7-α-dicyanomethylcholesteryl 3β-acetate | 916763-73-0

• 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: 7-α-dicyanomethylcholesteryl 3β-acetate
• 英文别名: [(3S,7S,8S,9S,10R,13R,14S,17R)-7-(dicyanomethyl)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 916763-73-0
• 化学式: C₃₂H₄₈N₂O₂
• 分子量: 492.745
• InChiKey: JKPNUZPHXJFKCY-PEZKWIRASA-N

物化性质

• 沸点：
  594.1±30.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-α-dicyanomethylcholesteryl 3β-acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以50%的产率得到7-α-dicyanomethylcholesterol
  参考文献：
  名称：

  Synthesis of oxysterols and nitrogenous sterols with antileishmanial and trypanocidal activities

  摘要：

  Two sterol families have been synthesized: the first one is nitrogenous sterols containing amino, N-hydroxyimino or cyano group and the second one is oxysterols such as ketosterol and hydroxysterols. These compounds were then evaluated in vitro against Leishmania donovani promastigotes and Thypanosoma brucei brucei trypomastigotes. The most active compounds against L. donovani promastigotes were 7 beta-aminomethylcholesterol and 7 alpha,beta-aminocholesterol (IC50 in a range from 1 to 3 mu M, pentamidine: 2.8 mu M). These compounds were active on intramacrophage amastigotes with IC50 of 1.3 mu M. Such an activity justifies further in vivo antileishmanial evaluation. Against T. b. brucei, (24R, S)-24-hydroxy-24-methyl cholesterol (MEC, 12.5 mu M) was the most active compound from these series. (c) 2006 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2006.03.033
• 作为产物：
  描述：

  胆固醇醋酸酯 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 48.0h， 生成 7-α-dicyanomethylcholesteryl 3β-acetate
  参考文献：
  名称：

  Synthesis of oxysterols and nitrogenous sterols with antileishmanial and trypanocidal activities

  摘要：

  Two sterol families have been synthesized: the first one is nitrogenous sterols containing amino, N-hydroxyimino or cyano group and the second one is oxysterols such as ketosterol and hydroxysterols. These compounds were then evaluated in vitro against Leishmania donovani promastigotes and Thypanosoma brucei brucei trypomastigotes. The most active compounds against L. donovani promastigotes were 7 beta-aminomethylcholesterol and 7 alpha,beta-aminocholesterol (IC50 in a range from 1 to 3 mu M, pentamidine: 2.8 mu M). These compounds were active on intramacrophage amastigotes with IC50 of 1.3 mu M. Such an activity justifies further in vivo antileishmanial evaluation. Against T. b. brucei, (24R, S)-24-hydroxy-24-methyl cholesterol (MEC, 12.5 mu M) was the most active compound from these series. (c) 2006 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2006.03.033