3-[[5-Chloro-2-[[[[2-(dimethylamino)ethyl]oxy]carbonyl]oxy]phenyl]methyl]-5-[4(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one | 234433-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[[5-Chloro-2-[[[[2-(dimethylamino)ethyl]oxy]carbonyl]oxy]phenyl]methyl]-5-[4(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one
• 英文别名: [4-Chloro-2-[[2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]phenyl] 2-(dimethylamino)ethyl carbonate
• CAS: 234433-03-5
• 化学式: C₂₁H₁₉ClF₃N₃O₅
• 分子量: 485.847
• InChiKey: ZXVRACRVVBWHBP-UHFFFAOYSA-N

物化性质

• 沸点：
  530.7±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲磺酸甲酯 、 3-[[5-Chloro-2-[[[[2-(dimethylamino)ethyl]oxy]carbonyl]oxy]phenyl]methyl]-5-[4(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one 以 乙酸乙酯 为溶剂， 生成 2-[4-Chloro-2-[[2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]phenoxy]carbonyloxyethyl-trimethylazanium;methanesulfonate
  参考文献：
  名称：

  Synthesis of water-Soluble prodrugs of BMS-191011: A maxi-K channel opener targeted for post-stroke neuroprotection

  摘要：

  A variety of water-soluble prodrugs of BMS-191011 was synthesized and evaluated for solution state stability and rate of conversion to BMS-191011 in rat and human plasma. The deoxycarnitine ester prodrug (11c) was selected for clinical evaluation based on its superior chemical stability, crystallinity and cleavage to BMS-191011 in human plasma. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00296-8
• 作为产物：
  描述：

  3-(5-氯-2-羟基苄基)-5-(4-(三氟甲基)苯基)-1,3,4-噁二唑-2(3h)-酮 在 苄基三苯基氯化膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 3-[[5-Chloro-2-[[[[2-(dimethylamino)ethyl]oxy]carbonyl]oxy]phenyl]methyl]-5-[4(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  Synthesis of water-Soluble prodrugs of BMS-191011: A maxi-K channel opener targeted for post-stroke neuroprotection

  摘要：

  A variety of water-soluble prodrugs of BMS-191011 was synthesized and evaluated for solution state stability and rate of conversion to BMS-191011 in rat and human plasma. The deoxycarnitine ester prodrug (11c) was selected for clinical evaluation based on its superior chemical stability, crystallinity and cleavage to BMS-191011 in human plasma. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00296-8

文献信息

• US6034113A
  申请人：——

  公开号：US6034113A

  公开（公告）日：2000-03-07
• Synthesis of water-Soluble prodrugs of BMS-191011: A maxi-K channel opener targeted for post-stroke neuroprotection
  作者：Piyasena Hewawasam、Min Ding、Nathan Chen、Dalton King、Jay Knipe、Lorraine Pajor、Astrid Ortiz、Valentin K. Gribkoff、John Starrett

  DOI：10.1016/s0960-894x(03)00296-8

  日期：2003.5

  A variety of water-soluble prodrugs of BMS-191011 was synthesized and evaluated for solution state stability and rate of conversion to BMS-191011 in rat and human plasma. The deoxycarnitine ester prodrug (11c) was selected for clinical evaluation based on its superior chemical stability, crystallinity and cleavage to BMS-191011 in human plasma. (C) 2003 Elsevier Science Ltd. All rights reserved.