ethyl [4-(t-butoxycarbonylamino-methyl)-phenoxy]-acetate | 1041611-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl [4-(t-butoxycarbonylamino-methyl)-phenoxy]-acetate
• 英文别名: ethyl 2-[4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenoxy]acetate
• CAS: 1041611-86-2
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: ZVUQUUGDMKEVDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl [4-(t-butoxycarbonylamino-methyl)-phenoxy]-acetate 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-) 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成
  参考文献：
  名称：

  Discovering Novel α-aminoacyl-Containing Proline Derivatives with Potent and Selective Inhibitory Activity Against Dipeptidyl Peptidase IV: Design, Synthesis, Biological Evaluation, and Molecular Modeling

  摘要：

  On the basis of the enzyme‐binding features of known potent inhibitors of dipeptidyl peptidase IV, novel α‐aminoacyl‐containing proline analogs (8Aa–8Ak, 8Ba–8Bj, 8Ca–8Ck, and 8Da–8Di) with the S configuration were designed, synthesized, and their activity profiled. Their structural features were determined by nuclear magnetic resonance (NMR) spectroscopy, low‐ and high‐resolution mass spectroscopy. Five compounds (8Aa, 8Aj, 8Ch, 8Ck, and 8Dc) were shown to have promising inhibitory activities against dipeptidyl peptidase IV. Two of them, compounds 8Aa and 8Aj inhibited dipeptidyl peptidase IV with IC50 values of 4.56 and 8.4 μm, respectively, and displayed no inhibition at other dipeptidyl peptidase IV. The possible binding modes of compounds 6, 7, 8Aa, and 8Aj with dipeptidyl peptidase IV were also explored by molecular docking simulation. This study provides promising new templates for the further development of antidiabetic agents.

  DOI：

  10.1111/j.1747-0285.2012.01438.x
• 作为产物：
  描述：

  溴乙酸乙酯 、 4-[[叔丁氧酰胺]甲基]-苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以77%的产率得到ethyl [4-(t-butoxycarbonylamino-methyl)-phenoxy]-acetate
  参考文献：
  名称：

  THIAZOLIDINE DERIVATIVES AND METHODS FOR THE PREPARATION THEREOF

  摘要：

  本发明涉及具有β-氨基团的酰基链上的新型2-羰基-3-酰基-1,3-噻唑啉化合物，包括其自由形式、前药形式或其药用可接受盐，包括它们的对映体、异构体和消旋体，作为高效的DPP-IV抑制剂。该发明还涉及包含所述化合物的药物组合物。本发明还涉及制备所述化合物以及治疗DPP-IV介导的疾病的方法。

  公开号：

  US20100048570A1

文献信息

• THIAZOLIDINE DERIVATIVES AND METHODS FOR THE PREPARATION THEREOF
  申请人：Kim Sung Soo

  公开号：US20100048570A1

  公开（公告）日：2010-02-25

  The present invention relates to novel 2-carbonyl-3-acyl-1,3-thiazolidines having a β-amino group on the acyl chain, in free, prodrug form or pharmaceutically acceptable salt thereof, including their enantiomers, diastereomers and racemates, as efficient inhibitors against DPP-IV. The invention further relates to the pharmaceutical compositions comprising the disclosed compounds. The present invention also relates to methods for preparing the disclosed compounds and for treating DPP-IV-mediated diseases.

  本发明涉及具有β-氨基团的酰基链上的新型2-羰基-3-酰基-1,3-噻唑啉化合物，包括其自由形式、前药形式或其药用可接受盐，包括它们的对映体、异构体和消旋体，作为高效的DPP-IV抑制剂。该发明还涉及包含所述化合物的药物组合物。本发明还涉及制备所述化合物以及治疗DPP-IV介导的疾病的方法。
• Discovering Novel α-aminoacyl-Containing Proline Derivatives with Potent and Selective Inhibitory Activity Against Dipeptidyl Peptidase IV: Design, Synthesis, Biological Evaluation, and Molecular Modeling
  作者：Xiaodong Zhang、Jiang Wang、Mingbo Su、Zeng Li、Jingya Li、Jia Li、Hong Liu

  DOI：10.1111/j.1747-0285.2012.01438.x

  日期：2012.12

  On the basis of the enzyme‐binding features of known potent inhibitors of dipeptidyl peptidase IV, novel α‐aminoacyl‐containing proline analogs (8Aa–8Ak, 8Ba–8Bj, 8Ca–8Ck, and 8Da–8Di) with the S configuration were designed, synthesized, and their activity profiled. Their structural features were determined by nuclear magnetic resonance (NMR) spectroscopy, low‐ and high‐resolution mass spectroscopy. Five compounds (8Aa, 8Aj, 8Ch, 8Ck, and 8Dc) were shown to have promising inhibitory activities against dipeptidyl peptidase IV. Two of them, compounds 8Aa and 8Aj inhibited dipeptidyl peptidase IV with IC50 values of 4.56 and 8.4 μm, respectively, and displayed no inhibition at other dipeptidyl peptidase IV. The possible binding modes of compounds 6, 7, 8Aa, and 8Aj with dipeptidyl peptidase IV were also explored by molecular docking simulation. This study provides promising new templates for the further development of antidiabetic agents.