(2S,6S)-2,6-Dimethyl-7-oxo-6-{2-[(quinoxaline-2-carbonyl)-amino]-ethoxy}-1,4-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester | 544481-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (2S,6S)-2,6-Dimethyl-7-oxo-6-{2-[(quinoxaline-2-carbonyl)-amino]-ethoxy}-1,4-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,6S)-2,6-dimethyl-7-oxo-6-[2-(quinoxaline-2-carbonylamino)ethoxy]-1,4-diazabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 544481-15-4
• 化学式: C₂₀H₂₃N₅O₅
• 分子量: 413.433
• InChiKey: QPGMGFGZWZRZMR-RFFXKOPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,6S)-2,6-Dimethyl-7-oxo-6-{2-[(quinoxaline-2-carbonyl)-amino]-ethoxy}-1,4-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (4E,11E)-(2S,6S,9S,13S)-2,6,9,13-Tetramethyl-7,14-dioxo-6,13-bis-{2-[(quinoxaline-2-carbonyl)-amino]-ethoxy}-1,4,8,11-tetraaza-cyclotetradeca-4,11-diene-2,9-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of 5,12-Dioxocyclam Nickel (II) Complexes Having Quinoxaline Substituents at the 6 and 13 Positions as Potential DNA Bis-Intercalating and Cleaving Agents

  摘要：

  Several dioxocyclams containing quinoxaline moieties, as well as their nickel(II) complexes were synthesized and studied for their ability to bind and oxidatively cleave DNA. Although no evidence for binding by intercalation was found, the ability of the Ni(II) complexes to cleave DNA in the presence of Oxone was strongly dependent on both the nature and the spatial orientation of the quinoxaline moieties, suggesting at least transient association of these complexes with DNA.

  DOI：

  10.1021/jo020708r
• 作为产物：
  描述：

  (S)-N-(benzyloxycarbonyl)-4-methyl-4-carbomethoxy-Δ²-imidazoline 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 20.0~70.0 ℃ 、551.58 kPa 条件下， 反应 4.0h， 生成 (2S,6S)-2,6-Dimethyl-7-oxo-6-{2-[(quinoxaline-2-carbonyl)-amino]-ethoxy}-1,4-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 5,12-Dioxocyclam Nickel (II) Complexes Having Quinoxaline Substituents at the 6 and 13 Positions as Potential DNA Bis-Intercalating and Cleaving Agents

  摘要：

  Several dioxocyclams containing quinoxaline moieties, as well as their nickel(II) complexes were synthesized and studied for their ability to bind and oxidatively cleave DNA. Although no evidence for binding by intercalation was found, the ability of the Ni(II) complexes to cleave DNA in the presence of Oxone was strongly dependent on both the nature and the spatial orientation of the quinoxaline moieties, suggesting at least transient association of these complexes with DNA.

  DOI：

  10.1021/jo020708r