cis-adamantane-2-spiro-3'-8[[(1'H-benzotriazol-1'-yloxy)-carbonyl]methyl]-1',2',4'-trioxaspiro[4.5]decane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: cis-adamantane-2-spiro-3'-8[[(1'H-benzotriazol-1'-yloxy)-carbonyl]methyl]-1',2',4'-trioxaspiro[4.5]decane
• 化学式: C₂₄H₂₉N₃O₅
• 分子量: 439.511
• InChiKey: OLSRFUXGKCXTIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-哌嗪酮 、 cis-adamantane-2-spiro-3'-8[[(1'H-benzotriazol-1'-yloxy)-carbonyl]methyl]-1',2',4'-trioxaspiro[4.5]decane 以 氯仿 为溶剂， 反应 3.0h， 以51%的产率得到cis-adamantane-2-spiro-3'-8'-[[(3'-oxo-1'-piperazinyl)carbonyl]methyl]-1',2',4'-trioxaspiro[4.5]decane
  参考文献：
  名称：

  The Structure−Activity Relationship of the Antimalarial Ozonide Arterolane (OZ277)

  摘要：

  The structure and stereochemistry of the cyclohexane substituents of analogues of arterolane (OZ277) had little effect on potency against in vitro. Weak base functional groups were not required for high antimalarial potency, but they were essential for high antimalarial efficacy in P. berghei-infected mice. Five new ozonides with antimalarial efficacy and ADME profiles superior or equal to that of arterolane were identified.

  DOI：

  10.1021/jm901473s
• 作为产物：
  描述：

  cis-adamantane-2-spiro-3'-8'-carboxymethyl-1',2',4'-trioxaspiro[4.5]decane 、 1-羟基苯并三唑 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以95%的产率得到cis-adamantane-2-spiro-3'-8[[(1'H-benzotriazol-1'-yloxy)-carbonyl]methyl]-1',2',4'-trioxaspiro[4.5]decane
  参考文献：
  名称：

  The Structure−Activity Relationship of the Antimalarial Ozonide Arterolane (OZ277)

  摘要：

  The structure and stereochemistry of the cyclohexane substituents of analogues of arterolane (OZ277) had little effect on potency against in vitro. Weak base functional groups were not required for high antimalarial potency, but they were essential for high antimalarial efficacy in P. berghei-infected mice. Five new ozonides with antimalarial efficacy and ADME profiles superior or equal to that of arterolane were identified.

  DOI：

  10.1021/jm901473s

文献信息

• The Structure−Activity Relationship of the Antimalarial Ozonide Arterolane (OZ277)
  作者：Yuxiang Dong、Sergio Wittlin、Kamaraj Sriraghavan、Jacques Chollet、Susan A. Charman、William N. Charman、Christian Scheurer、Heinrich Urwyler、Josefina Santo Tomas、Christopher Snyder、Darren J. Creek、Julia Morizzi、Maria Koltun、Hugues Matile、Xiaofang Wang、Maniyan Padmanilayam、Yuanqing Tang、Arnulf Dorn、Reto Brun、Jonathan L. Vennerstrom

  DOI：10.1021/jm901473s

  日期：2010.1.14

  The structure and stereochemistry of the cyclohexane substituents of analogues of arterolane (OZ277) had little effect on potency against in vitro. Weak base functional groups were not required for high antimalarial potency, but they were essential for high antimalarial efficacy in P. berghei-infected mice. Five new ozonides with antimalarial efficacy and ADME profiles superior or equal to that of arterolane were identified.