2-chloro-N-(3-chlorophenyl)-5-nitropyrimidin-4-amine

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-chloro-N-(3-chlorophenyl)-5-nitropyrimidin-4-amine
• 化学式: C₁₀H₆Cl₂N₄O₂
• 分子量: 285.089
• InChiKey: KEYAXYKXGBFDMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4-(4-aminobenzamido)-2,2,6,6-tetramethylpiperidin-1-yl]oxidanyl 、 2-chloro-N-(3-chlorophenyl)-5-nitropyrimidin-4-amine 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以68%的产率得到4-((4-((3-chlorophenyl)amino)-5-nitropyrimidin-2-yl)amino)-N-(2,2,6,6-tetramethyl-1-oxyl)benzamide
  参考文献：
  名称：

  Synthesis and identification of 2,4-bisanilinopyrimidines bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential Aurora A inhibitors

  摘要：

  The Aurora kinases are a family of serine/threonine kinases that interact with components of the mitotic apparatus and serve as potential therapeutic targets in oncology. Herein, we reported a series of 2,4-bisanilinopyrimidines bearing 2,2,6,6-tetramethylpiperidine-N-oxyl with selective inhibition of Aurora A in either enzymatic assays or cellular phenotypic assays, and displaying more potent anti-proliferation compared with that of VX-680. The most potent compound 10a forms better interaction with Aurora A than Aurora B in molecular docking. Mechanistic studies revealed that 10a disrupt the spindle formation, block the cell cycle progression in the G2/M phase and induce apoptosis in HeLa cell. These results suggested that the produced series of compounds are potential anticancer agents for further development as selective Aurora A inhibitors.

  DOI：

  10.1016/j.bmc.2018.11.006
• 作为产物：
  描述：

  3-氯苯胺 、 2,4-二氯-5 硝基嘧啶 以 二氯甲烷 为溶剂， 反应 12.0h， 以68%的产率得到2-chloro-N-(3-chlorophenyl)-5-nitropyrimidin-4-amine
  参考文献：
  名称：

  Synthesis and identification of 2,4-bisanilinopyrimidines bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential Aurora A inhibitors

  摘要：

  The Aurora kinases are a family of serine/threonine kinases that interact with components of the mitotic apparatus and serve as potential therapeutic targets in oncology. Herein, we reported a series of 2,4-bisanilinopyrimidines bearing 2,2,6,6-tetramethylpiperidine-N-oxyl with selective inhibition of Aurora A in either enzymatic assays or cellular phenotypic assays, and displaying more potent anti-proliferation compared with that of VX-680. The most potent compound 10a forms better interaction with Aurora A than Aurora B in molecular docking. Mechanistic studies revealed that 10a disrupt the spindle formation, block the cell cycle progression in the G2/M phase and induce apoptosis in HeLa cell. These results suggested that the produced series of compounds are potential anticancer agents for further development as selective Aurora A inhibitors.

  DOI：

  10.1016/j.bmc.2018.11.006

文献信息

• Synthesis and identification of 2,4-bisanilinopyrimidines bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential Aurora A inhibitors
  作者：Chun-Yan Sang、Wen-Wen Qin、Xiu-Juan Zhang、Yu Xu、You-Zhen Ma、Xing-Rong Wang、Ling Hui、Shi-Wu Chen

  DOI：10.1016/j.bmc.2018.11.006

  日期：2019.1

  The Aurora kinases are a family of serine/threonine kinases that interact with components of the mitotic apparatus and serve as potential therapeutic targets in oncology. Herein, we reported a series of 2,4-bisanilinopyrimidines bearing 2,2,6,6-tetramethylpiperidine-N-oxyl with selective inhibition of Aurora A in either enzymatic assays or cellular phenotypic assays, and displaying more potent anti-proliferation compared with that of VX-680. The most potent compound 10a forms better interaction with Aurora A than Aurora B in molecular docking. Mechanistic studies revealed that 10a disrupt the spindle formation, block the cell cycle progression in the G2/M phase and induce apoptosis in HeLa cell. These results suggested that the produced series of compounds are potential anticancer agents for further development as selective Aurora A inhibitors.