3α-acetyl-23,24-dinor-5β-cholan-22-al | 19707-22-3

• 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: 3α-acetyl-23,24-dinor-5β-cholan-22-al
• 英文别名: 3-acetoxy-23,24-dinor-5β-cholan-22-al；[(3R,5R,8R,9S,10S,13S,14S,17R)-10,13-dimethyl-17-[(2S)-1-oxopropan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 19707-22-3
• 化学式: C₂₄H₃₈O₃
• 分子量: 374.564
• InChiKey: GGPDZUNHOAQEIZ-CVJBFQIQSA-N

物化性质

• 熔点：
  119-120 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  456.7±18.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-acetyl-23,24-dinor-5β-cholan-22-al 在 氧气 、 rose bengal 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以78%的产率得到孕烷醇酮
  参考文献：
  名称：

  Bile Acid-Based 1,2,4-Trioxanes: Synthesis and Antimalarial Assessment

  摘要：

  A new series of bile acid-based trioxanes 23a-d, 24a-d, 25a-d, 26a, 26b, and 26d have been synthesized and assessed for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. The antimalarial activity of these trioxanes showed a strong dependence on the side-chain length; shortening side-chain length lead to increase in activity. The antimalarial activity also showed even stronger dependence on the stereochemistry at C3 and C6 (C21 in Figure 5) of the trioxane moiety. Of the two diastereomers isolated of each of the trioxanes, more polar one was significantly more active than the less polar one. The more polar diastereomer of the trioxanes 26a, 26b, and 26d, were the most active compounds of the series. All these three trioxanes provided 100% protection at 24 mg/kg X 4 days. In this model beta-arteether provided 100% and 20% protection at 48 mg/kg X 4 days and 24 mg/kg X 4 days, respectively.

  DOI：

  10.1021/jm301323k
• 作为产物：
  描述：

  石胆酸 在 吡啶 、 4-二甲氨基吡啶 、 periodic acid dihydrate 、 copper diacetate 、 lead(IV) tetraacetate 、 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 27.0h， 生成 3α-acetyl-23,24-dinor-5β-cholan-22-al
  参考文献：
  名称：

  Bile Acid-Based 1,2,4-Trioxanes: Synthesis and Antimalarial Assessment

  摘要：

  A new series of bile acid-based trioxanes 23a-d, 24a-d, 25a-d, 26a, 26b, and 26d have been synthesized and assessed for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. The antimalarial activity of these trioxanes showed a strong dependence on the side-chain length; shortening side-chain length lead to increase in activity. The antimalarial activity also showed even stronger dependence on the stereochemistry at C3 and C6 (C21 in Figure 5) of the trioxane moiety. Of the two diastereomers isolated of each of the trioxanes, more polar one was significantly more active than the less polar one. The more polar diastereomer of the trioxanes 26a, 26b, and 26d, were the most active compounds of the series. All these three trioxanes provided 100% protection at 24 mg/kg X 4 days. In this model beta-arteether provided 100% and 20% protection at 48 mg/kg X 4 days and 24 mg/kg X 4 days, respectively.

  DOI：

  10.1021/jm301323k

文献信息

• Johnson et al., Journal of the Chemical Society, 1954, p. 1302,1305
  作者：Johnson et al.

  DOI：——

  日期：——
• Daglish et al., Journal of the Chemical Society, 1954, p. 2627,2630
  作者：Daglish et al.

  DOI：——

  日期：——
• Doery et al., Acta Chimica Academiae Scientiarum Hungaricae, 1959, vol. 20, p. 67,71
  作者：Doery et al.

  DOI：——

  日期：——
• J. Med. Chem. 2012, 55, 10662-10673
  作者：

  DOI：——

  日期：——