3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione | 137596-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione
• CAS: 137596-53-3
• 化学式: C₂₃H₂₄N₄O₃
• 分子量: 404.469
• InChiKey: CGYSWSODGZYDPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.08
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3,7,8,10-四甲基-苯并[g]蝶啶-2,4(3H,10H)-二酮 、 1-amino-2-phenylbut-3-en-2-ol 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  设计单胺氧化酶灭活剂的新策略。叔烯丙基和炔丙基氨基醇的探索性研究

  摘要：

  提出了一种设计单胺氧化酶 (MAO) 抑制剂的新策略。该策略基于这样的前提，即通过活性位点亲核试剂的烷基化操作的含有叔胺的 MAO 灭活剂通过单电子转移 (SET) 原位激活到 MAO-黄素辅因子，形成胺阳离子自由基，然后进行二次断裂反应产生反应性亲电试剂。当前工作的目的是评估该提案在设计新的 MAO 灭活剂系列方面的可行性和适用性。根据已记录的 β-氨基-醇阳离子自由基的逆醇醛型断裂反应性，预计叔 β-烯丙基和-炔丙基 β-氨基-醇可作为 SET 促进过程中共轭酮的前体。支持这一假设的证据是从该氨基醇家族成员与 3-甲基荧光素 (3MLF) 的模型 SET 光反应研究中获得的。4a-和4a,5-黄素的高效生产...

  DOI：

  10.1021/ja973978d

文献信息

• SET photochemistry of flavin-cyclopropylamine systems. Models for proposed monoamine oxidase inhibition mechanisms
  作者：Jong Man Kim、Michael A. Bogdan、Patrick S. Mariano

  DOI：10.1021/ja00024a034

  日期：1991.11

  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.