5-p-toluoyloxy-2-adamantanone | 869671-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-p-toluoyloxy-2-adamantanone
• 英文别名: (4-oxo-1-adamantyl) 4-methylbenzoate
• CAS: 869671-80-7
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: YFOXEYVPDILVIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  5-p-toluoyloxy-2-adamantanone 、 甲氧基胺盐酸盐 在 吡啶 作用下， 以94%的产率得到5-(4-methylbenzoyloxy)-2-adamantanone O-methyl oxime
  参考文献：
  名称：

  Characterization of the two major CYP450 metabolites of ozonide (1,2,4-trioxolane) OZ277

  摘要：

  The antimalarial synthetic ozonide OZ277 (RBx11160) was hydroxylated by human liver microsomes at the distal bridgehead carbon atoms of the spiroadamantane substructure to form two carbinol metabolites devoid of antimalarial activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.087
• 作为产物：
  描述：

  5-羟基-2-金刚烷酮 、 对甲基苯甲酰氯 在 吡啶 作用下， 以90%的产率得到5-p-toluoyloxy-2-adamantanone
  参考文献：
  名称：

  Characterization of the two major CYP450 metabolites of ozonide (1,2,4-trioxolane) OZ277

  摘要：

  The antimalarial synthetic ozonide OZ277 (RBx11160) was hydroxylated by human liver microsomes at the distal bridgehead carbon atoms of the spiroadamantane substructure to form two carbinol metabolites devoid of antimalarial activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.087

文献信息

• Spiro and dispiro 1,2,4-trioxolane antimalarials
  申请人：Vennerstrom L. Jonathan

  公开号：US20050256185A1

  公开（公告）日：2005-11-17

  A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4 -trioxolane is described. The preferred 1,2,4 -trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4 -position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  本发明涉及使用螺环或二螺1,2,4-三氧兰治疗疟疾、血吸虫病和癌症的方法和手段。首选的1,2,4-三氧兰包括一侧为螺烷基团，另一侧为螺环己基团的结构，其中螺环己基团在4位处优选取代。与青蒿素半合成衍生物相比，本发明的化合物结构简单，易于合成，无毒，并且对疟原虫具有很强的杀灭作用。
• SPIRO AND DISPIRO 1,2,4-TRIOXOLANE ANTIMALARIALS
  申请人：VENNERSTROM JONATHAN L.

  公开号：US20080125441A1

  公开（公告）日：2008-05-29

  A means and method for treating malaria, schistosomiasis, and cancer using a Spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  本发明涉及使用Spiro或dispiro 1,2,4-三噁烷治疗疟疾、血吸虫病和癌症的方法和手段。首选的1,2,4-三噁烷包括一个spiroadamantane基团位于三噁烷基团的一侧，而spirocyclohexyl位于三噁烷基团的另一侧，其中spirocyclohexyl环在4位处被取代。与青蒿素半合成衍生物相比，本发明化合物结构简单，易于合成，无毒，并且对疟原虫具有强效作用。
• US7371778B2
  申请人：——

  公开号：US7371778B2

  公开（公告）日：2008-05-13
• [EN] SPIRO AND DISPIRO 1,2,4-TRIOXOLANE ANTIMALARIALS<br/>[FR] ANTIPALUDIQUES SPIRO- ET DISPIRO-1,2,4-TRIOXOLANE
  申请人：MEDICINES MALARIA VENTURE MMV

  公开号：WO2009091433A2

  公开（公告）日：2009-07-23

  A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.