3-(2,3,4-trichlorophenyl)-1H-pyrazole-5-carboxylic acid | 1039041-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2,3,4-trichlorophenyl)-1H-pyrazole-5-carboxylic acid
• CAS: 1039041-59-2
• 化学式: C₁₀H₅Cl₃N₂O₂
• 分子量: 291.521
• InChiKey: GVLDGHBEZZFUJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,3,4-trichlorophenyl)-1H-pyrazole-5-carboxylic acid 、 C.I.酸性橙108 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以80%的产率得到N-(2-hydroxyethyl)-3-(2,3,4-trichlorophenyl)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Design and synthesis of pyrazole derivatives as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP)

  摘要：

  Tissue-nonspecific alkaline phosphatase (TNAP) plays a central role in regulating extracellular matrix calcification during bone formation and growth. High-throughput screening (HTS) for small molecule TNAP inhibitors led to the identification of hits in the sub-micromolar potency range. We report the design, synthesis and in vitro evaluation of a series of pyrazole derivatives of a screening hit which are potent TNAP inhibitors exhibiting IC50 values as low as 5 nM. A representative of the series was characterized in kinetic studies and determined to have a mode of inhibition not previously observed for TNAP inhibitors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.107
• 作为产物：
  描述：

  methyl 3-(2,3,4-trichlorophenyl)-1H-pyrazole-5-carboxylate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以96%的产率得到3-(2,3,4-trichlorophenyl)-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of pyrazole derivatives as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP)

  摘要：

  Tissue-nonspecific alkaline phosphatase (TNAP) plays a central role in regulating extracellular matrix calcification during bone formation and growth. High-throughput screening (HTS) for small molecule TNAP inhibitors led to the identification of hits in the sub-micromolar potency range. We report the design, synthesis and in vitro evaluation of a series of pyrazole derivatives of a screening hit which are potent TNAP inhibitors exhibiting IC50 values as low as 5 nM. A representative of the series was characterized in kinetic studies and determined to have a mode of inhibition not previously observed for TNAP inhibitors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.107