N-[5-bromo-2-(2-morpholinoethoxy)phenyl]-3-phenylpropanamide | 1101858-61-0

• 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-[5-bromo-2-(2-morpholinoethoxy)phenyl]-3-phenylpropanamide
• 英文别名: N-[5-bromo-2-(2-morpholin-4-ylethoxy)phenyl]-3-phenylpropanamide
• CAS: 1101858-61-0
• 化学式: C₂₁H₂₅BrN₂O₃
• 分子量: 433.345
• InChiKey: IWTLCHDPVYLFCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-bromo-2-(2-morpholinoethoxy)benzenamine 、 3-苯丙酰氯 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到N-[5-bromo-2-(2-morpholinoethoxy)phenyl]-3-phenylpropanamide
  参考文献：
  名称：

  Identification of pharmacophore model, synthesis and biological evaluation of N-phenyl-1-arylamide and N-phenylbenzenesulfonamide derivatives as BACE 1 inhibitors

  摘要：

  The pharmacophore model of arylpiperazine amide derivatives was built using Discovery Studio 2.0 software package and the best pharmacophore model ( Hypo 1) was validated by Enrichment and ROC method ( EF at 2%, 5% and 10% are 30.6, 12.2 and 7.7; AUC of the ROC curve is 0.93). According to the best pharmacophore model, 11 N-phenyl-1-arylamide, N-phenylbenzenesulfonamide derivatives, compounds 26-28, and 33a-g, were designed to be synthesized and their BACE 1 inhibitory activities were determined experimentally. Their theoretical results were in good agreement with the experimental values. Compound 33d, which displayed the highest BACE 1 activity (18.33 +/- 2.80 mu mol/L) among these two series, was chosen to study the protein binding pattern and the result showed that it was in close contact with two essential catalytic aspartates (Asp32 and Asp228) of the BACE 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.059

文献信息

• Identification of pharmacophore model, synthesis and biological evaluation of N-phenyl-1-arylamide and N-phenylbenzenesulfonamide derivatives as BACE 1 inhibitors
  作者：Wenhai Huang、Haiping Yu、Rong Sheng、Jia Li、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.10.059

  日期：2008.12.15

  The pharmacophore model of arylpiperazine amide derivatives was built using Discovery Studio 2.0 software package and the best pharmacophore model ( Hypo 1) was validated by Enrichment and ROC method ( EF at 2%, 5% and 10% are 30.6, 12.2 and 7.7; AUC of the ROC curve is 0.93). According to the best pharmacophore model, 11 N-phenyl-1-arylamide, N-phenylbenzenesulfonamide derivatives, compounds 26-28, and 33a-g, were designed to be synthesized and their BACE 1 inhibitory activities were determined experimentally. Their theoretical results were in good agreement with the experimental values. Compound 33d, which displayed the highest BACE 1 activity (18.33 +/- 2.80 mu mol/L) among these two series, was chosen to study the protein binding pattern and the result showed that it was in close contact with two essential catalytic aspartates (Asp32 and Asp228) of the BACE 1. (C) 2008 Elsevier Ltd. All rights reserved.