7-(3-{1-[2-(3-bromophenyl)-2-hydroxyethyl]-1H-[1,2,3]triazol-4-yl}phenylcarbamoyl)heptanoic acid methyl ester | 1033391-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-(3-{1-[2-(3-bromophenyl)-2-hydroxyethyl]-1H-[1,2,3]triazol-4-yl}phenylcarbamoyl)heptanoic acid methyl ester
• CAS: 1033391-43-3
• 化学式: C₂₅H₂₉BrN₄O₄
• 分子量: 529.434
• InChiKey: VFXGBNRTIUFBLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106.34
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  7-(3-{1-[2-(3-bromophenyl)-2-hydroxyethyl]-1H-[1,2,3]triazol-4-yl}phenylcarbamoyl)heptanoic acid methyl ester 在 氢氧化钾 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以56%的产率得到octanedioic acid (3-{1-[2-(3-bromophenyl)-2-hydroxyethyl]-1H-[1,2,3]triazol-4-yl}phenyl)amide hydroxyamide
  参考文献：
  名称：

  A Series of Potent and Selective, Triazolylphenyl-Based Histone Deacetylases Inhibitors with Activity against Pancreatic Cancer Cells and Plasmodium falciparum

  摘要：

  The discovery of the rules governing the inhibition of the various HDAC isoforms is likely to be key to identifying improved therapeutics that act as epigenetic modulators of gene transcription. Herein we present results on the modification of the CAP region of a set of triazolylphenyl-based HDACIs, and show that the nature of substitution on the phenyl ring plays a role in their selectivity for HDAC1 versus HDAC6, with low to moderate selectivity (2-51-fold) being achieved. In light of the valuable selectivity and potency that were identified for the triazolylphenyl ligand 6b in the inhibition of HDAC6 (IC50 = 1.9 nM), this compound represents a valuable research tool and a candidate for further chemical modifications. Lastly, these new HDACIs were studied for both their anticancer and antimalarial activity, which serve to validate the superior activity of the HDACI 10c.

  DOI：

  10.1021/jm701606b
• 作为产物：
  描述：

  2-azido-1-(3-bromophenyl)ethan-1-ol 、 7-(3-乙炔基苯基氨基甲酰基)庚酸甲酯 在 copper(ll) sulfate pentahydrate 、 ascorbic acid sodium salt 作用下， 以 乙醇 、 水 为溶剂， 以71%的产率得到7-(3-{1-[2-(3-bromophenyl)-2-hydroxyethyl]-1H-[1,2,3]triazol-4-yl}phenylcarbamoyl)heptanoic acid methyl ester
  参考文献：
  名称：

  A Series of Potent and Selective, Triazolylphenyl-Based Histone Deacetylases Inhibitors with Activity against Pancreatic Cancer Cells and Plasmodium falciparum

  摘要：

  The discovery of the rules governing the inhibition of the various HDAC isoforms is likely to be key to identifying improved therapeutics that act as epigenetic modulators of gene transcription. Herein we present results on the modification of the CAP region of a set of triazolylphenyl-based HDACIs, and show that the nature of substitution on the phenyl ring plays a role in their selectivity for HDAC1 versus HDAC6, with low to moderate selectivity (2-51-fold) being achieved. In light of the valuable selectivity and potency that were identified for the triazolylphenyl ligand 6b in the inhibition of HDAC6 (IC50 = 1.9 nM), this compound represents a valuable research tool and a candidate for further chemical modifications. Lastly, these new HDACIs were studied for both their anticancer and antimalarial activity, which serve to validate the superior activity of the HDACI 10c.

  DOI：

  10.1021/jm701606b