5-fluoro-2-(1H-pyrazol-1-yl)pyridine | 1259030-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-fluoro-2-(1H-pyrazol-1-yl)pyridine
• 英文别名: 1-(5-fluoropyrid-2-yl)-1H-pyrazole；5-Fluoro-2-(1-pyrazolyl)pyridine；5-fluoro-2-pyrazol-1-ylpyridine
• CAS: 1259030-32-4
• 化学式: C₈H₆FN₃
• 分子量: 163.154
• InChiKey: CZZCITRSDGFSKS-UHFFFAOYSA-N

物化性质

• 沸点：
  244.1±25.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-(1H-pyrazol-1-yl)pyridine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 溴 、 potassium acetate 、 caesium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-[1-(5-fluoropyridin-2-yl)pyrazol-4-yl]-N-(1-methylpiperidin-4-yl)imidazo[1,2-b]pyridazin-6-amine
  参考文献：
  名称：

  Imidazopyridazines as potent inhibitors of Plasmodium falciparum calcium-dependent protein kinase 1 (PfCDPK1): Preparation and evaluation of pyrazole linked analogues

  摘要：

  The structural diversity and SAR in a series of imidazopyridazine inhibitors of Plasmodium falciparum calcium dependent protein kinase 1 (PfCDPK1) has been explored and extended. The opportunity to further improve key ADME parameters by means of lowering log D was identified, and this was achieved by replacement of a six-membered (hetero)aromatic linker with a pyrazole. A short SAR study has delivered key examples with useful in vitro activity and ADME profiles, good selectivity against a human kinase panel and improved levels of lipophilic ligand efficiency. These new analogues thus provide a credible additional route to further development of the series. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.010
• 作为产物：
  描述：

  吡唑 、 2-溴-5-氟吡啶 在 copper(l) iodide 、 L-脯氨酸 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 5-fluoro-2-(1H-pyrazol-1-yl)pyridine
  参考文献：
  名称：

  [EN] UREA SUBSTITUTED SULPHONAMIDE DERIVATIVES
  [FR] DERIVES DE SULFONAMIDE SUBSTITUES PAR UREE

  摘要：

  本发明涉及含有脲基的磺胺类衍生物。该发明还涉及将这些衍生物用作胶原受体整合素的抑制剂，特别是α2β1整合素抑制剂，例如在涉及表达胶原受体的细胞和血小板的疾病和医疗状况中使用，其用作药物，例如用于治疗血栓形成、炎症、癌症和血管疾病，含有它们的药物组合物以及制备它们的方法。这些磺胺类衍生物具有一般式(I)或(I')。

  公开号：

  WO2010146236A1

文献信息

• Copper-Catalyzed C–N Bond Exchange of N-Heterocyclic Substituents around Pyridine and Pyrimidine Cores
  作者：Sheng Tao、Enhui Ji、Lei Shi、Ning Liu、Liang Xu、Bin Dai

  DOI：10.1055/s-0036-1590893

  日期：2017.12

  copper-catalyzed transfer N-heteroarylation strategy using a C–N bond exchange reaction is described. This reaction accommodates a wide range of pyridine and pyrimidine rings bearing halogen atoms, which have wide utility for subsequent transformations. This method provides a direct and operationally simple approach for modifying complex molecules by the exchange of N-heterocyclic substituents. A copper-catalyzed

  S. Tao和E. Ji的贡献相等。 抽象的 描述了使用C–N键交换反应的铜催化转移N-杂芳基化策略。该反应可容纳范围广泛的带有卤素原子的吡啶和嘧啶环，它们对于随后的转化具有广泛的用途。该方法提供了直接且操作简单的方法，用于通过交换N杂环取代基来修饰复杂分子。 描述了使用C–N键交换反应的铜催化转移N-杂芳基化策略。该反应可容纳范围广泛的带有卤素原子的吡啶和嘧啶环，它们对于随后的转化具有广泛的用途。该方法提供了直接且操作简单的方法，用于通过交换N杂环取代基来修饰复杂分子。
• UREA SUBSTITUTED SULPHONAMIDE DERIVATIVES
  申请人：Koivunen Jarkko Tapani

  公开号：US20120196884A1

  公开（公告）日：2012-08-02

  The present invention relates to sulphonamide derivatives, whith a urea moiety. The invention also relates to the use of the derivatives as inhibitors of collagen receptor integrins, especially α2β1 integrin inhibitors e.g. in connection with diseases and medical conditions that involve the action of cells and platelets expressing collagen receptors, their use as a medicament, e.g. for the treatment of thrombosis, inflammation, cancer and vascular diseases, pharmaceutical compositions containing them and a process for preparing them. The sulphonamide derivatives have the general formula (I) or (I′).

  本发明涉及含有尿素基团的磺酰胺衍生物。本发明还涉及将这些衍生物用作胶原受体整合素的抑制剂，特别是α2β1整合素抑制剂，例如在涉及表达胶原受体的细胞和血小板的疾病和医疗状况中，将其用作药物，例如用于治疗血栓形成、炎症、癌症和血管疾病，包含它们的制药组合物以及制备它们的过程。磺酰胺衍生物具有通式（I）或（I′）。
• [EN] UREA SUBSTITUTED SULPHONAMIDE DERIVATIVES<br/>[FR] DERIVES DE SULFONAMIDE SUBSTITUES PAR UREE
  申请人：BIOTIE THERAPIES CORP

  公开号：WO2010146236A1

  公开（公告）日：2010-12-23

  The present invention relates to sulphonamide derivatives, whith a urea moiety. The invention also relates to the use of the derivatives as inhibitors of collagen receptor integrins, especially α2β1 integrin inhibitors e.g. in connection with diseases and medical conditions that involve the action of cells and platelets expressing collagen receptors, their use as a medicament, e.g. for the treatment of thrombosis, inflammation, cancer and vascular diseases, pharmaceutical compositions containing them and a process for preparing them. The sulphonamide derivatives have the general formula (I) or (I').

  本发明涉及含有脲基的磺胺类衍生物。该发明还涉及将这些衍生物用作胶原受体整合素的抑制剂，特别是α2β1整合素抑制剂，例如在涉及表达胶原受体的细胞和血小板的疾病和医疗状况中使用，其用作药物，例如用于治疗血栓形成、炎症、癌症和血管疾病，含有它们的药物组合物以及制备它们的方法。这些磺胺类衍生物具有一般式(I)或(I')。
• Imidazopyridazines as potent inhibitors of Plasmodium falciparum calcium-dependent protein kinase 1 (PfCDPK1): Preparation and evaluation of pyrazole linked analogues
  作者：Jonathan M. Large、Simon A. Osborne、Ela Smiljanic-Hurley、Keith H. Ansell、Hayley M. Jones、Debra L. Taylor、Barbara Clough、Judith L. Green、Anthony A. Holder

  DOI：10.1016/j.bmcl.2013.08.010

  日期：2013.11

  The structural diversity and SAR in a series of imidazopyridazine inhibitors of Plasmodium falciparum calcium dependent protein kinase 1 (PfCDPK1) has been explored and extended. The opportunity to further improve key ADME parameters by means of lowering log D was identified, and this was achieved by replacement of a six-membered (hetero)aromatic linker with a pyrazole. A short SAR study has delivered key examples with useful in vitro activity and ADME profiles, good selectivity against a human kinase panel and improved levels of lipophilic ligand efficiency. These new analogues thus provide a credible additional route to further development of the series. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.