16-(benzo[1,3]dioxol-5-ylmethylene)androsta-1,4-diene-3,17-dione | 1414852-35-9

• 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: 16-(benzo[1,3]dioxol-5-ylmethylene)androsta-1,4-diene-3,17-dione
• 英文别名: (16E)-16-(1,3-Benzodioxol-5-ylmethylene)androsta-1,4-diene-3,17-dione；(8R,9S,10R,13S,14S,16E)-16-(1,3-benzodioxol-5-ylmethylidene)-10,13-dimethyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS: 1414852-35-9
• 化学式: C₂₇H₂₈O₄
• 分子量: 416.517
• InChiKey: CICFJJFSPNICFO-ATVBXKRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胡椒醛 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 甲醇 、 环己酮 、 甲苯 、 苯 为溶剂， 反应 52.0h， 生成 16-(benzo[1,3]dioxol-5-ylmethylene)androsta-1,4-diene-3,17-dione
  参考文献：
  名称：

  Synthesis and aromatase inhibitory activity of some new 16E-arylidenosteroids

  摘要：

  A new series of 16E-arylidene androstene derivatives has been synthesized and evaluated for aromatase inhibitory activity. The impact of various aryl substituents at 16 position of the steroid skeleton on aromatase inhibitory activity has been observed. The 16E-arylidenosteroids 6, 10 and 11 exhibited significant inhibition of the aromatase enzyme. 16-(4-Pyridylmethylene)-4-androstene-3,17-dione (6, IC50: 5.2 mu M) and 16-(benzo-[1,3]dioxol-5-ylmethylene)androsta-1,4-diene-3,17-dione (11, IC50: 6.4 mu M) were found to be approximately five times more potent in comparison to aminoglutethimide. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2012.08.005

文献信息

• Synthesis and aromatase inhibitory activity of some new 16E-arylidenosteroids
  作者：Ranju Bansal、Sridhar Thota、Nalin Karkra、Maninder Minu、Christina Zimmer、Rolf W. Hartmann

  DOI：10.1016/j.bioorg.2012.08.005

  日期：2012.12

  A new series of 16E-arylidene androstene derivatives has been synthesized and evaluated for aromatase inhibitory activity. The impact of various aryl substituents at 16 position of the steroid skeleton on aromatase inhibitory activity has been observed. The 16E-arylidenosteroids 6, 10 and 11 exhibited significant inhibition of the aromatase enzyme. 16-(4-Pyridylmethylene)-4-androstene-3,17-dione (6, IC50: 5.2 mu M) and 16-(benzo-[1,3]dioxol-5-ylmethylene)androsta-1,4-diene-3,17-dione (11, IC50: 6.4 mu M) were found to be approximately five times more potent in comparison to aminoglutethimide. (C) 2012 Elsevier Inc. All rights reserved.