1-(2-hydroxyquinolin-4-yl)-3-(prop-2-yn-1-yl)urea | 1373331-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2-hydroxyquinolin-4-yl)-3-(prop-2-yn-1-yl)urea
• CAS: 1373331-87-3
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: QJTRDLIVRRYCSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.25
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-羟基喹啉-4-羧酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 1-(2-hydroxyquinolin-4-yl)-3-(prop-2-yn-1-yl)urea
  参考文献：
  名称：

  Synthesis and evaluation of 1-(substituted)-3-prop-2-ynylureas as antiangiogenic agents

  摘要：

  Novel urea derivatives of alkynes have been designed, synthesized, and evaluated as potential cancer therapeutics leads. The most active 1-((3-chloromethyl)phenyl)-3-prop-2-ynylurea (1) exhibited cytotoxic effect against HELA and MCF-7 cell lines with IC50 values of 1.55 mu M and 1.48 mu M, respectively. Further investigation on tube formation assay in human vein umbilical cells (HUVEC) demonstrated that 1 and methyl 4-(3-(3-ethynylureido)benzyloxy) benzoate (6) possess antiangiogenic activity, with minimum effective dose of 25 nM (for 1) and 6.25 mu M (for 6). The ED50 of 1 and 6 were found to be 0.26 mu M and 17.52 mu M, respectively. The results from in vitro tyrosine kinase assay indicated the EGFR inhibition of 1 over other kinases (VEGFR2, FGFR1 and PDGFR beta). The cytotoxicity of 1 against EGFR over-expressing cell line A431 (IC50 36 nM) was comparable to that of erlotinib. The binding mode of 1 from docking simulation in the EGFR active site revealed that the urea motif formed hydrogen bonding with Lys745, Thr854 and Asp855 in hydrophobic pocket of EGFR. Compound 1 is considered as a potential lead for further optimization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.029