6-Amino-2-[(4-nitrophenyl)methyl]benzo[de]isoquinoline-1,3-dione | 186299-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-Amino-2-[(4-nitrophenyl)methyl]benzo[de]isoquinoline-1,3-dione
• CAS: 186299-08-1
• 化学式: C₁₉H₁₃N₃O₄
• 分子量: 347.33
• InChiKey: IGUFBGWRUVYHNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 6-Amino-2-[(4-nitrophenyl)methyl]benzo[de]isoquinoline-1,3-dione 以 吡啶 为溶剂， 以86%的产率得到N-[2-(4-Nitro-benzyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl]-butyramide
  参考文献：
  名称：

  Naphthalimido derivatives as antifolate thymidylate synthase inhibitors

  摘要：

  A new series of N-(substituted)benzyl-1,8-naphthalimides 4, structurally related to the previously reported thymidylate synthase (TS) inhibitor naphthaleins 3, were synthesized and compounds tested for their inhibition of several species of TS. Moreover, their in vitro cytotoxicity together with antimycotic and antibacterial properties were assayed. While no activity was detected in the antibacterial tests, the m-nitro (4ae) and the p-nitro (4af) derivatives were found able to partially inhibit TS at low micromolar concentrations. Introduction of nitro or (substituted)-amino groups in position 4 of the naphthalic ring always led to less active compounds.

  DOI：

  10.1016/s0223-5234(97)86180-6
• 作为产物：
  描述：

  4-氨基-1,8-萘胺 、 1-(氯甲基)-4-硝基苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以91%的产率得到6-Amino-2-[(4-nitrophenyl)methyl]benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Naphthalimido derivatives as antifolate thymidylate synthase inhibitors

  摘要：

  A new series of N-(substituted)benzyl-1,8-naphthalimides 4, structurally related to the previously reported thymidylate synthase (TS) inhibitor naphthaleins 3, were synthesized and compounds tested for their inhibition of several species of TS. Moreover, their in vitro cytotoxicity together with antimycotic and antibacterial properties were assayed. While no activity was detected in the antibacterial tests, the m-nitro (4ae) and the p-nitro (4af) derivatives were found able to partially inhibit TS at low micromolar concentrations. Introduction of nitro or (substituted)-amino groups in position 4 of the naphthalic ring always led to less active compounds.

  DOI：

  10.1016/s0223-5234(97)86180-6