octanedioic acid (2-aminophenyl)amide [3-(1-phenyl-1H-[1,2,3]triazol-4-yl)phenyl]amide | 1169826-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: octanedioic acid (2-aminophenyl)amide [3-(1-phenyl-1H-[1,2,3]triazol-4-yl)phenyl]amide
• 英文别名: N'-(2-aminophenyl)-N-[3-(1-phenyltriazol-4-yl)phenyl]octanediamide
• CAS: 1169826-27-0
• 化学式: C₂₈H₃₀N₆O₂
• 分子量: 482.585
• InChiKey: XFBZAGGLERWKQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-[3-(1-phenyl-1H-[1,2,3]triazol-4-yl)phenylcarbamoyl]heptanoic acid 、 邻苯二胺 在 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以34%的产率得到octanedioic acid (2-aminophenyl)amide [3-(1-phenyl-1H-[1,2,3]triazol-4-yl)phenyl]amide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Triazol-4-ylphenyl-Bearing Histone Deacetylase Inhibitors as Anticancer Agents

  摘要：

  Our triazole-based histone deacetylase inhibitor (HDACI), octanedioic acid hydroxyamide[3-(1-phenyl-1H-[1,2,3]triazol-4-yl)phenyl]amide (4a), suppresses pancreatic cancer cell growth in vitro with the lowest IC50 value of 20 nM against MiaPaca-2 cell. In this study, we continued our efforts to develop triazol-4-ylphenyl bearing hydroxamate analogues by embellishing the terminal phenyl ring of 4a with different substituents. The isoform inhibitory profile of these hydroxamate analogues was similar to those of 4a. All of these triazol-4-ylphenyl bearing hydroxamates are pan-HDACIs like SAHA. Moreover, compounds 4h and 11a were found to be very effective inhibitors of cancer cell growth in the HupT3 (IC50 = 50 nM) and MiaPaca-2 (IC50 = 40 nM) cancer cell lines, respectively. Compound 4a was found to reactivate the expression of CDK inhibitor proteins and to suppress pancreatic cancer cell growth in vivo. Taken together, these data further support the value of the triazol-4-ylphenyl bearing hydroxamates in identifying potential pancreatic cancer therapies.

  DOI：

  10.1021/jm901667k