3β-cyano-5α-cholestane | 1251-66-7

• 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: 3β-cyano-5α-cholestane
• 英文别名: 3β-cyanocholestane；5α-cholestane-3β-carbonitrile；5α-Cholestan-3β-carbonitril；3β-Cyano-5α-cholestan；(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3-carbonitrile
• CAS: 1251-66-7
• 化学式: C₂₈H₄₇N
• 分子量: 397.688
• InChiKey: VTVYVUMMFBADCT-PGAJIAHISA-N

物化性质

• 熔点：
  151-152 °C(Solv: acetone (67-64-1))
• 沸点：
  493.8±14.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-cyano-5α-cholestane 在 sodium hydroxide 、 乙二醇甲醚 作用下， 生成 5α-cholestane-3β-carboxylic acid
  参考文献：
  名称：

  Labler et al., Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 1249,1254

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 1,4-二氧六环 、 Lindlar's catalyst 作用下， 生成 3β-cyano-5α-cholestane
  参考文献：
  名称：

  Labler et al., Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 1249,1254

  摘要：

  DOI：

文献信息

• Roberts et al., Journal of the Chemical Society, 1954, p. 2705,2712
  作者：Roberts et al.

  DOI：——

  日期：——
• Evaluation of steroidal amines as lipid raft modulators and potential anti-influenza agents
  作者：Sameer Agarwal、Cornelia Schroeder、Georg Schlechtingen、Tobias Braxmeier、Gary Jennings、Hans-Joachim Knölker

  DOI：10.1016/j.bmcl.2013.07.015

  日期：2013.9

  The influenza A virus (IFV) possesses a highly ordered cholesterol-rich lipid envelope. A specific composition and structure of this membrane raft envelope are essential for viral entry into cells and virus budding. Several steroidal amines were investigated for antiviral activity against IFV. Both, a positively charged amino function and the highly hydrophobic (ClogP >= 5.9) ring system are required for IC50 values in the low mu M range. An amino substituent is preferential to an azacyclic A-ring. We showed that these compounds either disrupt or augment membrane rafts and in some cases inactivate the free virus. Some of the compounds also interfere with virus budding. The antiviral selectivity improved in the series 3-amino, 3-aminomethyl, 3-aminoethyl, or by introducing an OH function in the A-ring. Steroidal amines show a new mode of antiviral action in directly targeting the virus envelope and its biological functions. (C) 2013 Elsevier Ltd. All rights reserved.
• Roberts et al., Journal of the Chemical Society, <1954> 2705, 2714
  作者：Roberts et al.

  DOI：——

  日期：——