1,3-dioctylthymine | 869006-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-dioctylthymine
• 英文别名: 5-Methyl-1,3-dioctylpyrimidine-2,4-dione
• CAS: 869006-25-7
• 化学式: C₂₁H₃₈N₂O₂
• 分子量: 350.545
• InChiKey: DEPXTBUASVAFFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dioctylthymine 在 2,6-二甲基吡啶 、 dipotassium peroxodisulfate 、 硫酸 、 copper(II) sulfate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以60%的产率得到5-formyl-1,3-dioctyluracil
  参考文献：
  名称：

  wittig烯化合成5-取代的尿嘧啶和2,4-二甲氧基嘧啶

  摘要：

  高纯度的各种新的5-烯基尿嘧啶是通过将稳定化的5-甲酰基-1-辛基-尿嘧啶，5-甲酰基-1,3-二辛基尿嘧啶和5-甲酰基-2,4-二甲氧基嘧啶进行Wittig烯化反应而制得的。半稳定的磷化氢。基于1 H NMR光谱数据讨论产物的构象。

  DOI：

  10.1002/jhet.5570420615
• 作为产物：
  描述：

  1-溴辛烷 、 胸腺嘧啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以50%的产率得到1,3-dioctylthymine
  参考文献：
  名称：

  wittig烯化合成5-取代的尿嘧啶和2,4-二甲氧基嘧啶

  摘要：

  高纯度的各种新的5-烯基尿嘧啶是通过将稳定化的5-甲酰基-1-辛基-尿嘧啶，5-甲酰基-1,3-二辛基尿嘧啶和5-甲酰基-2,4-二甲氧基嘧啶进行Wittig烯化反应而制得的。半稳定的磷化氢。基于1 H NMR光谱数据讨论产物的构象。

  DOI：

  10.1002/jhet.5570420615

文献信息

• C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells
  作者：Eleonora Brognara、Ilaria Lampronti、Giulia Breveglieri、Alessandro Accetta、Roberto Corradini、Alex Manicardi、Monica Borgatti、Alessandro Canella、Chiara Multineddu、Rosangela Marchelli、Roberto Gambari

  DOI：10.1016/j.ejphar.2011.09.024

  日期：2011.12

  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.
• Synthesis of 5-substituted uracils and 2,4-dimethoxypyrimidines by wittig olefination
  作者：Evdoxia Coutouli-Argyropoulou、Christina Zachariadou

  DOI：10.1002/jhet.5570420615

  日期：2005.9

  A variety of new 5-alkenyluracils has been prepared in high yields by Wittig olefination of 5-formyl-1-octy-luracil, 5-formyl-1,3-dioctyluracil and 5-formyl-2,4-dimethoxy pyrimidine with stabilized and semistabi-lized phosphorus ylides. The conformation of the products is discussed on the basis of 1H NMR spectral data.

  高纯度的各种新的5-烯基尿嘧啶是通过将稳定化的5-甲酰基-1-辛基-尿嘧啶，5-甲酰基-1,3-二辛基尿嘧啶和5-甲酰基-2,4-二甲氧基嘧啶进行Wittig烯化反应而制得的。半稳定的磷化氢。基于1 H NMR光谱数据讨论产物的构象。