5-((4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)thio)pentanoic acid | 1023694-81-6

• 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: 5-((4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)thio)pentanoic acid
• 英文别名: 5-[[6-oxo-4-(4-phenylphenyl)-1H-pyrimidin-2-yl]sulfanyl]pentanoic acid
• CAS: 1023694-81-6
• 化学式: C₂₁H₂₀N₂O₃S
• 分子量: 380.467
• InChiKey: VIZZRYKYDZKDAS-UHFFFAOYSA-N

物化性质

• 沸点：
  607.1±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-((4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)thio)pentanoic acid 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.17h， 生成 MC1742
  参考文献：
  名称：

  Novel Histone Deacetylase Inhibitors Induce Growth Arrest, Apoptosis, and Differentiation in Sarcoma Cancer Stem Cells

  摘要：

  Musculoskeletal sarcomas are aggressive malignancies of bone and soft tissues often affecting, children and adolescents. Histone deacetylase inhibitors (HDACi) have been proposed to counteract Cancer stem cells (CSCs) in solid neoplasms. When tested in human osteosarcoma, rhabdomyosarcoma, and Ewing's sarcoma Stem cells, the new HDACi MC1742 (1) and MC2625 (2) increased acetyl-H3 and acetyl-tubulin levels and inhibited CSC growth by apoptosis induction. At nontoxic doses, 1 promoted osteogenic differentiation. Further investigation with 1 will be done in prolinical sarcoma model.

  DOI：

  10.1021/acs.jmedchem.5b00126
• 作为产物：
  描述：

  ethyl 5-(4-(biphenyl-4-yl)-6-oxo-1,6-dihydropyrimidin-2-ylthio)pentanoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以90%的产率得到5-((4-([1,1'-biphenyl]-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)thio)pentanoic 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