6-(4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)hexanoic acid | 1023694-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-(4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)hexanoic acid
• CAS: 1023694-88-3
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: RJWRDUOIXUVYPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.05
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)hexanoic acid 、 1,8-二氨基萘 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以41%的产率得到N-(8-aminonaphthalen-1-yl)-6-[6-oxo-4-(4-phenylphenyl)-1H-pyrimidin-2-yl]hexanamide
  参考文献：
  名称：

  Novel uracil-based 2-aminoanilide and 2-aminoanilide-like derivatives: Histone deacetylase inhibition and in-cell activities

  摘要：

  A novel series of non-hydroxamate HDAC inhibitors (HDACi) showing a uracil group at the left and a 2-aminoanilide/2-aminoanilide- like portion at the right head have been reported. In particular, the new compounds incorporating a 2-aminoanilide moiety behaved as class I-selective HDACi. Compound 8, the most potent and class I-selective, showed weak apoptosis (higher than MS-275) joined to cytodifferentiating activity on U937 cells. Surprisingly, the highest differentiation was observed with 13, through an effect that seems to be unrelated to HDAC inhibition. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.055
• 作为产物：
  描述：

  庚二酸二乙酯 、 3-amino-3-(biphenyl-4-yl)acrylamide 在 sodium 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以67%的产率得到6-(4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)hexanoic acid
  参考文献：
  名称：

  Novel uracil-based 2-aminoanilide and 2-aminoanilide-like derivatives: Histone deacetylase inhibition and in-cell activities

  摘要：

  A novel series of non-hydroxamate HDAC inhibitors (HDACi) showing a uracil group at the left and a 2-aminoanilide/2-aminoanilide- like portion at the right head have been reported. In particular, the new compounds incorporating a 2-aminoanilide moiety behaved as class I-selective HDACi. Compound 8, the most potent and class I-selective, showed weak apoptosis (higher than MS-275) joined to cytodifferentiating activity on U937 cells. Surprisingly, the highest differentiation was observed with 13, through an effect that seems to be unrelated to HDAC inhibition. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.055