ethyl [5-(N-(2-naphthylcarboxyl)aminomethyl)uracil-1-yl]acetate | 1392205-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl [5-(N-(2-naphthylcarboxyl)aminomethyl)uracil-1-yl]acetate
• CAS: 1392205-58-1
• 化学式: C₂₀H₁₉N₃O₅
• 分子量: 381.388
• InChiKey: NKPXJLFXACQCAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110.26
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  ethyl (5-azidomehtyluracil-1-yl)acetate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl [5-(N-(2-naphthylcarboxyl)aminomethyl)uracil-1-yl]acetate
  参考文献：
  名称：

  C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells

  摘要：

  The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2011.09.024