5-[chloro-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione | 1000372-64-4

• 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-[chloro-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione
• 英文别名: 5-[chloro-(4-nitrophenyl)methyl]-1H-pyrimidine-2,4-dione
• CAS: 1000372-64-4
• 化学式: C₁₁H₈ClN₃O₄
• 分子量: 281.655
• InChiKey: YLVUSOQKARCPSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[chloro-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione 在 水 作用下， 反应 2.0h， 以98%的产率得到5-<(4-nitrophenyl)hydroxymethyl>-2,4(1H,3H)-pyrimidinedione
  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
• 作为产物：
  描述：

  对硝基苯甲醛 、 尿嘧啶 在 盐酸 作用下， 反应 4.0h， 以68%的产率得到5-[chloro-(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.