4-[5-(1,3-Benzodioxol-5-yl)-1-[2-(trifluoromethyl)phenyl]pyrazol-3-yl]benzamide | 957653-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[5-(1,3-Benzodioxol-5-yl)-1-[2-(trifluoromethyl)phenyl]pyrazol-3-yl]benzamide
• CAS: 957653-21-3
• 化学式: C₂₄H₁₆F₃N₃O₃
• 分子量: 451.405
• InChiKey: KJPKSLDPCYUJQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(5-(benzo[d][1,3]dioxol-5-yl)-1-(2-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)benzonitrile 在 potassium hydroxide 、 叔丁醇 作用下， 生成 4-[5-(1,3-Benzodioxol-5-yl)-1-[2-(trifluoromethyl)phenyl]pyrazol-3-yl]benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,2,4-trisubstituted imidazoles and 1,3,5-trisubstituted pyrazoles as inhibitors of transforming growth factor β type 1 receptor (ALK5)

  摘要：

  Two series of nitrogenous heterocycle compounds-1,2,4-trisubstituted imidazoles and 1,3,5-trisubstituted pyrazoles have been synthesized and evaluated for their ALK5 inhibitory activity and cytotoxicity in TGF beta-Smad2 assay and MTT assay, respectively. The ALK4/5/7 inhibitory activity of some compound was also evaluated in ALK4/5/7 autophosphorylation assays. Compounds 6c and 14c showed relatively potent ALK5 inhibition while weak cytotoxicity. At the same time, compounds 6c and 14c display relatively better ALK5 selectivity versus ALK4/ALK7 (nearly 10-fold) compared with SB431542, a well known ALK5 inhibitor. Compound 6g2 proved to be a moderately selective ALK4 inhibitor versus ALK5 and ALK7 (>10-fold). The binding mode of 14c generated by flexible docking study shows that 14c fits well into the site cavity of ALK5 by forming several tight interactions. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.04.066