3-(3-amino-9H-pyrido[3,4-b]indol-9-yl)-N-(2-aminoethyl)propanamide | 220472-67-3

• 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: 3-(3-amino-9H-pyrido[3,4-b]indol-9-yl)-N-(2-aminoethyl)propanamide
• 英文别名: 3-amino-9-N-(2-aminoethyl)carbamoylethyl-β-carboline；N-(2-aminoethyl)-3-(3-aminopyrido[3,4-b]indol-9-yl)propanamide
• CAS: 220472-67-3
• 化学式: C₁₆H₁₉N₅O
• 分子量: 297.36
• InChiKey: MEVRTECIUVBIDH-UHFFFAOYSA-N

物化性质

• 熔点：
  178-178.5 °C
• 沸点：
  579.2±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl N-nitroso-N-methylcarbamate 、 3-(3-amino-9H-pyrido[3,4-b]indol-9-yl)-N-(2-aminoethyl)propanamide 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以79%的产率得到3-(3-amino-9H-pyrido[3,4-b]indol-9-yl)-N-(2-(3-methyl-3-nitrosoureido)ethyl)propanamide
  参考文献：
  名称：

  A novel macroreticular-type fluorous polystyrene resin and its application to the synthesis of a 3-amino-β-carboline derivative with N-methyl-N-nitrosourea conjugation via fluorous solid-phase reaction: a comparative study of fluorous solid-, solid-, and liquid-phase reactions

  摘要：

  A novel fluorous polystyrene (FPS) MR-resin was applied to a fluorous solid-phase (FSP) reaction. The MR-FPS resin actually was developed previously and possessed excellent chemical resistance to acids and alkalis, and a fluorous-tagged compound was homogeneously and loosely immobilized on the resin. The synthesis of an antitumor drug, an N-methyl-N-nirosourea conjugated 3-amino-beta-carboline derivative, was accomplished with a high yield by using this new fluorous reaction system. Using only filtration, the fluorous 3-amino-beta-carboline derivatives immobilized on the MR-FPS resin were easily recovered from the reaction mixtures. As an extention of this approach, a diversity synthesis of 3-amino-9-benzyl-beta-carboline derivatives was applied to the FSP method giving high yields. Finally, the FSP synthesis was compared with the corresponding conventional solid- and liquid-phase methods of synthesis. The FSP reaction was superior in terms of the reactivity of the substrate and the ease of product separation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.072
• 作为产物：
  描述：

  9-(2-cyanoethyl)pyrido[3,4-b]indole-3-carbohydrazide 在 盐酸 、 水 、 sulfur 、 溶剂黄146 、 sodium nitrite 作用下， 反应 3.0h， 生成 3-(3-amino-9H-pyrido[3,4-b]indol-9-yl)-N-(2-aminoethyl)propanamide
  参考文献：
  名称：

  Synthesis of b-Carboline Derivatives and Their Interaction with Duplex-DNA

  摘要：

  DOI：

  10.3987/com-98-8330