3-[(5-Chloro-2-[[(chloromethyl)oxy]carbonyloxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one | 233676-40-9

• 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-[[(chloromethyl)oxy]carbonyloxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one
• 英文别名: Chloromethyl [4-chloro-2-[[2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]phenyl] carbonate
• CAS: 233676-40-9
• 化学式: C₁₈H₁₁Cl₂F₃N₂O₅
• 分子量: 463.197
• InChiKey: MATXLNAZJDBRBC-UHFFFAOYSA-N

物化性质

• 沸点：
  511.5±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-[(5-Chloro-2-[[(chloromethyl)oxy]carbonyloxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one 在 platinum(IV) oxide 氢气 、 sodium iodide 作用下， 以 乙酸乙酯 、 丙酮 、 苯 为溶剂， 生成 3-[(5-Chloro-2-[[[(phosphonooxy)methyl]oxy]carbonyloxy]-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
• 作为产物：
  描述：

  氯甲酸氯甲酯 、 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 吡啶 作用下， 以 二氯甲烷 为溶剂， 以93.5%的产率得到3-[(5-Chloro-2-[[(chloromethyl)oxy]carbonyloxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one
  参考文献：
  名称：

  Phosphate derivatives of diaryl 1,3,4-oxadiazolone

  摘要：

  本发明提供了具有一般式的新型磷酸盐衍生物，其中A、R^1和R^2如本文所定义，或其无毒的药用可接受盐或溶剂，可用于治疗对钾通道开放有响应的疾病。

  公开号：

  US05939405A1

文献信息

• PHOSPHATE DERIVATIVES OF DIARYL 1,3,4-OXADIAZOLONE
  申请人：Bristol-Myers Squibb Company

  公开号：EP1056754B1

  公开（公告）日：2003-10-22
• Phosphate derivatives of diaryl 1,3,4-oxadiazolone
  申请人：Bristol-Myers Squibb Company

  公开号：US05939405A1

  公开（公告）日：1999-08-17

  The present invention provides novel phosphate derivatives having the general formula wherein A, R.sup.1 and R.sup.2 are as defined herein, or a nontoxic pharmaceutically acceptable salt or solvate thereof and are useful in the treatment of disorders which are responsive to the opening of potassium channels.

  本发明提供了具有一般式的新型磷酸盐衍生物，其中A、R^1和R^2如本文所定义，或其无毒的药用可接受盐或溶剂，可用于治疗对钾通道开放有响应的疾病。
• 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.