5'-benzylspiro[adamantane-2,3'-[1,2,4]trioxolane] | 1256776-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧烷
• 英文名称: 5'-benzylspiro[adamantane-2,3'-[1,2,4]trioxolane]
• CAS: 1256776-45-0
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: JYIHSJJMUCVUCO-UHFFFAOYSA-N

物化性质

• 沸点：
  397.7±31.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5'-benzylspiro[adamantane-2,3'-[1,2,4]trioxolane] 在 iron(II) bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 以100%的产率得到苯乙醛
  参考文献：
  名称：

  Endoperoxide Carbonyl Falcipain 2/3 Inhibitor Hybrids: Toward Combination Chemotherapy of Malaria through a Single Chemical Entity

  摘要：

  We extend our approach of combination chemotherapy through a single prodrug entity (O'Neill et al. Angew. Chem., Int. Ed. 2004, 43, 4193) by using a 1,2,4-trioxolane as a protease inhibitor carbonyl-masking group. These molecules are designed to target the malaria parasite through two independent mechanisms of action: iron(II) decomposition releases the carbonyl protease inhibitor and potentially eytotoxic C-radical species in tandem. Using a proposed target "heme", we also demonstrate heme alkylation/carbonyl inhibitor release and quantitatively measure endoperoxide turnover in parasitized red blood cells.

  DOI：

  10.1021/jm1009567
• 作为产物：
  描述：

  苯乙醛 、 adamantan-2-one O-methyloxime 在 臭氧 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 以38%的产率得到5'-benzylspiro[adamantane-2,3'-[1,2,4]trioxolane]
  参考文献：
  名称：

  Endoperoxide Carbonyl Falcipain 2/3 Inhibitor Hybrids: Toward Combination Chemotherapy of Malaria through a Single Chemical Entity

  摘要：

  We extend our approach of combination chemotherapy through a single prodrug entity (O'Neill et al. Angew. Chem., Int. Ed. 2004, 43, 4193) by using a 1,2,4-trioxolane as a protease inhibitor carbonyl-masking group. These molecules are designed to target the malaria parasite through two independent mechanisms of action: iron(II) decomposition releases the carbonyl protease inhibitor and potentially eytotoxic C-radical species in tandem. Using a proposed target "heme", we also demonstrate heme alkylation/carbonyl inhibitor release and quantitatively measure endoperoxide turnover in parasitized red blood cells.

  DOI：

  10.1021/jm1009567