(E)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-2-methylacrylaldehyde | 1375800-40-0

• 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: (E)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-2-methylacrylaldehyde
• CAS: 1375800-40-0
• 化学式: C₁₁H₈F₄O
• 分子量: 232.178
• InChiKey: NYEWCTHQEYAIMV-FARCUNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-2-methylacrylaldehyde 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 97.17h， 生成 (E)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-2-methyl-N-(2-(1-methylpyrrolidin-2-yl)ethyl)prop-2-en-1-amine
  参考文献：
  名称：

  Synthesis, modeling and functional activity of substituted styrene-amides as small-molecule CXCR7 agonists

  摘要：

  The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the beta-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate the pharmacology and the therapeutic potential of CXCR7. In the present study, we synthesized 24 derivatives based on a compound scaffold patented by Chemocentryx and obtained CXCR7 ligands with pK(i) values ranging from 5.3 to 8.1. SAR studies were supported by computational 3D Fingerprint studies, revealing several important affinity descriptors. Two key compounds (29 and 30, VUF11207 and VUF11403) were found to be high-potency ligands that induce recruitment of beta-arrestin2 and subsequent internalization of CXCR7, making them important tool compounds in future CXCR7 research. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.041
• 作为产物：
  描述：

  丙醛 、 3-氟-5-(三氟甲基)苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以65%的产率得到(E)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-2-methylacrylaldehyde
  参考文献：
  名称：

  Synthesis, modeling and functional activity of substituted styrene-amides as small-molecule CXCR7 agonists

  摘要：

  The chemokine receptor CXCR7 is an atypical G protein-coupled receptor as it preferentially signals through the beta-arrestin pathway rather than through G proteins. CXCR7 is thought to be of importance in cancer and the development of CXCR7-targeting ligands is of huge importance to further elucidate the pharmacology and the therapeutic potential of CXCR7. In the present study, we synthesized 24 derivatives based on a compound scaffold patented by Chemocentryx and obtained CXCR7 ligands with pK(i) values ranging from 5.3 to 8.1. SAR studies were supported by computational 3D Fingerprint studies, revealing several important affinity descriptors. Two key compounds (29 and 30, VUF11207 and VUF11403) were found to be high-potency ligands that induce recruitment of beta-arrestin2 and subsequent internalization of CXCR7, making them important tool compounds in future CXCR7 research. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.041