methyl(2S)-cyclohexyl{[(3-{[({2,6-dichloro-4-[(trifluoromethyl)oxy]phenyl}amino)carbonyl]amino}-2-naphthalenyl)carbonyl]amino}ethanoate | 887250-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl(2S)-cyclohexyl{[(3-{[({2,6-dichloro-4-[(trifluoromethyl)oxy]phenyl}amino)carbonyl]amino}-2-naphthalenyl)carbonyl]amino}ethanoate
• 英文别名: methyl (2S)-2-cyclohexyl-2-[[3-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]naphthalene-2-carbonyl]amino]acetate
• CAS: 887250-01-3
• 化学式: C₂₈H₂₆Cl₂F₃N₃O₅
• 分子量: 612.433
• InChiKey: VUXOEPZVACBKLN-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl(2S)-cyclohexyl{[(3-{[({2,6-dichloro-4-[(trifluoromethyl)oxy]phenyl}amino)carbonyl]amino}-2-naphthalenyl)carbonyl]amino}ethanoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2S)-cyclohexyl{[(3-{[({2,6-dichloro-4-[(trifluoromethyl)oxy]phenyl}amino)carbonyl]amino}-2-naphthalenyl)carbonyl]amino}ethanoic acid
  参考文献：
  名称：

  Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of type 2 diabetes: 1. Identification of 1-amino-1-cycloalkyl carboxylic acid headgroups

  摘要：

  Optimization of the amino acid residue within a series of anthranilimide-based glycogen phosphorylase inhibitors is described. These studies culminated in the identification of anthranilimides 16 and 22 which displayed potent in vitro inhibition of GPa in addition to reduced inhibition of CYP2C9 and excellent pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.085
• 作为产物：
  描述：

  Methyl(2s)-[(3-amino-2-naphthoyl) amino](cyclohexyl)ethanoate 、 1,3-dichloro-2-isocyanato-5-[(trifluoromethyl)oxy]benzene 在 吡啶 作用下， 生成 methyl(2S)-cyclohexyl{[(3-{[({2,6-dichloro-4-[(trifluoromethyl)oxy]phenyl}amino)carbonyl]amino}-2-naphthalenyl)carbonyl]amino}ethanoate
  参考文献：
  名称：

  Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of type 2 diabetes: 1. Identification of 1-amino-1-cycloalkyl carboxylic acid headgroups

  摘要：

  Optimization of the amino acid residue within a series of anthranilimide-based glycogen phosphorylase inhibitors is described. These studies culminated in the identification of anthranilimides 16 and 22 which displayed potent in vitro inhibition of GPa in addition to reduced inhibition of CYP2C9 and excellent pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.085

文献信息

• Glycogen Phosphorylase Inhibitor Compounds and Pharmaceutical Compositions Thereof
  申请人：Evans Karen

  公开号：US20070249670A1

  公开（公告）日：2007-10-25

  The invention relates to glycogen phosphorylase inhibitor compounds, pharmaceutical compositions of these compounds, methods of treatment using the pharmaceutical compositions to treat diabetes, conditions associated with diabetes, and/or tissue ischemia, including myocardial ischemia, and processes for making the compounds.

  本发明涉及糖原磷酸化酶抑制剂化合物、这些化合物的药物组合物、使用这些药物组合物治疗糖尿病、与糖尿病相关的疾病和/或组织缺血，包括心肌缺血的方法，以及制备这些化合物的过程。