5-(2,4,5-Trifluorophenyl)-1H-pyrazole-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,4,5-Trifluorophenyl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 3-(2,4,5-trifluorophenyl)-1H-pyrazole-5-carboxylic acid
• 化学式: C₁₂₁H₁₄₄N₁₅O₂₃Pol
• 分子量: 242.15
• InChiKey: NDZOYBICQCIEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  6

反应信息

• 作为反应物：
  描述：

  5-(2,4,5-Trifluorophenyl)-1H-pyrazole-3-carboxylic acid 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以2.6 mg的产率得到1b-(LysPhe-NHAc)3
  参考文献：
  名称：

  三足支架分子在固体支架上的功能化

  摘要：

  描述了一种用于在固体支持物上对三足支架分子进行功能化的通用合成方法。研究了与将三脚架支架连接到树脂（例如单加合物与多加合物和分子内环化）相关的内在问题并提供了解决方案。合成方法依赖于在合成的关键步骤中使用特定的保护基团。然而，重要的是，支架分子上的保护基团从未使用过，这显着促进了支架变异，例如在组合研究中。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800259
• 作为产物：
  描述：

  methyl 3-(2,4,5-trifluorophenyl)-1H-pyrazole-5-carboxylate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-(2,4,5-Trifluorophenyl)-1H-pyrazole-3-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

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.
• Functionalization of Tripodal Scaffold Molecules on Solid Support
  作者：Cristian Guarise、Giovanni Zaupa、Leonard J. Prins、Paolo Scrimin

  DOI：10.1002/ejoc.200800259

  日期：2008.7

  A versatile synthetic approach is described for the functionalization of tripodal scaffold molecules on solid support. Intrinsic problems related to the attachment of tripodal scaffolds to a resin (for example mono- vs. polyadducts and intramolecular cyclizations) are studied and solutions are provided. The synthetic approach relies on the use of specific protecting groups in the critical steps of

  描述了一种用于在固体支持物上对三足支架分子进行功能化的通用合成方法。研究了与将三脚架支架连接到树脂（例如单加合物与多加合物和分子内环化）相关的内在问题并提供了解决方案。合成方法依赖于在合成的关键步骤中使用特定的保护基团。然而，重要的是，支架分子上的保护基团从未使用过，这显着促进了支架变异，例如在组合研究中。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)