3,17-dioxoandrostane-6-[(E)-ylidene]acetonitrile | 953772-46-8

• 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: 3,17-dioxoandrostane-6-[(E)-ylidene]acetonitrile
• CAS: 953772-46-8
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: YPLOCWQTNWOQKW-PXYGDGKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  57.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,17-dioxoandrostane-6-[(E)-ylidene]acetonitrile 、 2-aminoethoxyamine dihydrochloride 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 (Z)-3-(2-aminoethoxyimino)-17-oxoandrostane-6-[(E)-ylidene]acetonitrile hydrochloride 、 (E)-3-(2-aminoethoxyimino)-17-oxoandrostane-6-[(E)-ylidene]acetonitrile hydrochloride
  参考文献：
  名称：

  Novel analogues of Istaroxime, a potent inhibitor of Na+,K+-ATPase: Synthesis, structure–activity relationship and 3D-quantitative structure–activity relationship of derivatives at position 6 on the androstane scaffold

  摘要：

  We report the synthesis and biological properties of novel analogues of Istaroxime acting as positive inotropic compounds through the inhibition of the Na+, K+-ATPase. We explored the chemical space around the position 6 of the steroidal scaffold by changing the functional groups at that position and maintaining a basic oximic chain in position 3. Some compounds showed inhibitory potencies of the Na+, K+-ATPase higher than Istaroxime and many of the compounds tested in vivo were safer than digoxin, the classic digitalis compound currently used for the treatment of congestive heart failure as inotropic agent. The 3D-QSAR analyses using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to a set of 63 androstane derivatives as Na+,K+-ATPase inhibitors. The contour plots provide many useful insights into relationships between structural features and inhibitory potency. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.095
• 作为产物：
  描述：

  3,3:17,17-bis(ethylendioxy)androstane-6-[(E)-ylidene]acetonitrile 在 对甲苯磺酸一水合物 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以87%的产率得到3,17-dioxoandrostane-6-[(E)-ylidene]acetonitrile
  参考文献：
  名称：

  Novel analogues of Istaroxime, a potent inhibitor of Na+,K+-ATPase: Synthesis, structure–activity relationship and 3D-quantitative structure–activity relationship of derivatives at position 6 on the androstane scaffold

  摘要：

  We report the synthesis and biological properties of novel analogues of Istaroxime acting as positive inotropic compounds through the inhibition of the Na+, K+-ATPase. We explored the chemical space around the position 6 of the steroidal scaffold by changing the functional groups at that position and maintaining a basic oximic chain in position 3. Some compounds showed inhibitory potencies of the Na+, K+-ATPase higher than Istaroxime and many of the compounds tested in vivo were safer than digoxin, the classic digitalis compound currently used for the treatment of congestive heart failure as inotropic agent. The 3D-QSAR analyses using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to a set of 63 androstane derivatives as Na+,K+-ATPase inhibitors. The contour plots provide many useful insights into relationships between structural features and inhibitory potency. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.095