5-[heptyloxy-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione | 1000372-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[heptyloxy-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione
• 英文别名: 5-[heptyloxy-4-(nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione；5-[heptoxy-(4-nitrophenyl)methyl]-1H-pyrimidine-2,4-dione
• CAS: 1000372-82-6
• 化学式: C₁₈H₂₃N₃O₅
• 分子量: 361.398
• InChiKey: CKLWFVCQFNUUSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 5-[heptyloxy-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 56.0h， 生成 2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl-5-[heptyloxy-(4-nitrophenyl)-methyl]-pyrimidine-2,4-dione 、 2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl-5-[heptyloxy-(4-nitrophenyl)-methyl]-pyrimidine-2,4-dione
  参考文献：
  名称：

  5- [烷氧基-（4-硝基-苯基）-甲基]-尿苷的合成及其细胞毒活性的研究

  摘要：

  合成了在5-位用5- [烷氧基-（4-硝基苯基）-甲基]部分修饰的一系列尿苷类似物。核苷以两种非对映异构体的混合物形式形成，将其分离并测试其体外针对不同癌细胞系的细胞毒性活性和抗微生物活性。研究了结构与上述活动之间的关系。在某些情况下，通过将碱基转化为核苷，细胞毒性活性略有增加。取决于烷基链的长度，注意到细胞毒性和抗微生物活性增加。核苷的细胞毒活性不是由于细胞周期改变，DNA和/或RNA合成。

  DOI：

  10.1016/j.ejmech.2010.05.003
• 作为产物：
  描述：

  5-[chloro-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione 、 正庚醇 反应 4.0h， 以72%的产率得到5-[heptyloxy-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of various 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils in their racemic form

  摘要：

  The preparation of various 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils with alkyl chain lengths C-1-C-12 is described. The synthesis is based on the preparation of 5-[chloro-(4-nitro-phenyl)-methyl]-uracil and subsequent substitution of chlorine with appropriate alcohols. The resulting ethers were tested for their cytotoxic activity in vitro against five cancer cell lines. The compounds were less active in lung resistance protein expressing cell lines, suggesting the involvement of this multidrug resistant protein in control of the biological activity. Cytotoxic substances induced rapid inhibition of DNA and modulation of RNA synthesis followed by induction of apoptosis. The data indicate that the biological activity of 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils depends on the alkyl chain length. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.022

文献信息

• Synthesis and cytotoxic activity of various 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils in their racemic form
  作者：Lucie Spáčilová、Petr Džubák、Marián Hajdúch、Soňa Křupková、Pavel Hradil、Jan Hlaváč

  DOI：10.1016/j.bmcl.2007.09.022

  日期：2007.12

  The preparation of various 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils with alkyl chain lengths C-1-C-12 is described. The synthesis is based on the preparation of 5-[chloro-(4-nitro-phenyl)-methyl]-uracil and subsequent substitution of chlorine with appropriate alcohols. The resulting ethers were tested for their cytotoxic activity in vitro against five cancer cell lines. The compounds were less active in lung resistance protein expressing cell lines, suggesting the involvement of this multidrug resistant protein in control of the biological activity. Cytotoxic substances induced rapid inhibition of DNA and modulation of RNA synthesis followed by induction of apoptosis. The data indicate that the biological activity of 5-[alkoxy-(4-nitro-phenyl)-methyl]-uracils depends on the alkyl chain length. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of 5-[alkoxy-(4-nitro-phenyl)-methyl]-uridines and study of their cytotoxic activity
  作者：Lucie Brulíková、Petr Džubák、Marián Hajdúch、Lenka Lachnitová、Madhusudhan Kollareddy、Milan Kolář、Kateřina Bogdanová、Jan Hlaváč

  DOI：10.1016/j.ejmech.2010.05.003

  日期：2010.9

  the 5-[alkoxy-(4-nitrophenyl)-methyl] moiety was synthesized. Nucleosides were formed as a mixture of two diastereoisomers, which were separated and tested for their cytotoxic activity in vitro against different cancer cell lines and for antimicrobial activity. Relationships between structure and the above mentioned activities were studied. The cytotoxic activity was slightly increased in some cases

  合成了在5-位用5- [烷氧基-（4-硝基苯基）-甲基]部分修饰的一系列尿苷类似物。核苷以两种非对映异构体的混合物形式形成，将其分离并测试其体外针对不同癌细胞系的细胞毒性活性和抗微生物活性。研究了结构与上述活动之间的关系。在某些情况下，通过将碱基转化为核苷，细胞毒性活性略有增加。取决于烷基链的长度，注意到细胞毒性和抗微生物活性增加。核苷的细胞毒活性不是由于细胞周期改变，DNA和/或RNA合成。