1-amino-5,8,10,11-tetramethyl-1-phenyl-2,3-dihydro-1H-benzo[g]pyrrolo[2,1-e]pteridine-4,6(5H,8H)-dione | 137596-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-amino-5,8,10,11-tetramethyl-1-phenyl-2,3-dihydro-1H-benzo[g]pyrrolo[2,1-e]pteridine-4,6(5H,8H)-dione
• CAS: 137596-55-5
• 化学式: C₂₃H₂₅N₅O₂
• 分子量: 403.484
• InChiKey: JNRILHFBMJAUBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82.24
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-苯基环丙胺 、 3,7,8,10-四甲基-苯并[g]蝶啶-2,4(3H,10H)-二酮 以 甲醇 为溶剂， 反应 0.17h， 生成 1-amino-5,8,10,11-tetramethyl-1-phenyl-2,3-dihydro-1H-benzo[g]pyrrolo[2,1-e]pteridine-4,6(5H,8H)-dione
  参考文献：
  名称：

  SET photochemistry of flavin-cyclopropylamine systems. Models for proposed monoamine oxidase inhibition mechanisms

  摘要：

  Single electron transfer (SET) induced photochemical reactions of 3-methyllumiflavin (3-MLF) with the cyclo-propylamines, trans-2-phenylcyclopropylamine (1) and 1-phenylcyclopropylamine (4), have been explored with the aim of defining the nature of and mechanisms for the reaction pathways followed, The excited-state SET processes probed in this investigation were designed to model those proposed previously for inactivation of the flavine-containing enzyme, monoamine oxidase, by these same cyclopropylamines. Irradiation of 3-MLF in an N2-purged solution containing cyclopropylamine 4 leads to generation of the C-4a,N-5-propanodihydroflavin 14 as the major primary photoproduct. This substance, which is formed by an SET-promoted radical coupling mechanism, is transformed to the C-4a-(benzoylethyl)dihydroflavin 6 under hydrolytic conditions. Several other minor, cyclopropylamine-derived products are also generated in this reaction, again via radical pathways. In contrast, irradiation of an air-saturated solution of 3-MLF and 4 produces the epoxy ketone 8 efficiently. In this reaction, 3-MLF serves as an SET photosensitizer for the oxidative ring-opening reaction that converts 4 to 8. Finally, the C-4a,N-5-propanodihydroflavin adducts 17 and 18 are generated along with substances arising by secondary reaction of a primary product, cinnamaldehyde (20), when 3-MLF is irradiated in an N2-purged solution containing the cyclopropylamine 1. Mechanistic aspects of these bona ride SET flavin-cyclopropylamine reactions and their possible relationship to proposals made earlier about the nature of and mechanisms for monoamine oxidase inactivation by the same cyclopropylamines are discussed.

  DOI：

  10.1021/ja00024a034