Methyl 2,4-dioxo-4-(2,4,5-trifluorophenyl)butanoate | 1119299-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,4-dioxo-4-(2,4,5-trifluorophenyl)butanoate
• CAS: 1119299-58-9
• 化学式: C₁₁H₇F₃O₄
• 分子量: 260.169
• InChiKey: AXDKQFYCIVABNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 2,4-dioxo-4-(2,4,5-trifluorophenyl)butanoate 在 溶剂黄146 、 肼 作用下， 反应 12.0h， 生成 methyl 3-(2,4,5-trifluorophenyl)-1H-pyrazole-5-carboxylate
  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：

  草酸二甲酯 、 2',4',5'-三氟苯乙酮 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 Methyl 2,4-dioxo-4-(2,4,5-trifluorophenyl)butanoate
  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

文献信息

• Design and synthesis of pyrazole derivatives as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP)
  作者：Shyama Sidique、Robert Ardecky、Ying Su、Sonoko Narisawa、Brock Brown、José Luis Millán、Eduard Sergienko、Nicholas D.P. Cosford

  DOI：10.1016/j.bmcl.2008.10.107

  日期：2009.1

  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.