N-(4'-acetyl-3',5,6-trimethoxybiphenyl-3-yl)-N'-{4-[2-(dimethylamino)ethoxy]-2-methylphenyl}urea | 1454615-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4'-acetyl-3',5,6-trimethoxybiphenyl-3-yl)-N'-{4-[2-(dimethylamino)ethoxy]-2-methylphenyl}urea
• 英文别名: 1-[3-(4-Acetyl-3-methoxyphenyl)-4,5-dimethoxyphenyl]-3-[4-[2-(dimethylamino)ethoxy]-2-methylphenyl]urea
• CAS: 1454615-36-1
• 化学式: C₂₉H₃₅N₃O₆
• 分子量: 521.613
• InChiKey: QCIAAKLJZYOWPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.36
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(4'-acetyl-3',5,6-trimethoxybiphenyl-3-yl)-N'-{4-[2-(dimethylamino)ethoxy]-2-methylphenyl}urea 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以0.38 g的产率得到N-{4-[2-(dimethylamino)ethoxy]-2-methylphenyl}-N'-{4'-[(1E)-N-hydroxylethanimidoyl]-3',5,6-trimethoxybiphenyl-3-yl}urea
  参考文献：
  名称：

  Biphenyl derivatives incorporating urea unit as novel VEGFR-2 inhibitors: Design, synthesis and biological evaluation

  摘要：

  A series of novel biphenyl urea derivates were synthesized and investigated for their potential to inhibit vascular endothelial growth factor receptor-2 (VEGFR-2). In particular, A7, B3 and B4 displayed significant enzymatic inhibitory activities, with IC50 values of 4.06, 4.55 and 5.26 nM. Compound A7 exhibited potent antiproliferative activity on several cell lines. SAR study suggested that the introduction of methyl at ortho-position of the biphenyl urea and tertiary amine moiety could improve VEGFR-2 inhibitory activity and antitumor effects. Molecular docking indicated that the urea moiety formed four hydrogen bonds with DFG residue. These biphenyl ureas could serve as promising lead compounds for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.027
• 作为产物：
  描述：

  4-溴-2-羟基苯乙酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 6.16h， 生成 N-(4'-acetyl-3',5,6-trimethoxybiphenyl-3-yl)-N'-{4-[2-(dimethylamino)ethoxy]-2-methylphenyl}urea
  参考文献：
  名称：

  Biphenyl derivatives incorporating urea unit as novel VEGFR-2 inhibitors: Design, synthesis and biological evaluation

  摘要：

  A series of novel biphenyl urea derivates were synthesized and investigated for their potential to inhibit vascular endothelial growth factor receptor-2 (VEGFR-2). In particular, A7, B3 and B4 displayed significant enzymatic inhibitory activities, with IC50 values of 4.06, 4.55 and 5.26 nM. Compound A7 exhibited potent antiproliferative activity on several cell lines. SAR study suggested that the introduction of methyl at ortho-position of the biphenyl urea and tertiary amine moiety could improve VEGFR-2 inhibitory activity and antitumor effects. Molecular docking indicated that the urea moiety formed four hydrogen bonds with DFG residue. These biphenyl ureas could serve as promising lead compounds for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.027