4-N-carboxybutyl-5-fluorocytosine | 1379471-12-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-N-carboxybutyl-5-fluorocytosine
• 英文别名: 5-[(5-fluoro-2-oxo-1H-pyrimidin-6-yl)amino]pentanoic acid
• CAS: 1379471-12-1
• 化学式: C₉H₁₂FN₃O₃
• 分子量: 229.211
• InChiKey: YFROZLZDKQSHGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 5-((5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)amino)pentanoate 在 甲醇 、 potassium hydroxide 作用下， 以 水 为溶剂， 以65.4%的产率得到4-N-carboxybutyl-5-fluorocytosine
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 4-N-carboxybutyl-5-fluorocytosyl-Arg-Gln-Trp-Arg-Arg-Trp-Trp-Gln-Arg-NH2

  摘要：

  The chemical synthesis of 4-N-carboxybutyl-5-fluorocytosine (II) in solution phase starting from 5-fluorocytosine and the solid phase synthesis of Arg-Gln-Trp-Arg-Arg-Trp-Trp-Gln-Arg-NH2 attached to the 4-N-carboxybutyl-5-fluorocytosine residue at the N-terminus of the peptide (III) via peptide bond formation is reported. The target compound exhibited a significant cytotoxic activity against a culture of HepG2 cells. In addition our results demonstrated that this new compound affect cell viability, produce mitochondrial dysfunction as well as interfere with intracellular calcium homeostasis control; leading to cell malfunction and death. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.045