2-Methyl-4-(2-pyrrolidin-1-ylethoxy)aniline | 1181364-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Methyl-4-(2-pyrrolidin-1-ylethoxy)aniline
• CAS: 1181364-80-6
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: JDUSDTHONNYTIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三光气 、 1-(5'-amino-2',3,3'-trimethoxybiphenyl-4-yl)ethanone 、 2-Methyl-4-(2-pyrrolidin-1-ylethoxy)aniline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 以45%的产率得到N-(4'-acetyl-3',5,6-trimethoxybiphenyl-3-yl)-N'-[2-methyl-4-(2-pyrrolidin-1-ylethoxy)phenyl]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

文献信息

• Biphenyl derivatives incorporating urea unit as novel VEGFR-2 inhibitors: Design, synthesis and biological evaluation
  作者：Chen Wang、Hongping Gao、Jinyun Dong、Yanmin Zhang、Ping Su、Yaling Shi、Jie Zhang

  DOI：10.1016/j.bmc.2013.11.027

  日期：2014.1

  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.