5-(4-amidinophenyl)-2-furancarboxylic acid | 779316-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(4-amidinophenyl)-2-furancarboxylic acid
• 英文别名: 5-(4-carbamimidoylphenyl)furan-2-carboxylic acid
• CAS: 779316-86-8
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: UGGIFZIECOFCPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100.31
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  四亚甲基二胺 、 5-(4-amidinophenyl)-2-furancarboxylic acid 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 1,4-bis[[5-(4-amidinophenyl)furyl]-2-carboxamido]butane
  参考文献：
  名称：

  Aromatic Extended Bisamidines: Synthesis, Inhibition of Topoisomerases, and Anticancer Cytotoxicity in Vitro

  摘要：

  A series of four aromatic extended bisamidines (12-15) differing in the nature of their terminal basic side chains were synthesized and evaluated for cytotoxic activity in MCF-7 cultured breast cancer cells. The concentrations of 12, 13, 14, and 15 needed to inhibit [H-3]thymidine incorporation Into DNA by 50% (IC50) were found to be 53 muM, 85 muM, 77 muM, and 97 muM, respectively. To test whether cytotoxic properties were related to DNA-binding and topoisomerase action, the bisamidines 12-15 were evaluated in a cell-free system. Data from the ethidium displacement assay showed that bisamidines 12-15 have significant affinity for DNA and show moderate specificity for AT base pairs. In the topoisomerase II assay, the relaxation of DNA was inhibited with all four drugs and the extent of inhibition was directly proportional to the drug concentration. This suggests that DNA binding may be implicated in the cytotoxicity of these bisamidines, possibly by inhibiting interactions between topoisomerase II and their DNA targets.

  DOI：

  10.1002/1521-4184(200107)334:7<235::aid-ardp235>3.0.co;2-#
• 作为产物：
  描述：

  对氨基苯腈 在 盐酸 、 lithium hydroxide 、 氨 、 N,N'-羰基二咪唑 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 71.0h， 生成 5-(4-amidinophenyl)-2-furancarboxylic acid
  参考文献：
  名称：

  Aromatic Extended Bisamidines: Synthesis, Inhibition of Topoisomerases, and Anticancer Cytotoxicity in Vitro

  摘要：

  A series of four aromatic extended bisamidines (12-15) differing in the nature of their terminal basic side chains were synthesized and evaluated for cytotoxic activity in MCF-7 cultured breast cancer cells. The concentrations of 12, 13, 14, and 15 needed to inhibit [H-3]thymidine incorporation Into DNA by 50% (IC50) were found to be 53 muM, 85 muM, 77 muM, and 97 muM, respectively. To test whether cytotoxic properties were related to DNA-binding and topoisomerase action, the bisamidines 12-15 were evaluated in a cell-free system. Data from the ethidium displacement assay showed that bisamidines 12-15 have significant affinity for DNA and show moderate specificity for AT base pairs. In the topoisomerase II assay, the relaxation of DNA was inhibited with all four drugs and the extent of inhibition was directly proportional to the drug concentration. This suggests that DNA binding may be implicated in the cytotoxicity of these bisamidines, possibly by inhibiting interactions between topoisomerase II and their DNA targets.

  DOI：

  10.1002/1521-4184(200107)334:7<235::aid-ardp235>3.0.co;2-#