(Z)-N-(2-methyl-4-nitrophenyl)but-2-enamide

• 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: (Z)-N-(2-methyl-4-nitrophenyl)but-2-enamide
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: MTLUGHXVCAAHEJ-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-N-(2-methyl-4-nitrophenyl)but-2-enamide 在 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (Z)-1-(4-(3-amino-6-methylisoxazolo[3,4-b]pyridin-4-yl)phenyl)-3-(4-but-2-enamido-3-methylphenyl)urea
  参考文献：
  名称：

  Design, synthesis and structure-activity relationship of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure as multi-target inhibitors against receptor tyrosine kinase

  摘要：

  Inspired by that the multi-target inhibitors against receptor tyrosine kinases (RTKs) have significantly improved the effect of clinical treatment for cancer, and based on the chemical structure of Linifanib (ABT-869, Abbott), two series of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure were designed and synthesized as multi-target inhibitors against RTKs. The preliminary biological evaluation showed that several compounds exhibited comparable potency with Linifanib. Compound S21 was identified as the most potent inhibitor against Fms-like tyrosine kinase 3 (FLT-3), kinase insert domain containing receptor (KDR) and platelet-derived growth factor receptor beta (PDGFR-beta) with its IC50 values were 4 nM, 3 nM and 8 nM respectively, it also showed potent inhibitory activities against several cancer cells.

  DOI：

  10.1016/j.bmc.2018.08.013
• 作为产物：
  描述：

  巴豆酰氯 、 4-硝基-2-甲苯胺 在 N,N-二异丙基乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以93%的产率得到(Z)-N-(2-methyl-4-nitrophenyl)but-2-enamide
  参考文献：
  名称：

  Design, synthesis and structure-activity relationship of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure as multi-target inhibitors against receptor tyrosine kinase

  摘要：

  Inspired by that the multi-target inhibitors against receptor tyrosine kinases (RTKs) have significantly improved the effect of clinical treatment for cancer, and based on the chemical structure of Linifanib (ABT-869, Abbott), two series of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure were designed and synthesized as multi-target inhibitors against RTKs. The preliminary biological evaluation showed that several compounds exhibited comparable potency with Linifanib. Compound S21 was identified as the most potent inhibitor against Fms-like tyrosine kinase 3 (FLT-3), kinase insert domain containing receptor (KDR) and platelet-derived growth factor receptor beta (PDGFR-beta) with its IC50 values were 4 nM, 3 nM and 8 nM respectively, it also showed potent inhibitory activities against several cancer cells.

  DOI：

  10.1016/j.bmc.2018.08.013

文献信息

• Design, synthesis and structure-activity relationship of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure as multi-target inhibitors against receptor tyrosine kinase
  作者：Zhi-Hao Shi、Feng-Tao Liu、Hao-Zhong Tian、Yan-Min Zhang、Nian-Guang Li、Tao Lu

  DOI：10.1016/j.bmc.2018.08.013

  日期：2018.9

  Inspired by that the multi-target inhibitors against receptor tyrosine kinases (RTKs) have significantly improved the effect of clinical treatment for cancer, and based on the chemical structure of Linifanib (ABT-869, Abbott), two series of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure were designed and synthesized as multi-target inhibitors against RTKs. The preliminary biological evaluation showed that several compounds exhibited comparable potency with Linifanib. Compound S21 was identified as the most potent inhibitor against Fms-like tyrosine kinase 3 (FLT-3), kinase insert domain containing receptor (KDR) and platelet-derived growth factor receptor beta (PDGFR-beta) with its IC50 values were 4 nM, 3 nM and 8 nM respectively, it also showed potent inhibitory activities against several cancer cells.