7-Methoxy-1-methyl-3a,4,5,9b-tetraaza-cyclopenta[a]naphthalen-3-one | 851517-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 7-Methoxy-1-methyl-3a,4,5,9b-tetraaza-cyclopenta[a]naphthalen-3-one
• 英文别名: 1-Methyl-8-methoxy-3H-pyrazolo[1,2-a]；8-methoxy-1-methylpyrazolo[1,2-a][1,2,3,4]benzotetrazin-3-one
• CAS: 851517-60-7
• 化学式: C₁₁H₁₀N₄O₂
• 分子量: 230.226
• InChiKey: JKBJSXAWCAWOHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-Methoxy-1-methyl-3a,4,5,9b-tetraaza-cyclopenta[a]naphthalen-3-one 在 水 作用下， 生成 5-Hydroxymethyl-1-(4-methoxy-phenyl)-1,2-dihydro-pyrazol-3-one
  参考文献：
  名称：

  1-Methyl-3H-pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones. Design, Synthesis, and Biological Activity of New Antitumor Agents

  摘要：

  1-Methylpyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones 4, synthesized in good to excellent yields, were designed as novel alkylating agents because of their peculiar chemical behavior. All derivatives showed antiproliferative activity against more than 50 types of tumor cell lines with GI(50) reaching sub-micromolar values. SAR studies revealed that the presence of a chlorine atom is well-tolerated in both positions 8 and 9, whereas in the case of the methyl group, switching from the 8 to the 9 position gives rise to the most active compound of the series, 4g, either for the number of cell lines inhibited and for selectivity against leukaemia and renal cancer subpanels. COMPARE and 3D-MIND computations indicate, for compounds 4, an activity profile analogous to rifamycins and cytidine analogues.

  DOI：

  10.1021/jm049075u
• 作为产物：
  描述：

  2-硝基-4-甲氧基苯胺 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 反应 3.0h， 生成 7-Methoxy-1-methyl-3a,4,5,9b-tetraaza-cyclopenta[a]naphthalen-3-one
  参考文献：
  名称：

  1-Methyl-3H-pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones. Design, Synthesis, and Biological Activity of New Antitumor Agents

  摘要：

  1-Methylpyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones 4, synthesized in good to excellent yields, were designed as novel alkylating agents because of their peculiar chemical behavior. All derivatives showed antiproliferative activity against more than 50 types of tumor cell lines with GI(50) reaching sub-micromolar values. SAR studies revealed that the presence of a chlorine atom is well-tolerated in both positions 8 and 9, whereas in the case of the methyl group, switching from the 8 to the 9 position gives rise to the most active compound of the series, 4g, either for the number of cell lines inhibited and for selectivity against leukaemia and renal cancer subpanels. COMPARE and 3D-MIND computations indicate, for compounds 4, an activity profile analogous to rifamycins and cytidine analogues.

  DOI：

  10.1021/jm049075u