5-(6-氧代-4-苯基-1,6-二氢嘧啶-2-基硫代)戊酸 | 1023694-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(6-氧代-4-苯基-1,6-二氢嘧啶-2-基硫代)戊酸
• 英文名称: 5-(6-oxo-4-phenyl-1,6-dihydropyrimidin-2-ylthio)pentanoic acid
• CAS: 1023694-79-2
• 化学式: C₁₅H₁₆N₂O₃S
• 分子量: 304.37
• InChiKey: OAKWFKHGCIZVDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.05
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(6-氧代-4-苯基-1,6-二氢嘧啶-2-基硫代)戊酸 、 邻苯二胺 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58%的产率得到C₂₁H₂₂N₄O₂S
  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：

  ethyl 5-[(6-oxo-4-phenyl-1H-pyrimidin-2-yl)sulfanyl]pentanoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 5-(6-氧代-4-苯基-1,6-二氢嘧啶-2-基硫代)戊酸
  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