methyl (4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-6'-[1-(4-bromophenyl)ethenyl]-10,13-dimethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,3'-1,2,4-trioxane]-17-yl]pentanoate | 1415548-82-1

• 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 (4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-6'-[1-(4-bromophenyl)ethenyl]-10,13-dimethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,3'-1,2,4-trioxane]-17-yl]pentanoate
• CAS: 1415548-82-1
• 化学式: C₃₅H₄₉BrO₅
• 分子量: 629.675
• InChiKey: HEFGNWUMTNSDDF-NFUYZVGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  石胆酸 在 盐酸 、 Jones reagent 、 对甲苯磺酸 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 10.25h， 生成 methyl (4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-6'-[1-(4-bromophenyl)ethenyl]-10,13-dimethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,3'-1,2,4-trioxane]-17-yl]pentanoate
  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

• Bile Acid-Based 1,2,4-Trioxanes: Synthesis and Antimalarial Assessment
  作者：Chandan Singh、Mohammad Hassam、Ved Prakash Verma、Ajit Shanker Singh、Niraj Krishna Naikade、Sunil K. Puri、Prakas R. Maulik、Ruchir Kant

  DOI：10.1021/jm301323k

  日期：2012.12.13

  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.