cis-adamantane-2-spiro-3'-8'-(2'-oxo-2'-guanidinoethyl)-1',2',4'-trioxaspiro[4.5]decane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cis-adamantane-2-spiro-3'-8'-(2'-oxo-2'-guanidinoethyl)-1',2',4'-trioxaspiro[4.5]decane
• 化学式: C₁₉H₂₉N₃O₄
• 分子量: 363.457
• InChiKey: DBBAPILKSZYRHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cis-adamantane-2-spiro-3'-8[[(1'H-benzotriazol-1'-yloxy)-carbonyl]methyl]-1',2',4'-trioxaspiro[4.5]decane 、 盐酸胍 在 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 0.33h， 以94%的产率得到cis-adamantane-2-spiro-3'-8'-(2'-oxo-2'-guanidinoethyl)-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.