thiazole-2-carboxylic acid [4-(2,4-dimethylphenyl)thiazol-2-yl]amide | 1134986-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: thiazole-2-carboxylic acid [4-(2,4-dimethylphenyl)thiazol-2-yl]amide
• 英文别名: N-[4-(2,4-dimethylphenyl)-1,3-thiazol-2-yl]-1,3-thiazole-2-carboxamide
• CAS: 1134986-16-5
• 化学式: C₁₅H₁₃N₃OS₂
• 分子量: 315.42
• InChiKey: LSIVUAMNFIRXAP-UHFFFAOYSA-N

物化性质

• 熔点：
  146.5-147.5 °C
• 密度：
  1.362±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-噻唑-2-甲酰氯 、 4-(2,4-二甲基-苯基)-噻唑-2-亚胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到thiazole-2-carboxylic acid [4-(2,4-dimethylphenyl)thiazol-2-yl]amide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Series of Novel Inhibitor of Nek2/Hec1 Analogues

  摘要：

  High expression in cancer 1 (Hec1) is an oncogene overly expressed in many human cancers. Small molecule inhibitor of Nek2/Hcc1 (INH) targeting the Heel and its regulator, Nek2, in the mitotic pathway, was identified to inactivate Hec1/Nek2 function mediated by protein degradation that subsequently leads to chromosome mis-segregation and cell death. To further improve the efficacy of INH, a series of INH analogues were designed, synthesized, and evaluated. Among these 33 newly synthesized analogues, three of them, 6, 13, and 21, have 6-8 fold more potent cell killing activity than the previous lead compound INH1. Compounds 6 and 21 were chosen for analyzing the underlying action mechanism. They target directly the Hec1/Nek2 pathway and cause chromosome mis-alignment as well as cell death, a mechanism similar to that of INH1, This initial exploration of structural/functional relationship of INH may advance the progress for developing clinically applicable INH analogue.

  DOI：

  10.1021/jm8015969