6-Methoxy-4,7-dimethyl-5-nitro-1,2-dihydropyrrolo[1,2-a]indol-3-one | 155474-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-Methoxy-4,7-dimethyl-5-nitro-1,2-dihydropyrrolo[1,2-a]indol-3-one
• CAS: 155474-40-1
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: XZVVQNVBGDAHRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Methoxy-4,7-dimethyl-5-nitro-1,2-dihydropyrrolo[1,2-a]indol-3-one 在 palladium on activated charcoal 吡啶 、 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 氢气 作用下， 反应 34.0h， 生成 3-(acetyloxy)-2,3-dihydro-7-methoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indole-5,8-dione
  参考文献：
  名称：

  A Comparison of the Cytotoxic and Physical Properties of Aziridinyl Quinone Derivatives Based on the Pyrrolo[1,2-a]benzimidazole and Pyrrolo[1,2-a]indole Ring Systems

  摘要：

  The cytotoxicity and physical properties of the pyrrolo[1,2-a]benzimidazole (PBI) and pyrrolo[1,2-a]indole (PI) aziridinyl quinones were compared in order to assess the influence of the benzimidazole ring on antitumor activity and DNA reductive alkylation. Our studies show that the PI system possesses none of the cytotoxicity of the PBI systems. Unlike the PBIs, the PI system does not reductively alkylate DNA. Apparently, the benzimidazole ring favors reductive alkylation due to its electron deficient character compared to indole. in addition, the benzimidazole ring may provide the hydrogen bonding interactions required for the interaction with DNA. Our findings resulted in the elucidation of a PBI pharmacophore. Inspection of the literature revealed another drug sharing the PBI pharmacophore, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione (EO9), which remarkably has cytotoxic properties similar to those of the PBIs

  DOI：

  10.1021/jm00037a013
• 作为产物：
  描述：

  2,3-dihydro-7-methoxy-6,9-dimethyl-1H-pyrrolo<1,2-a>indol-1-one 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 以50%的产率得到6-Methoxy-4,7-dimethyl-5-nitro-1,2-dihydropyrrolo[1,2-a]indol-3-one
  参考文献：
  名称：

  A Comparison of the Cytotoxic and Physical Properties of Aziridinyl Quinone Derivatives Based on the Pyrrolo[1,2-a]benzimidazole and Pyrrolo[1,2-a]indole Ring Systems

  摘要：

  The cytotoxicity and physical properties of the pyrrolo[1,2-a]benzimidazole (PBI) and pyrrolo[1,2-a]indole (PI) aziridinyl quinones were compared in order to assess the influence of the benzimidazole ring on antitumor activity and DNA reductive alkylation. Our studies show that the PI system possesses none of the cytotoxicity of the PBI systems. Unlike the PBIs, the PI system does not reductively alkylate DNA. Apparently, the benzimidazole ring favors reductive alkylation due to its electron deficient character compared to indole. in addition, the benzimidazole ring may provide the hydrogen bonding interactions required for the interaction with DNA. Our findings resulted in the elucidation of a PBI pharmacophore. Inspection of the literature revealed another drug sharing the PBI pharmacophore, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione (EO9), which remarkably has cytotoxic properties similar to those of the PBIs

  DOI：

  10.1021/jm00037a013

文献信息

• Design of a Cyclopropyl Quinone Methide Reductive Alkylating Agent
  作者：Anlong Ouyang、Edward B. Skibo

  DOI：10.1021/jo971808d

  日期：1998.3.1

  Described herein is the formation of a cyclopropyl quinone methide species by leaving group elimination from an indole-based hydroquinone. This species is structurally related to the A-ring of CC-1065 and is a nucleophile trap. In addition, the cyclopropyl quinone methide species can trap or eliminate a proton. Unlike the A-ring of CC-1065, stereoelectronic factors favor opening of the fused cyclopropane ring so as to result in ring expansion. Also described herein is the utility of C-13 NMR spectroscopy in following the fate of the cyclopropyl quinone methide species. Finally, the cyclopropyl quinone methide species reversibly alkylates the guanine N(7) position of DNA, resulting in cytotoxicity.
• Boruah Romesh C., Skibo Edward B., J. Med. Chem, 37 (1994) N 11, S 1625-1631
  作者：Boruah Romesh C., Skibo Edward B.

  DOI：——

  日期：——
• A Comparison of the Cytotoxic and Physical Properties of Aziridinyl Quinone Derivatives Based on the Pyrrolo[1,2-a]benzimidazole and Pyrrolo[1,2-a]indole Ring Systems
  作者：Romesh C. Boruah、Edward B. Skibo

  DOI：10.1021/jm00037a013

  日期：1994.5

  The cytotoxicity and physical properties of the pyrrolo[1,2-a]benzimidazole (PBI) and pyrrolo[1,2-a]indole (PI) aziridinyl quinones were compared in order to assess the influence of the benzimidazole ring on antitumor activity and DNA reductive alkylation. Our studies show that the PI system possesses none of the cytotoxicity of the PBI systems. Unlike the PBIs, the PI system does not reductively alkylate DNA. Apparently, the benzimidazole ring favors reductive alkylation due to its electron deficient character compared to indole. in addition, the benzimidazole ring may provide the hydrogen bonding interactions required for the interaction with DNA. Our findings resulted in the elucidation of a PBI pharmacophore. Inspection of the literature revealed another drug sharing the PBI pharmacophore, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione (EO9), which remarkably has cytotoxic properties similar to those of the PBIs