Methanesulfonic acid 5,8-dihydroxy-7-methoxy-6,9-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylmethyl ester | 205177-78-2

• 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: Methanesulfonic acid 5,8-dihydroxy-7-methoxy-6,9-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylmethyl ester
• CAS: 205177-78-2
• 化学式: C₁₆H₂₁NO₆S
• 分子量: 355.412
• InChiKey: KZWHVKYDPWWLLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.99
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 5,8-dihydroxy-7-methoxy-6,9-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylmethyl ester 在 Tris-HCl buffer 、 air 、 potassium chloride 作用下， 生成 3-(hydroxymethyl)-6-methoxy-4,7-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole-5,8-dione 、 8-Hydroxy-2-methoxy-3,10-dimethyl-6,7,8,9-tetrahydropyrido[1,2-a]indole-1,4-dione 、 8-Chloro-2-methoxy-3,10-dimethyl-6,7,8,9-tetrahydropyrido[1,2-a]indole-1,4-dione 、 (6-methoxy-4,7-dimethyl-5,8-dioxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-3-yl)methyl methanesulfonate
  参考文献：
  名称：

  Design of a Cyclopropyl Quinone Methide Reductive Alkylating Agent

  摘要：

  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.

  DOI：

  10.1021/jo971808d
• 作为产物：
  描述：

  3-(hydroxymethyl)-6-methoxy-4,7-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole-5,8-dione 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.41h， 生成 Methanesulfonic acid 5,8-dihydroxy-7-methoxy-6,9-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylmethyl ester
  参考文献：
  名称：

  Design of a Cyclopropyl Quinone Methide Reductive Alkylating Agent

  摘要：

  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.

  DOI：

  10.1021/jo971808d