5α-3-methylene>cholestane

• 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: 5α-3-methylene>cholestane
• 英文别名: 5α-3-[bis[5'-chloro-4'-methoxy-3'-(methoxycarbonyl)phenyl]methylene]cholestane；methyl 3-chloro-5-[(3-chloro-4-methoxy-5-methoxycarbonylphenyl)-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]methyl]-2-methoxybenzoate
• 化学式: C₄₆H₆₂Cl₂O₆
• 分子量: 781.901
• InChiKey: BLCLHGOFFAWXQO-OIQZAZJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5α-3-methylene>cholestane 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以0.159 g的产率得到5α-3-methylene>cholestane
  参考文献：
  名称：

  Cosalane Analogs with Enhanced Potencies as Inhibitors of HIV-1 Protease and Integrase

  摘要：

  Several new analogues of the novel anti-HIV agent cosalane have been synthesized and evaluated as inhibitors of HIV-1 integrase and protease, HIV-1 replication, HIV-1 and HIV-2 cytopathicity, HIV-1- and HIV-2-mediated syncytium formation, and cytopathicity of a variety of human pathogenic viruses. The congeners displayed enhanced potencies relative to cosalane itself as inhibitors of HIV-1 integrase and protease. The two most potent analogues against HIV-1 integrase displayed IC50 values of 2.2 mu M, while the three most potent compounds against HIV-1 protease had IC50 values in the 0.35-0.39 mu M range. In addition to its activity against HIV-1 and HIV-2 cytopathicity, cosalane inhibited the cytopathic effects of herpes simplex virus-1, herpes simplex virus-2, and human cytomegalovirus at concentrations that were well below the cytotoxic concentrations. Potentially useful antiviral activities were also revealed for some of the new cosalane congeners against influenza virus, Junin virus, and Tacaribe virus.

  DOI：

  10.1021/jm00003a007
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 、 3,3'-dichloro-4,4'-dimethoxy-5,5'-bis(methoxycarbonyl)benzophenone 在 titanium(III) chloride 、 铜 、 锌 作用下， 生成 5α-3-methylene>cholestane
  参考文献：
  名称：

  Cosalane Analogs with Enhanced Potencies as Inhibitors of HIV-1 Protease and Integrase

  摘要：

  Several new analogues of the novel anti-HIV agent cosalane have been synthesized and evaluated as inhibitors of HIV-1 integrase and protease, HIV-1 replication, HIV-1 and HIV-2 cytopathicity, HIV-1- and HIV-2-mediated syncytium formation, and cytopathicity of a variety of human pathogenic viruses. The congeners displayed enhanced potencies relative to cosalane itself as inhibitors of HIV-1 integrase and protease. The two most potent analogues against HIV-1 integrase displayed IC50 values of 2.2 mu M, while the three most potent compounds against HIV-1 protease had IC50 values in the 0.35-0.39 mu M range. In addition to its activity against HIV-1 and HIV-2 cytopathicity, cosalane inhibited the cytopathic effects of herpes simplex virus-1, herpes simplex virus-2, and human cytomegalovirus at concentrations that were well below the cytotoxic concentrations. Potentially useful antiviral activities were also revealed for some of the new cosalane congeners against influenza virus, Junin virus, and Tacaribe virus.

  DOI：

  10.1021/jm00003a007