3-[(4-苯基苯基)氨基]丙酸 | 144653-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[(4-苯基苯基)氨基]丙酸
• 中文别名: N-联苯基-4-基-β-丙氨酸
• 英文名称: 3-(4-biphenylamino)propanoic acid
• 英文别名: 3-([1,1'-Biphenyl]-4-ylamino)propanoic acid；3-(4-phenylanilino)propanoic acid
• CAS: 144653-45-2
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: URQKONWODPRUBS-UHFFFAOYSA-N

物化性质

• 沸点：
  469.9±38.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  3-[(4-苯基苯基)氨基]丙酸 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 ethyl 4-(3-([1,1'-biphenyl]-4-yl(4-fluorobenzyl)amino)propanamido)benzoate
  参考文献：
  名称：

  Discovery of novel N,N-3-phenyl-3-benzylaminopropionanilides as potent inhibitors of cholesteryl ester transfer protein in vivo

  摘要：

  Epidemiological studies have identified that the risk of cardiovascular events increases due to the decreased levels of high density lipoprotein-cholesterol and the elevated levels of low density lipoprotein-cholesterol. Herein, we report a novel series of N,N-3-phenyl-3-benzylaminopropionanilide derivatives, which were identified as potent cholesteryl ester transfer protein (CETP) inhibitor. The initial lead compound L10 (IC50 8.06 mu M) was found by pharmacophore-based virtual screening (Dong-Mei Zhao et al., Chin. Chem. Lett. 2014, 25, 299). After systematic structure variation and biological testing against CETP, two different series were identified as scaffolds for potent CETP inhibitors. One is N,N-3-phenyl-3-benzylaminopropanamide derivatives, which were investigated in our previous paper (Bioorg. Med. Chem. 2015, doi: http://dx.doi.org/10.1016/j.bmc.2015.12.010). The most potent compound HL16 in that series has the IC50 of 0.69 mu M. The other series is N, N-3-phenyl-3-benzylaminopropionanilide derivatives, which was investigated in current study. Further optimization of the structure-activity relationship (SAR) resulted in H16 (IC50 0.15 mu M), which was discovered as a potent CETP inhibitor in vitro by BODIPY-CE fluorescence assay. In addition, the results of pharmacodynamics studies showed that H16 exhibited both favorable HDL-C enhancement and LDL-C reduction in vivo by hamster. It also has an excellent stability in rat liver microsomal. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.002
• 作为产物：
  描述：

  4-氨基联苯 、 丙烯酸 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 3-[(4-苯基苯基)氨基]丙酸
  参考文献：
  名称：

  Discovery of novel N,N-3-phenyl-3-benzylaminopropionanilides as potent inhibitors of cholesteryl ester transfer protein in vivo

  摘要：

  Epidemiological studies have identified that the risk of cardiovascular events increases due to the decreased levels of high density lipoprotein-cholesterol and the elevated levels of low density lipoprotein-cholesterol. Herein, we report a novel series of N,N-3-phenyl-3-benzylaminopropionanilide derivatives, which were identified as potent cholesteryl ester transfer protein (CETP) inhibitor. The initial lead compound L10 (IC50 8.06 mu M) was found by pharmacophore-based virtual screening (Dong-Mei Zhao et al., Chin. Chem. Lett. 2014, 25, 299). After systematic structure variation and biological testing against CETP, two different series were identified as scaffolds for potent CETP inhibitors. One is N,N-3-phenyl-3-benzylaminopropanamide derivatives, which were investigated in our previous paper (Bioorg. Med. Chem. 2015, doi: http://dx.doi.org/10.1016/j.bmc.2015.12.010). The most potent compound HL16 in that series has the IC50 of 0.69 mu M. The other series is N, N-3-phenyl-3-benzylaminopropionanilide derivatives, which was investigated in current study. Further optimization of the structure-activity relationship (SAR) resulted in H16 (IC50 0.15 mu M), which was discovered as a potent CETP inhibitor in vitro by BODIPY-CE fluorescence assay. In addition, the results of pharmacodynamics studies showed that H16 exhibited both favorable HDL-C enhancement and LDL-C reduction in vivo by hamster. It also has an excellent stability in rat liver microsomal. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.002

文献信息

• BIPHENYL HYDROXAMATE INHIBITORS OF MATRIX METALLOPROTEINASES
  申请人：Abbott Laboratories

  公开号：EP0874808A1

  公开（公告）日：1998-11-04
• US5480871A
  申请人：——

  公开号：US5480871A

  公开（公告）日：1996-01-02
• US5665777A
  申请人：——

  公开号：US5665777A

  公开（公告）日：1997-09-09
• [EN] PEPTOID ALPHA-1 ADRENERGIC RECEPTOR LIGANDS<br/>[FR] LIGANDS DU RECEPTEUR ALPHA-1 ADRENERGIQUE PEPTOÏDIQUE
  申请人：CHIRON CORPORATION

  公开号：WO1995004072A1

  公开（公告）日：1995-02-09

  (EN) Compounds of formula (1) are useful for treating conditions modulated by $g(a)1-adrenergic receptors.(FR) Les composés de la formule (1) sont utilisés pour traiter des états modulés par les récepteurs $g(a)1-adrénergiques.
• [EN] OPIATE RECEPTOR LIGANDS<br/>[FR] LIGANDS DE RECEPTEURS D'OPIACES
  申请人：CHIRON CORPORATION

  公开号：WO1995027729A1

  公开（公告）日：1995-10-19

  (EN) Compounds of formula (1) bind opioid receptors wherein X and Y are each independently (2).(FR) Composés représentés par la formule (1) et se fixant à des récepteurs d'opioïdes, dans laquelle X et Y sont chacun indépendamment (2).