4-chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl-4-(dimethylamino)butyrate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl-4-(dimethylamino)butyrate
• 英文别名: [4-Chloro-2-[[2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]phenyl] 4-(dimethylamino)butanoate
• 化学式: C₂₂H₂₁ClF₃N₃O₄
• 分子量: 483.875
• InChiKey: BWFHHONZPVJIHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲磺酸甲酯 、 4-chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl-4-(dimethylamino)butyrate 以 乙酸乙酯 为溶剂， 生成 [4-[4-Chloro-2-[[2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]phenoxy]-4-oxobutyl]-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：

  4-(dimethylamino)butanoyl chloride hydrochloride 、 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 sodium hydride 作用下， 以 乙醚 为溶剂， 生成 4-chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl-4-(dimethylamino)butyrate
  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

• [EN] DERIVATIVES OF 1,3,4-OXADIAZOLONE<br/>[FR] DERIVES BENZOATE DE 1,3,4-OXADIAZOLONE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999038510A1

  公开（公告）日：1999-08-05

  (EN) The present invention provides novel oxadiazolone derivatives having general formula (I), wherein A, B, D and R 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 the large conductance calcium-activated potassium channels.(FR) Cette invention, qui a trait à de nouveaux dérivés benzoate correspondant à la formule générale: dans laquelle A, B, D et R sont tels que définis dans le descriptif, concerne également un sel ou un solvate, non toxique et acceptable du point de vue pharmaceutique, de ces dérivés. Ces substances sont efficaces dans le cadre du traitement d'affections influencées par l'ouverture des canaux potassium à importante conductance activés par le calcium.

  (EN) 本发明提供了具有一般式（I）的新型噁唑酮衍生物，其中A、B、D和R如本文所定义，或其无毒药学上可接受的盐或溶剂，在治疗对大电导钙激活钾通道开放有反应的疾病方面具有用处。 (FR) 本发明提供了新的苯甲酸酯衍生物，其通式如下：其中A、B、D和R如本文所定义，或其无毒药学上可接受的盐或溶剂，可用于治疗对开放大电导钙激活钾通道有反应的疾病。
• EP1051173A4
  申请人：——

  公开号：EP1051173A4

  公开（公告）日：2002-07-31
• DERIVATIVES OF 1,3,4-OXADIAZOLONE
  申请人：Bristol-Myers Squibb Company

  公开号：EP1051173A1

  公开（公告）日：2000-11-15
• 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.