1,3-dicarbamyl-2,5-dimethoxybenzene | 479065-62-8

• 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: 1,3-dicarbamyl-2,5-dimethoxybenzene
• 英文别名: 2,5-Dimethoxybenzene-1,3-dicarboxamide
• CAS: 479065-62-8
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: VGNGUYJSNPHGRV-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C
• 沸点：
  342.6±42.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dicarbamyl-2,5-dimethoxybenzene 在 氯化亚砜 、 硫酸 、 三乙胺 作用下， 反应 5.58h， 生成 2,5-dimethoxyisophthalic acid methyl ester
  参考文献：
  名称：

  Pyrimidoquinazoline-Based Antitumor Agents. Design of Topoisomerase II to DNA Cross-linkers with Activity against Protein Kinases

  摘要：

  A series of pyrimidoquinazoline analogues, possessing either 4,5-g or 5,4-g fusion, were studied with respect to cytotoxicity, topoisomerase II inhibitory activity, in vivo activity, and DNA cleavage and DNA-protein cross-linking properties. These analogues were designed as electron-deficient anthraquinones with dual alkylating centers to cross-link DNA with topoisomerase II. Our studies verified the presence of DNA-protein cross-linking in vitro as well as topoisomerase II poisoning by pyrimidoquinazoline analogues. In addition, COMPARE analysis revealed that the pyrimidoquinazolines possess inhibitory activity against both topoisomerase II and protein kinases, such as the paullones, a dual property observed in other antineoplastic agents influencing phosphoester transfer.

  DOI：

  10.1021/jm020285l
• 作为产物：
  描述：

  2,5-Dimethoxy-1,3-benzoldicarbonitril 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以64%的产率得到1,3-dicarbamyl-2,5-dimethoxybenzene
  参考文献：
  名称：

  Pyrimidoquinazoline-Based Antitumor Agents. Design of Topoisomerase II to DNA Cross-linkers with Activity against Protein Kinases

  摘要：

  A series of pyrimidoquinazoline analogues, possessing either 4,5-g or 5,4-g fusion, were studied with respect to cytotoxicity, topoisomerase II inhibitory activity, in vivo activity, and DNA cleavage and DNA-protein cross-linking properties. These analogues were designed as electron-deficient anthraquinones with dual alkylating centers to cross-link DNA with topoisomerase II. Our studies verified the presence of DNA-protein cross-linking in vitro as well as topoisomerase II poisoning by pyrimidoquinazoline analogues. In addition, COMPARE analysis revealed that the pyrimidoquinazolines possess inhibitory activity against both topoisomerase II and protein kinases, such as the paullones, a dual property observed in other antineoplastic agents influencing phosphoester transfer.

  DOI：

  10.1021/jm020285l

文献信息

• Pyrimidoquinazoline-Based Antitumor Agents. Design of Topoisomerase II to DNA Cross-linkers with Activity against Protein Kinases
  作者：Edward B. Skibo、Xiaofen Huang、Rogelio Martinez、Robert H. Lemus、William A. Craigo、Robert T. Dorr

  DOI：10.1021/jm020285l

  日期：2002.12.1

  A series of pyrimidoquinazoline analogues, possessing either 4,5-g or 5,4-g fusion, were studied with respect to cytotoxicity, topoisomerase II inhibitory activity, in vivo activity, and DNA cleavage and DNA-protein cross-linking properties. These analogues were designed as electron-deficient anthraquinones with dual alkylating centers to cross-link DNA with topoisomerase II. Our studies verified the presence of DNA-protein cross-linking in vitro as well as topoisomerase II poisoning by pyrimidoquinazoline analogues. In addition, COMPARE analysis revealed that the pyrimidoquinazolines possess inhibitory activity against both topoisomerase II and protein kinases, such as the paullones, a dual property observed in other antineoplastic agents influencing phosphoester transfer.