methyl (4aS,12aS)-7-[[3-[(4aS,12aS)-4a-ethyl-1-hydroxy-6-methoxycarbonyl-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridin-7-yl]-1,2,3,4-tetrahydroquinolin-2-yl]methyl]-4a-ethyl-1-hydroxy-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridine-6-carboxylate

• 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: methyl (4aS,12aS)-7-[[3-[(4aS,12aS)-4a-ethyl-1-hydroxy-6-methoxycarbonyl-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridin-7-yl]-1,2,3,4-tetrahydroquinolin-2-yl]methyl]-4a-ethyl-1-hydroxy-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridine-6-carboxylate
• 化学式: C₄₈H₅₃N₅O₆
• 分子量: 795.979
• InChiKey: MXWZJSPRWTVYGV-CZQBIAOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  59
• 可旋转键数：
  9
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (4aS,12aS)-7-[[3-[(4aS,12aS)-4a-ethyl-1-hydroxy-6-methoxycarbonyl-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridin-7-yl]-1,2,3,4-tetrahydroquinolin-2-yl]methyl]-4a-ethyl-1-hydroxy-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridine-6-carboxylate 在 titanium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以38%的产率得到methyl (4aS,12aR)-7-[[3-[(4aS,12aR)-4a-ethyl-6-methoxycarbonyl-2,3,4,12a-tetrahydro-1H-indolo[1,2-a][1,8]naphthyridin-7-yl]-1,2,3,4-tetrahydroquinolin-2-yl]methyl]-4a-ethyl-2,3,4,12a-tetrahydro-1H-indolo[1,2-a][1,8]naphthyridine-6-carboxylate
  参考文献：
  名称：

  Access to New Cytotoxic Bisindole Alkaloids by a Modified Borch Reductive Amination Process

  摘要：

  A slight modification of the Borch reductive amination method (delayed addition of NaBH3CN) was applied to an indole aldehyde compound, analog of the natural alkaloid, goniomitine. This reaction led to a series of new cytotoxic bisindole alkaloids with a 1,2,3,4-tetrahydroquinoline bridge.

  DOI：

  10.3987/com-00-9001
• 作为产物：
  描述：

  aniline hydrochloride 、 methyl (4aS,12aS)-4a-ethyl-1-hydroxy-7-(2-oxoethyl)-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridine-6-carboxylate 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以45%的产率得到methyl (4aS,12aS)-7-[[3-[(4aS,12aS)-4a-ethyl-1-hydroxy-6-methoxycarbonyl-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridin-7-yl]-1,2,3,4-tetrahydroquinolin-2-yl]methyl]-4a-ethyl-1-hydroxy-2,3,4,12a-tetrahydroindolo[1,2-a][1,8]naphthyridine-6-carboxylate
  参考文献：
  名称：

  一系列新型的细胞毒性双吲哚生物碱的合成。

  摘要：

  通过与各种苯胺的还原胺化反应合成具有1,2,3,4-四氢喹啉桥的原始细胞毒性双吲哚生物碱。最具细胞毒性的化合物显示出高剂量依赖性的细胞周期效应，并在G1期积累。指出了起始苯胺的取代对反应和所产生的二聚体的细胞毒性的影响。

  DOI：

  10.1016/s0960-894x(00)00600-4

文献信息

• Synthesis of a novel series of cytotoxic bisindole alkaloids
  作者：Marion Raoul、Corinne Schaeffer、Stéphane Léonce、Alain Pierré、Ghanem Atassi、Reynald Hocquemiller、Guy Lewin

  DOI：10.1016/s0960-894x(00)00600-4

  日期：2001.1

  Original cytotoxic bisindole alkaloids with a 1,2,3,4-tetrahydroquinoline bridge were synthesized by reductive amination with various anilines. The most cytotoxic compounds display a high and dose-dependent cell cycle effect with accumulation in the G1 phase. Influence of substitution of the starting aniline on the reaction and on cytotoxicity of produced dimers was pointed out.

  通过与各种苯胺的还原胺化反应合成具有1,2,3,4-四氢喹啉桥的原始细胞毒性双吲哚生物碱。最具细胞毒性的化合物显示出高剂量依赖性的细胞周期效应，并在G1期积累。指出了起始苯胺的取代对反应和所产生的二聚体的细胞毒性的影响。
• Access to New Cytotoxic Bisindole Alkaloids by a Modified Borch Reductive Amination Process
  作者：Guy Lewin、Corinne Schaeffer、Reynald Hocquemiller、Edgar Jacoby、Stéphane Léonce、Alain Pierré、Ghanem Atassi

  DOI：10.3987/com-00-9001

  日期：——

  A slight modification of the Borch reductive amination method (delayed addition of NaBH3CN) was applied to an indole aldehyde compound, analog of the natural alkaloid, goniomitine. This reaction led to a series of new cytotoxic bisindole alkaloids with a 1,2,3,4-tetrahydroquinoline bridge.