2,3,4,5-四氢-1H-1,4-苯二氮杂-1-甲酸叔丁酯 | 1087800-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 2,3,4,5-四氢-1H-1,4-苯二氮杂-1-甲酸叔丁酯
• 英文名称: tert-butyl 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-1-carboxylate
• 英文别名: tert-butyl 2,3,4,5-tetrahydro-1,4-benzodiazepine-1-carboxylate
• CAS: 1087800-69-8
• 化学式: C₁₄H₂₀N₂O₂
• mdl: MFCD11505642
• 分子量: 248.325
• InChiKey: REGZHFPHDGBZJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 2,3,4,5-四氢-1H-1,4-苯二氮杂-1-甲酸叔丁酯 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 8-N-(cyclopropylmethyl)-4-N-(2-methylsulfanylphenyl)-2-(1,2,3,5-tetrahydro-1,4-benzodiazepin-4-yl)pyrimido[5,4-d]pyrimidine-4,8-diamine
  参考文献：
  名称：

  Pyrimidinopyrimidine inhibitors of ketohexokinase: Exploring the ring C2 group that interacts with Asp-27B in the ligand binding pocket

  摘要：

  Inhibitors of ketohexokinase (KHK) have potential for the treatment of diabetes and obesity. We have continued studies on a pyrimidinopyrimidine series of potent KHK inhibitors by exploring the 2-position substituent (R-3) that interacts with Asp-27B in the ATP-binding region of KHK (viz. 1, 2; Table 1). We found that increased spacing between the terminal ammonium group and the heterocyclic scaffold (viz. 16-20), such that interaction with Asp-27B is not possible, still results in potent KHK inhibition (IC50 = 15-50 nM). We propose a new interaction with Asp-194, which serves to expand the pyrimidinopyrimidine pharmacophore. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.008

文献信息

• Pyrimidinopyrimidine inhibitors of ketohexokinase: Exploring the ring C2 group that interacts with Asp-27B in the ligand binding pocket
  作者：Bruce E. Maryanoff、John C. O’Neill、David F. McComsey、Stephen C. Yabut、Diane K. Luci、Alan C. Gibbs、Margery A. Connelly

  DOI：10.1016/j.bmcl.2012.06.008

  日期：2012.8

  Inhibitors of ketohexokinase (KHK) have potential for the treatment of diabetes and obesity. We have continued studies on a pyrimidinopyrimidine series of potent KHK inhibitors by exploring the 2-position substituent (R-3) that interacts with Asp-27B in the ATP-binding region of KHK (viz. 1, 2; Table 1). We found that increased spacing between the terminal ammonium group and the heterocyclic scaffold (viz. 16-20), such that interaction with Asp-27B is not possible, still results in potent KHK inhibition (IC50 = 15-50 nM). We propose a new interaction with Asp-194, which serves to expand the pyrimidinopyrimidine pharmacophore. (C) 2012 Elsevier Ltd. All rights reserved.