-3,17-dione
  参考文献：
  名称：

  Probing the Hydrophobic Pocket of the Active Site of Aromatase with 4-Phenoxy-7.alpha.-(phenylthio)-4-androstene-3,17-dione

  摘要：

  In order to examine the nature of the hydrophobic pocket at the active site of aromatase, we carried out the synthesis, biochemical evaluation, and molecular modeling studies on 4-phenoxy-7 alpha-(phenylthio)-4-androstene dione 2. Aromatase inhibitory activity of 2 was found to be significantly weaker than that of the 4- and 7 alpha-mono(phenylthio)-substituted derivatives of androstenedione. These results along with those obtained from the modeling studies suggest the existence of a single hydrophobic pocket corresponding to the a-face in the C4, C6, C7 region of androstenedione.

  DOI：

  10.1021/jm00020a031

文献信息

• Probing the Hydrophobic Pocket of the Active Site of Aromatase with 4-Phenoxy-7.alpha.-(phenylthio)-4-androstene-3,17-dione
  作者：Xing-Ping Liu、Didier M. Lambert、Yusuf J. Abul-Hajj

  DOI：10.1021/jm00020a031

  日期：1995.9

  In order to examine the nature of the hydrophobic pocket at the active site of aromatase, we carried out the synthesis, biochemical evaluation, and molecular modeling studies on 4-phenoxy-7 alpha-(phenylthio)-4-androstene dione 2. Aromatase inhibitory activity of 2 was found to be significantly weaker than that of the 4- and 7 alpha-mono(phenylthio)-substituted derivatives of androstenedione. These results along with those obtained from the modeling studies suggest the existence of a single hydrophobic pocket corresponding to the a-face in the C4, C6, C7 region of androstenedione.