TU-501 | 104685-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: TU-501
• 英文别名: 2-[(4-Methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1,4-dihydroimidazo[4,5-b]pyridin-5-one
• CAS: 104685-51-0
• 化学式: C₁₅H₁₆N₄O₂S
• 分子量: 316.384
• InChiKey: CUGAMTHJIBXNQB-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179.5 °C(Solv: ethanol (64-17-5))
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  TU-501 在 titanium(IV) isopropylate 、 过氧化氢异丙苯 、 (1R,2S)-1-氨基-2-茚醇 作用下， 以 异丙苯 、 1-methyl-2-pyrrolidine (NMP) 为溶剂， 反应 16.0h， 以90%的产率得到(S)-tenatoprazole
  参考文献：
  名称：

  A new titanate/(+)-(1R,2S)-cis-1-amino-2-indanol system for the asymmetric synthesis of (S)-tenatoprazole

  摘要：

  Tenatoprazole, a substituted imidazopyridinyl derivative, is an irreversible proton pump inhibitor (PPI), which is used for the prevention and treatment of gastric acid-related diseases. A new highly efficient asymmetric oxidation using cumene hydroperoxide (CHP) as the oxidant in the presence of titanium tetraisopropoxide (Ti(OiPr)(4)) and (+)-(1R,2S)-cis-1-amino-2-indanol, in a polar aprotic solvent at 0-20 degrees C, has been developed to prepare tenatoprazole with an enantiomeric excess of >99%, a chemoselectivity of >90% and a chemical yield of >90% from the corresponding sulfide. This procedure was successfully implemented on scales ranging from 100 mg to multiple kilograms. Detailed studies of the parameters controlling purity and yield for this reaction are presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.111

文献信息

• Skin Lightening Compositions
  申请人：ELC Management LLC

  公开号：US20150086497A1

  公开（公告）日：2015-03-26

  Compositions and methods for lightening and/or depigmenting skin are provided, the compositions comprising compounds having the structure: or having the structure: as defined herein.
• SKIN LIGHTENING COMPOSITIONS
  申请人：ELC Management LLC

  公开号：US20170035672A1

  公开（公告）日：2017-02-09

  Compositions and methods for lightening and/or depigmenting skin are provided, the compositions comprising compounds having the structure: or having the structure: as defined herein.
• US8722026B2
  申请人：——

  公开号：US8722026B2

  公开（公告）日：2014-05-13
• US9314415B2
  申请人：——

  公开号：US9314415B2

  公开（公告）日：2016-04-19