1-phenacyluracil | 130278-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenacyluracil
• 英文别名: 1-(2-Oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione；1-phenacylpyrimidine-2,4-dione
• CAS: 130278-38-5
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: OMGJBMXWULADKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenacyluracil 、 苯肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 1-(2-phenyl-2-(2-phenylhydrazineylidene)ethyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Structure–cytotoxicity relationship of a novel series of miconazole-like compounds

  摘要：

  In the current study, two novel classes of the carboacyclic nucleosides having miconazole-like scaffolds as imidazole- and pyrimidine-based compounds were examined for their cytotoxic properties. The aim was to establish a relation between cytotoxic activity and nature of the synthetic compounds. While Escherichia coli (DH5 alpha) and human erythromyeloblastoid leukemia cell line (K562) were the target cells, depending on the type of substitution made, ranges of antibacterial and antineoplastic activities were observed. Also the electron-donating and electron-accepting properties of the ligands were proved to play a crucial role in their cytotoxic activities. Accordingly, the substitutions associated with the marked improvement of cytotoxic activities can be considered as the significant point in construction of new generation of either antibacterial or antineoplastic agents.

  DOI：

  10.1007/s00044-011-9716-z
• 作为产物：
  描述：

  2-溴苯乙酮 、 尿嘧啶 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 1-phenacyluracil
  参考文献：
  名称：

  一些新型腙无环核苷类似物的合成。

  摘要：

  描述了类似于咪康唑支架的新型腙无环核苷的合成。在这一系列无环核苷中，嘧啶以及嘌呤和其他唑类衍生物取代了咪康唑中的咪唑功能，并且使用苯肼将醚基团替换为腙部分。为了解释 (E)-腙衍生物而不是 (Z)-异构体的主要形成，进行了 PM3 半经验量子力学计算，表明 (E)-异构体具有较低的形成热。

  DOI：

  10.3762/bjoc.6.49

文献信息

• A Facile Synthesis of 1-Monosubstituted and Unsymmetrically 1,3-Disubstituted Uracils
  作者：Harjit Singh、Pawan Aggarwal、Subodh Kumar

  DOI：10.1055/s-1990-26926

  日期：——

  Heating of 2,4-bis(trimethylsiloxy)pyrimidine with functionalised alkyl halides in 1,2-dichloroethane in the presence of iodine affords exclusively 1-substituted uracils, which can be benzylated at N-3 with benzyl chloride under phase-transfer catalysis.

  在碘存在下，将 2,4-双（三甲基硅氧基）嘧啶与官能化烷基卤化物在 1,2 二氯乙烷中加热，可得到完全由 1 取代的尿嘧啶，在相转移催化下，尿嘧啶的 N-3 可与氯化苄发生苄基化反应。
• Hedayatullah, Mir; Roger, Annie, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1093 - 1096
  作者：Hedayatullah, Mir、Roger, Annie

  DOI：——

  日期：——
• LAB. MICROCOMPUT., 9,(1990) N, C. 520-522
  作者：

  DOI：——

  日期：——
• Synthesis of some novel hydrazono acyclic nucleoside analogues
  作者：Mohammad N Soltani Rad、Ali Khalafi-Nezhad、Somayeh Behrouz

  DOI：10.3762/bjoc.6.49

  日期：——

  The syntheses of novel hydrazono acyclic nucleosides similar to miconazole scaffolds are described. In this series of acyclic nucleosides, pyrimidine as well as purine and other azole derivatives replaced the imidazole function in miconazole and the ether group was replaced with a hydrazone moiety using phenylhydrazine. To interpret the dominant formation of (E)-hydrazone derivatives rather than (Z)-isomers

  描述了类似于咪康唑支架的新型腙无环核苷的合成。在这一系列无环核苷中，嘧啶以及嘌呤和其他唑类衍生物取代了咪康唑中的咪唑功能，并且使用苯肼将醚基团替换为腙部分。为了解释 (E)-腙衍生物而不是 (Z)-异构体的主要形成，进行了 PM3 半经验量子力学计算，表明 (E)-异构体具有较低的形成热。
• Structure–cytotoxicity relationship of a novel series of miconazole-like compounds
  作者：Reza Yousefi、Ali Khalafi-Nezhad、Mohammad Navid Soltani Rad、Somayeh Behrouz、Farhad Panahi、Mansoore Esmaili、Sayed Mahmoud Ghaffari、Ali Niazi、Ali Akbar Moosavi-Movahedi

  DOI：10.1007/s00044-011-9716-z

  日期：2012.8

  In the current study, two novel classes of the carboacyclic nucleosides having miconazole-like scaffolds as imidazole- and pyrimidine-based compounds were examined for their cytotoxic properties. The aim was to establish a relation between cytotoxic activity and nature of the synthetic compounds. While Escherichia coli (DH5 alpha) and human erythromyeloblastoid leukemia cell line (K562) were the target cells, depending on the type of substitution made, ranges of antibacterial and antineoplastic activities were observed. Also the electron-donating and electron-accepting properties of the ligands were proved to play a crucial role in their cytotoxic activities. Accordingly, the substitutions associated with the marked improvement of cytotoxic activities can be considered as the significant point in construction of new generation of either antibacterial or antineoplastic agents.