3-(4-(2-aminobenzoyl)-1H-1,2,3-triazol-1-yl)benzonitrile | 1437325-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-(2-aminobenzoyl)-1H-1,2,3-triazol-1-yl)benzonitrile
• 英文别名: 3-[4-(2-Aminobenzoyl)triazol-1-yl]benzonitrile；3-[4-(2-aminobenzoyl)triazol-1-yl]benzonitrile
• CAS: 1437325-83-1
• 化学式: C₁₆H₁₁N₅O
• 分子量: 289.296
• InChiKey: DVZHGHIYWRPKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-nitrophenyl)prop-2-yn-1-ol 在 manganese(IV) oxide 、 palladium 10% on activated carbon 、 氢气 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 3-(4-(2-aminobenzoyl)-1H-1,2,3-triazol-1-yl)benzonitrile
  参考文献：
  名称：

  1-Phenyl-4-benzoyl-1H-1,2,3-triazoles as Orally Bioavailable Transcriptional Function Suppressors of Estrogen-Related Receptor α

  摘要：

  Estrogen-related receptor a is a potential candidate target for therapeutic treatment of breast cancer. We describe the discovery and structure activity relationship study of a series of 1-phenyl-4-benzoyl-1H-1,2,3-triazoles as novel suppressors of ERR alpha transcriptional functions. The most promising compound, 2-aminophenyl-(1-(3-isopropylpheny1)-1H-1,2,3-triazol-4-yl)methanone (14n), potently suppressed the transcriptional functions of ERR alpha with IC50 = 0.021 mu M in a cell-based reporter gene assay and also decreased both the mRNA levels and the protein levels of ERR alpha and the downstream targets. This compound inhibited the proliferation and migration of breast cancer cells with high level of ERR alpha. Preliminary pharmacolcinetic studies suggested that it possessed a good pharmacokinetic profile with an oral bioavailability of 71.8%. The compounds may serve as novel small molecule probes for further validation of ERR alpha as a molecular target for anticancer drug development.

  DOI：

  10.1021/jm4003928

文献信息

• 1-Phenyl-4-benzoyl-1<i>H</i>-1,2,3-triazoles as Orally Bioavailable Transcriptional Function Suppressors of Estrogen-Related Receptor α
  作者：Shilin Xu、Xiaoxi Zhuang、Xiaofen Pan、Zhang Zhang、Lei Duan、Yingxue Liu、Lianwen Zhang、Xiaomei Ren、Ke Ding

  DOI：10.1021/jm4003928

  日期：2013.6.13

  Estrogen-related receptor a is a potential candidate target for therapeutic treatment of breast cancer. We describe the discovery and structure activity relationship study of a series of 1-phenyl-4-benzoyl-1H-1,2,3-triazoles as novel suppressors of ERR alpha transcriptional functions. The most promising compound, 2-aminophenyl-(1-(3-isopropylpheny1)-1H-1,2,3-triazol-4-yl)methanone (14n), potently suppressed the transcriptional functions of ERR alpha with IC50 = 0.021 mu M in a cell-based reporter gene assay and also decreased both the mRNA levels and the protein levels of ERR alpha and the downstream targets. This compound inhibited the proliferation and migration of breast cancer cells with high level of ERR alpha. Preliminary pharmacolcinetic studies suggested that it possessed a good pharmacokinetic profile with an oral bioavailability of 71.8%. The compounds may serve as novel small molecule probes for further validation of ERR alpha as a molecular target for anticancer drug development.