N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzamide | 1425335-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzamide
• 英文别名: n-(2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzamide；N-[2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzamide
• CAS: 1425335-63-2
• 化学式: C₁₉H₂₃BN₂O₄
• 分子量: 354.214
• InChiKey: QAZWXZDTIXPKRL-UHFFFAOYSA-N

物化性质

• 沸点：
  426.7±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzamide 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 N-(5-(2-(cyclopropylamino)pyrimidin-4-yl)-2-methoxypyridin-3-yl)benzamide
  参考文献：
  名称：

  Synthesis and profiling of a 3-aminopyridin-2-one-based kinase targeted fragment library: Identification of 3-amino-5-(pyridin-4-yl)pyridin-2(1H)-one scaffold for monopolar spindle 1 (MPS1) and Aurora kinases inhibition

  摘要：

  Screening a 3-aminopyridin-2-one based fragment library against a 26-kinase panel representative of the human kinome identified 3-amino 5 (1-methyl-1H-pyrazol-4-yl)pyridin-2(1H)-one (2) and 3-amino-5(pyridin-4-yl)pyridin-2(1H)-one (3) as ligand efficient inhibitors of the mitotic kinase Monopolar Spindle 1 (MPS1) and the Aurora kinase family. These kinases are well recognised as attractive targets for therapeutic intervention for treating cancer. Elucidation of the binding mode of these fragments and their analogues has been carried out by X-ray crystallography. Structural studies have identified key interactions with a conserved lysine residue and have highlighted potential regions of MPS1 which could be targeted to improve activity and selectivity. (C) 2018 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2018.04.033
• 作为产物：
  描述：

  3-氨基-5-溴-2-甲氧基吡啶 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 28.68h， 生成 N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzamide
  参考文献：
  名称：

  一种咪唑并吡啶类衍生物及其制备方法和应用

  摘要：

  本发明涉及药物化合物技术领域，具体公开一种咪唑并吡啶类衍生物及其制备方法和应用。本发明以咪唑并吡啶作为骨架，在骨架上通过引入取代芳香基团和甲基哌嗪、哌啶等基团，设计得到了一系列新型结构的咪唑并吡啶类衍生物。其中，引入的特定的芳香基团，可增强化合物与PI3K相关受体的P‑Π或Π‑Π相互作用，增强化合物对PI3K信号通路的抑制，从而提高抗肿瘤活性；引入的甲基哌嗪基团，可增加化合物与受体的氢键结合力，提高生物相容性和抗肿瘤活性。本发明提供的新型结构的咪唑并吡啶类衍生物具有优良的抗肿瘤活性，为新型抗肿瘤药物的开发提供了新的药物化合物，丰富了咪唑并吡啶化合物的数据库，潜在应用价值较高。

  公开号：

  CN117964621A

文献信息

• Synthesis and profiling of a 3-aminopyridin-2-one-based kinase targeted fragment library: Identification of 3-amino-5-(pyridin-4-yl)pyridin-2(1H)-one scaffold for monopolar spindle 1 (MPS1) and Aurora kinases inhibition
  作者：Daren Fearon、Isaac M. Westwood、Rob L.M. van Montfort、Richard Bayliss、Keith Jones、Vassilios Bavetsias

  DOI：10.1016/j.bmc.2018.04.033

  日期：2018.7

  Screening a 3-aminopyridin-2-one based fragment library against a 26-kinase panel representative of the human kinome identified 3-amino 5 (1-methyl-1H-pyrazol-4-yl)pyridin-2(1H)-one (2) and 3-amino-5(pyridin-4-yl)pyridin-2(1H)-one (3) as ligand efficient inhibitors of the mitotic kinase Monopolar Spindle 1 (MPS1) and the Aurora kinase family. These kinases are well recognised as attractive targets for therapeutic intervention for treating cancer. Elucidation of the binding mode of these fragments and their analogues has been carried out by X-ray crystallography. Structural studies have identified key interactions with a conserved lysine residue and have highlighted potential regions of MPS1 which could be targeted to improve activity and selectivity. (C) 2018 The Authors. Published by Elsevier Ltd.