methyl 1-(3-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate | 1207608-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 1-(3-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate
• CAS: 1207608-28-3
• 化学式: C₁₅H₁₁N₃O₄
• 分子量: 297.27
• InChiKey: XIKMLRKDJQIWBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.26
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 1-(3-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到methyl 1-(3-aminophenyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of pyrrolo[3,2-b]pyridine derivatives against melanoma

  摘要：

  Synthesis of a new series of diarylureas and amides having pyrrolo[3,2-b]pyridine scaffold is described. Their in vitro antiproliferative activity against human melanoma cell line A375 and HS 27 human fibroblast cell line was tested and the effect of substituents on the pyrrolo[3,2-b]pyridine was investigated. The newly synthesized compounds, except meta-substituted derivatives (Ij-k and Iv-w), generally showed superior or similar activity against A375 to Sorafenib. Among all of these derivatives, compounds Ir and It having 5-benzylamide substituted 4'-amide moieties showed the most potent antiproliferative activity against A375. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.08.005
• 作为产物：
  描述：

  1H-吡咯并[3,2-B]吡啶-5-羧酸甲酯 、 1-碘-3-硝基苯 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 以66%的产率得到methyl 1-(3-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of pyrrolo[3,2-b]pyridine derivatives against melanoma

  摘要：

  Synthesis of a new series of diarylureas and amides having pyrrolo[3,2-b]pyridine scaffold is described. Their in vitro antiproliferative activity against human melanoma cell line A375 and HS 27 human fibroblast cell line was tested and the effect of substituents on the pyrrolo[3,2-b]pyridine was investigated. The newly synthesized compounds, except meta-substituted derivatives (Ij-k and Iv-w), generally showed superior or similar activity against A375 to Sorafenib. Among all of these derivatives, compounds Ir and It having 5-benzylamide substituted 4'-amide moieties showed the most potent antiproliferative activity against A375. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.08.005