5-<(4-nitrophenyl)hydroxymethyl>-2,4(1H,3H)-pyrimidinedione | 102396-62-3

• 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-<(4-nitrophenyl)hydroxymethyl>-2,4(1H,3H)-pyrimidinedione
• 英文别名: 5-[hydroxy-(4-nitro-phenyl)-methyl]-1H-pyrimidine-2,4-dione；5-[hydroxy-(4-nitrophenyl)methyl]-1H-pyrimidine-2,4-dione
• CAS: 102396-62-3
• 化学式: C₁₁H₉N₃O₅
• 分子量: 263.21
• InChiKey: NBDBHDLQQIJMIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  124
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  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

文献信息

• Uracil derivatives as HIV-1 capsid protein inhibitors: design, <i>in silico</i>, <i>in vitro</i> and cytotoxicity studies
  作者：Deepthi Ramesh、Amaresh Kumar Mohanty、Anirban De、Balaji Gowrivel Vijayakumar、Aiswarya Sethumadhavan、Suresh Kumar Muthuvel、Maheswaran Mani、Tharanikkarasu Kannan

  DOI：10.1039/d2ra02450k

  日期：——

  computational studies led to the synthesis of bispyrimidine dione and tetrapyrimidine dione derivatives from uracil and aromatic aldehydes in the presence of HCl using novel methodology. The in vitro evaluation in HIV p24 assay revealed five potential uracil derivatives with IC50 values ranging from 191.5 μg ml−1 to 62.5 μg ml−1. The meta-chloro substituted uracil compound 9a showed promising activity with an IC50

  基于现有的四点药效团模型，设计了一系列新型尿嘧啶衍生物如双嘧啶二酮和四嘧啶二酮衍生物作为有效的HIV衣壳蛋白抑制剂。这些化合物最初与 HIV 衣壳蛋白单体对接，以合理化设计理念并寻找潜在的结合模式。成功的设计和计算研究导致在 HCl 存在下使用新方法从尿嘧啶和芳香醛合成双嘧啶二酮和四嘧啶二酮衍生物。HIV p24测定的体外评估揭示了五种潜在的尿嘧啶衍生物，其IC 50值范围为191.5 μg ml -1至62.5 μg ml -1。元数据-氯取代的尿嘧啶化合物9a显示出有希望的活性，IC 50值为62.5 μg ml -1，这与计算研究密切相关。正如预期的那样，所有活性化合物在 BA/F3 和 Mo7e 细胞系中均无细胞毒性，突出了周到的设计。构效关系表明位置优先和较低的log  P值是尿嘧啶化合物抑制潜力的可能原因。
• An acid-catalyzed hydroxyalkylation of uracil: a facile synthesis of 5-(arylhydroxymethyl)uracils
  作者：Bing L. Lam、Lendon N. Pridgen

  DOI：10.1021/jo00363a036

  日期：1986.6
• LAM B. L.; PRIDGEN L. N., J. ORG. CHEM., 51,(1986) N 13, 2592-2594
  作者：LAM B. L.、 PRIDGEN L. N.

  DOI：——

  日期：——
• 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.