methyl 3-ketocholanate tosylhydrazone | 77285-18-8

• 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: methyl 3-ketocholanate tosylhydrazone
• 英文别名: 3--cholansaeure-methylester；methyl (4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-[(4-methylphenyl)sulfonylhydrazinylidene]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 77285-18-8
• 化学式: C₃₂H₄₈N₂O₄S
• 分子量: 556.81
• InChiKey: BSWSFSRJVKWKKX-XRRWTLKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-ketocholanate tosylhydrazone 在 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 环丁砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以70.4%的产率得到methyl 5β-cholan-24-oate
  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：

  甲基-3-氧代-5beta-胆烷-24-酸酯 、 对甲苯磺酰肼 以 甲醇 、 丙醇 为溶剂， 反应 5.0h， 以5.15 g的产率得到methyl 3-ketocholanate tosylhydrazone
  参考文献：
  名称：

  Quantitative determination of ursodeoxycholic acid and its deuterated derivative in human bile by gas chromatography-mass fragmentography.

  摘要：

  氘标记的熊去氧胆酸（UDCA-d2）是通过氘气对11,12-不饱和胆酸的异相催化还原从胆酸合成的。我们开发了一种通过气相色谱-质谱碎片分析法同时测定人胆汁中的UDCA、UDCA-d2、相关胆酸和胆固醇的新方法。以5β-胆-3-烯-24-酸的甘氨酸结合物为内标，采用自胆酸制备。标定曲线在每种化合物100-500 ng范围内显示出良好的线性关系，并且相对于内标的回收率（95-99%）表明该方法在实际分析人胆汁中的胆酸方面具有足够的准确性。该方法已应用于研究口服给药的UDCA-d2在完全胆漏患者体内的命运。

  DOI：

  10.1248/cpb.29.137

文献信息

• Improved Conditions for Preparation and Reductive Cleavage of Steroidal Ketone Tosylhydrazones
  作者：Takashi Iida、Toshitake Tamura、Taro Matsumoto、Frederic C. Chang

  DOI：10.1055/s-1984-31036

  日期：——
• Caglioti,L. et al., Gazzetta Chimica Italiana, 1964, vol. 94, p. 537 - 551
  作者：Caglioti,L. et al.

  DOI：——

  日期：——