3-(4-fluorophenyl)-3-oxo-2-(pyrimidin-4-yl)propanenitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-fluorophenyl)-3-oxo-2-(pyrimidin-4-yl)propanenitrile
• 英文别名: 3-(4-Fluorophenyl)-3-oxo-2-pyrimidin-4-ylpropanenitrile
• 化学式: C₁₃H₈FN₃O
• 分子量: 241.224
• InChiKey: TYRBNVFSCNKPSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-3-oxo-2-(pyrimidin-4-yl)propanenitrile 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  An Efficient and Practical Method for the Synthesis of the 5-Acylamino-4-(4-pyrimidinyl)isoxazole Derivative AKP-001, a Potent P38 MAP Kinase Inhibitor

  摘要：

  5-Acylamino-4-(4-pyrimidinyl)isoxazole derivative AKP-001 is a p38 mitogen-activated protein kinase inhibitor previously developed in our laboratory as an anti-inflammatory agent. Herein, we report our studies leading to the development of an improved synthetic route to AKP-001, which shows several advantages compared to the previously reported laboratory-scale process, namely, a lower number of steps, superior chemical yield and atom efficiency, and applicability at an industrial scale.

  DOI：

  10.3987/com-17-13700
• 作为产物：
  描述：

  4-甲基嘧啶 在 盐酸羟胺 、 sodium amide 、 六甲基二硅氮烷 、 sodium hydroxide 作用下， 以 甲醇 、 二乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-(4-fluorophenyl)-3-oxo-2-(pyrimidin-4-yl)propanenitrile
  参考文献：
  名称：

  An Efficient and Practical Method for the Synthesis of the 5-Acylamino-4-(4-pyrimidinyl)isoxazole Derivative AKP-001, a Potent P38 MAP Kinase Inhibitor

  摘要：

  5-Acylamino-4-(4-pyrimidinyl)isoxazole derivative AKP-001 is a p38 mitogen-activated protein kinase inhibitor previously developed in our laboratory as an anti-inflammatory agent. Herein, we report our studies leading to the development of an improved synthetic route to AKP-001, which shows several advantages compared to the previously reported laboratory-scale process, namely, a lower number of steps, superior chemical yield and atom efficiency, and applicability at an industrial scale.

  DOI：

  10.3987/com-17-13700

文献信息

• Condensed pyrazole derivatives with interleukin-1 and tumour necrosis factor inhibitory activity
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0531901A2

  公开（公告）日：1993-03-17

  1. A compound of the formula : wherein R¹ isaryl which may have suitable substituent(s) or heterocyclic group which may have suitable substituent(s), R² isaryl which may have suitable substituent(s) or heterocyclic group which may have suitable substituent(s), and Y isa bivalent radical selected from (in which ---- means single bond or double bond), each of which may have suitable substituent(s), and pharmaceutically acceptable salts thereof, processes for their preparation and pharmaceutical compositions comprising them.

  1.式中的化合物： 式中 R¹为芳基，可具有合适的取代基，或为杂环基，可具有合适的取代基、 R² 是芳基，可带有合适的取代基或杂环基，可带有合适的取代基，以及 Y 是二价基，选自 (其中 ---- 指单键或双键），其中每个基团可具有合适的取代基，以及 它们的药学上可接受的盐、其制备工艺和包含它们的药物组合物。
• US5356897A
  申请人：——

  公开号：US5356897A

  公开（公告）日：1994-10-18
• US5478827A
  申请人：——

  公开号：US5478827A

  公开（公告）日：1995-12-26
• US5624931A
  申请人：——

  公开号：US5624931A

  公开（公告）日：1997-04-29
• An Efficient and Practical Method for the Synthesis of the 5-Acylamino-4-(4-pyrimidinyl)isoxazole Derivative AKP-001, a Potent P38 MAP Kinase Inhibitor
  作者：Shuji Ohta、Takahisa Saito、Jun-ya Kato、Shuichiro Sato、Hiroyuki Hayashi、Koichi Hasumi

  DOI：10.3987/com-17-13700

  日期：——

  5-Acylamino-4-(4-pyrimidinyl)isoxazole derivative AKP-001 is a p38 mitogen-activated protein kinase inhibitor previously developed in our laboratory as an anti-inflammatory agent. Herein, we report our studies leading to the development of an improved synthetic route to AKP-001, which shows several advantages compared to the previously reported laboratory-scale process, namely, a lower number of steps, superior chemical yield and atom efficiency, and applicability at an industrial scale.