[(3R,5S,8R,9R,10S,13S,14S)-3-(dimethylamino)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15-tetradecahydrocyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate | 1161976-10-8

• 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: [(3R,5S,8R,9R,10S,13S,14S)-3-(dimethylamino)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15-tetradecahydrocyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate
• CAS: 1161976-10-8
• 化学式: C₂₁H₃₂F₃NO₃S
• 分子量: 435.551
• InChiKey: BCMFNYQJFQWSCC-MPXXYZEZSA-N

物化性质

• 沸点：
  470.4±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-tributylstannylisoquinoline 、 [(3R,5S,8R,9R,10S,13S,14S)-3-(dimethylamino)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15-tetradecahydrocyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate 在 四(三苯基膦)钯 、 copper(l) chloride 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 以67%的产率得到(3R,5S,8R,9R,10S,13S,14S)-17-isoquinolin-7-yl-N,N,13-trimethyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15-tetradecahydrocyclopenta[a]phenanthren-3-amine
  参考文献：
  名称：

  Discovery of Potent and Practical Antiangiogenic Agents Inspired by Cortistatin A

  摘要：

  The discovery that cortistatins A and J show noteworthy antiangiogenic activity prompted an investigation of the possibility that simpler and much more easily made compounds based on a steroid core might have useful bioactivity. These studies have led to the development of several potent, water-soluble compounds that may be suitable for local application to treat ocular wet macular degeneration, an important cause of blindness, as well as for treatment of various other angiogenesis-dependent diseases. One of these substances was tested in a mouse retinal angiogenesis model and found to inhibit angiogenesis at a locally administered dose of 500 pmol. Comparison of cell migration data for this and two other synthetic compounds with published data on cortistatin A indicate that they inhibit vascular endothelial growth factor-induced cell migration of human umbilical vein endothelial cells more strongly than cortistatin A.

  DOI：

  10.1021/ja902601e
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 (3R,5S,8R,9R,10S,13S,14S)-3-(dimethylamino)-13-methyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-17-one 在 双(三甲基硅烷基)氨基钾 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 以75%的产率得到[(3R,5S,8R,9R,10S,13S,14S)-3-(dimethylamino)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15-tetradecahydrocyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  [EN] ANGIOGENESIS INHIBITORS
  [FR] INHIBITEURS DE L'ANGIOGENÈSE

  摘要：

  公开号：

  WO2010123545A3

文献信息

• ANGIOGENESIS INHIBITORS
  申请人：Corey Elias James

  公开号：US20120190659A1

  公开（公告）日：2012-07-26

  Compounds of Structural Formula I or pharmaceutically acceptable salts thereof, are effective inhibitors of angiogenesis:

  结构式I的化合物或其药学上可接受的盐，是有效的抑制血管生成的抑制剂：
• [EN] ANGIOGENESIS INHIBITORS<br/>[FR] INHIBITEURS DE L'ANGIOGENÈSE
  申请人：HARVARD COLLEGE

  公开号：WO2010123545A3

  公开（公告）日：2011-02-03
• Discovery of Potent and Practical Antiangiogenic Agents Inspired by Cortistatin A
  作者：Barbara Czakó、László Kürti、Akiko Mammoto、Donald E. Ingber、E. J. Corey

  DOI：10.1021/ja902601e

  日期：2009.7.1

  The discovery that cortistatins A and J show noteworthy antiangiogenic activity prompted an investigation of the possibility that simpler and much more easily made compounds based on a steroid core might have useful bioactivity. These studies have led to the development of several potent, water-soluble compounds that may be suitable for local application to treat ocular wet macular degeneration, an important cause of blindness, as well as for treatment of various other angiogenesis-dependent diseases. One of these substances was tested in a mouse retinal angiogenesis model and found to inhibit angiogenesis at a locally administered dose of 500 pmol. Comparison of cell migration data for this and two other synthetic compounds with published data on cortistatin A indicate that they inhibit vascular endothelial growth factor-induced cell migration of human umbilical vein endothelial cells more strongly than cortistatin A.