N-[3-(3-phenylmethoxyphenyl)propyl]cyclohexanamine | 946198-37-4

• 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: N-[3-(3-phenylmethoxyphenyl)propyl]cyclohexanamine
• CAS: 946198-37-4
• 化学式: C₂₂H₂₉NO
• 分子量: 323.478
• InChiKey: HINCIIBCXUGNKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-[3-(3-phenylmethoxyphenyl)propyl]cyclohexanamine 、 Boc-beta-丙氨酸 在 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以96%的产率得到tert-butyl (3-((3-(3-(benzyloxy)phenyl)propyl)(cyclohexyl)amino)-3-oxopropyl)carbamate
  参考文献：
  名称：

  Macrocyclic BACE inhibitors: Optimization of a micromolar hit to nanomolar leads

  摘要：

  We have identified macrocyclic inhibitors of the aspartic protease BACE, implicated in the etiology of Alzheimer's disease. An X-ray structure of screening hit 1 in the BACE active site revealed a hairpin conformation suggesting that constrained macrocyclic derivatives may also bind there. Several of the analogs we prepared were >100x more potent than 1, such as 7 (5 nM K(i)). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.097
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以72%的产率得到N-[3-(3-phenylmethoxyphenyl)propyl]cyclohexanamine
  参考文献：
  名称：

  Macrocyclic BACE inhibitors: Optimization of a micromolar hit to nanomolar leads

  摘要：

  We have identified macrocyclic inhibitors of the aspartic protease BACE, implicated in the etiology of Alzheimer's disease. An X-ray structure of screening hit 1 in the BACE active site revealed a hairpin conformation suggesting that constrained macrocyclic derivatives may also bind there. Several of the analogs we prepared were >100x more potent than 1, such as 7 (5 nM K(i)). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.097

文献信息

• Macrocyclic BACE inhibitors: Optimization of a micromolar hit to nanomolar leads
  作者：Yifang Huang、Eric D. Strobel、Chih Y. Ho、Charles H. Reynolds、Kelly A. Conway、Jennifer A. Piesvaux、Douglas E. Brenneman、George J. Yohrling、H. Moore Arnold、Daniel Rosenthal、Richard S. Alexander、Brett A. Tounge、Marc Mercken、Marc Vandermeeren、Michael H. Parker、Allen B. Reitz、Ellen W. Baxter

  DOI：10.1016/j.bmcl.2010.03.097

  日期：2010.5

  We have identified macrocyclic inhibitors of the aspartic protease BACE, implicated in the etiology of Alzheimer's disease. An X-ray structure of screening hit 1 in the BACE active site revealed a hairpin conformation suggesting that constrained macrocyclic derivatives may also bind there. Several of the analogs we prepared were >100x more potent than 1, such as 7 (5 nM K(i)). (C) 2010 Elsevier Ltd. All rights reserved.