1,3-bis(3-formylphenyl)imidazolidin-2-one | 1428236-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1,3-bis(3-formylphenyl)imidazolidin-2-one
• CAS: 1428236-79-6
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: QKAWZFPXZZLMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(3-formylphenyl)imidazolidin-2-one 在 N,N-二甲基丙烯基脲 、 正丁基锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 19.5h， 生成 (E)-3-[3-[3-[3-[(E)-2-carboxyethenyl]phenyl]-2-oxoimidazolidin-1-yl]phenyl]prop-2-enoic acid
  参考文献：
  名称：

  Novel symmetrical ureas as modulators of protein arginine methyl transferases

  摘要：

  Methylation of histone arginine residues is an epigenetic mark related to gene expression that is implicated in a variety of biological processes and can be reversed by small-molecule modulators of protein arginine methyltransferases (PRMTs). A series of symmetrical ureas, designed as analogues of the known PRMT1 inhibitor AMI-1 have been synthesized using Pd-catalyzed Ar-N amide bond formation processes or carbonylation reactions as key steps. Their inhibitory profile has been characterized. The enzymatic assays showed a weak effect on PRMT1 and PRMT5 activity for most of the compounds. The acyclic urea that exhibited the strongest effect on the inhibition of the PRMT1 activity also showed the greatest effect on the expression of some androgen receptor target genes (TMPRSS2 and FKBP5), which may be related with its enzymatic activity. Surprisingly, AMI-1 behaved as an activator of PRMT5 activity, a result not reported so far. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.017
• 作为产物：
  描述：

  2-咪唑烷酮 、 间溴苯甲醛 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以91%的产率得到1,3-bis(3-formylphenyl)imidazolidin-2-one
  参考文献：
  名称：

  Novel symmetrical ureas as modulators of protein arginine methyl transferases

  摘要：

  Methylation of histone arginine residues is an epigenetic mark related to gene expression that is implicated in a variety of biological processes and can be reversed by small-molecule modulators of protein arginine methyltransferases (PRMTs). A series of symmetrical ureas, designed as analogues of the known PRMT1 inhibitor AMI-1 have been synthesized using Pd-catalyzed Ar-N amide bond formation processes or carbonylation reactions as key steps. Their inhibitory profile has been characterized. The enzymatic assays showed a weak effect on PRMT1 and PRMT5 activity for most of the compounds. The acyclic urea that exhibited the strongest effect on the inhibition of the PRMT1 activity also showed the greatest effect on the expression of some androgen receptor target genes (TMPRSS2 and FKBP5), which may be related with its enzymatic activity. Surprisingly, AMI-1 behaved as an activator of PRMT5 activity, a result not reported so far. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.017