Methyl N-[(3-amino-2-naphthalenyl)carbonyl]-O-(phenylmethyl)-L-threoninate | 887246-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl N-[(3-amino-2-naphthalenyl)carbonyl]-O-(phenylmethyl)-L-threoninate
• 英文别名: methyl (2S,3R)-2-[(3-aminonaphthalene-2-carbonyl)amino]-3-phenylmethoxybutanoate
• CAS: 887246-25-5
• 化学式: C₂₃H₂₄N₂O₄
• 分子量: 392.455
• InChiKey: LKASLELFJNXAHK-VFNWGFHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl N-[(3-amino-2-naphthalenyl)carbonyl]-O-(phenylmethyl)-L-threoninate 、 2,4,6-三甲基苯基异氰酸酯 在 吡啶 作用下， 生成 methyl (2S,3R)-3-phenylmethoxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]butanoate
  参考文献：
  名称：

  Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues

  摘要：

  Optimization of the amino acid residue of a series of anthranilimide-based glycogen phosphorylase inhibitors is described leading to the identification of serine and threonine ether analogs. t-Butylthreonine analog 20 displayed potent in vitro inhibition of GPa, low potential for P450 inhibition, and excellent pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.084
• 作为产物：
  描述：

  3-氨基-2-萘甲酸 、 (2S,3R)-O-苄基-苏氨酸甲酯 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl N-[(3-amino-2-naphthalenyl)carbonyl]-O-(phenylmethyl)-L-threoninate
  参考文献：
  名称：

  Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues

  摘要：

  Optimization of the amino acid residue of a series of anthranilimide-based glycogen phosphorylase inhibitors is described leading to the identification of serine and threonine ether analogs. t-Butylthreonine analog 20 displayed potent in vitro inhibition of GPa, low potential for P450 inhibition, and excellent pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.084

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。
• Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues
  作者：Steven M. Sparks、Pierette Banker、David M. Bickett、Daphne C. Clancy、Scott H. Dickerson、Dulce M. Garrido、Pamela L. Golden、Andrew J. Peat、Lauren R. Sheckler、Francis X. Tavares、Stephen A. Thomson、James E. Weiel

  DOI：10.1016/j.bmcl.2008.11.084

  日期：2009.2

  Optimization of the amino acid residue of a series of anthranilimide-based glycogen phosphorylase inhibitors is described leading to the identification of serine and threonine ether analogs. t-Butylthreonine analog 20 displayed potent in vitro inhibition of GPa, low potential for P450 inhibition, and excellent pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.