4-(1H-indole-3-yl)-1H-imidazo[4,5-c]pyridine-2-amine | 1201171-46-1

• 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: 4-(1H-indole-3-yl)-1H-imidazo[4,5-c]pyridine-2-amine
• 英文别名: 4-(1H-indol-3-yl)-1H-imidazo[4,5-c]pyridin-2-amine
• CAS: 1201171-46-1
• 化学式: C₁₄H₁₁N₅
• 分子量: 249.275
• InChiKey: VDQPKRPHLSTBEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1H-indole-3-yl)-1H-imidazo[4,5-c]pyridine-2-amine 、 三氟乙酸 以 乙腈 为溶剂， 生成 4-(1H-indole-3-yl)-1H-imidazo[4,5-c]pyridine-2-amine trifluoroacetate
  参考文献：
  名称：

  A One-Pot Synthesis and Biological Activity of Ageladine A and Analogues

  摘要：

  A one-pot synthesis of ageladine A and analogues is reported. The key Pictet - Spengler reaction between 2-aminohistamine and aryl aldehydes has been successfully utilized for the synthesis of the natural product and 14 analogues. These compounds were screened for their matrix metalloprotease (MMP) and kinase inhibition to develop the first structure-activity relationship of ageladine A analogues. One compound, which showed significant kinase activity but little MMP inhibitory activity, was found to be highly active in an antiangiogenic screen, suggesting that the angiogenic activity of ageladine A is not associated with MMP inhibition but rather kinase inhibitory activity. Cytotoxicity was excluded as a mode of action by the assay of ageladine A and an analogue against 60 human cell lines.

  DOI：

  10.1021/jm200039m
• 作为产物：
  描述：

  tert-butyl 3-(2-amino-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-4-yl)-1H-indole-1-carboxylate 在 四氯苯醌 、 氨 作用下， 以 氯仿 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以71%的产率得到4-(1H-indole-3-yl)-1H-imidazo[4,5-c]pyridine-2-amine
  参考文献：
  名称：

  [EN] SYNTHESIS OF AGELADINE A AND ANALOGS THEREOF
  [FR] SYNTHÈSE D'AGÉLADINE A ET D'ANALOGUES DE CELLE-CI

  摘要：

  该发明描述了一种一锅法合成结构式(I)化合物或其同分异构体的过程。将结构式(II)化合物或其同分异构体与RdCHO结构的醛缩合形成缩合产物。然后将所得缩合产物在同一反应混合物中氧化，以产生结构式(I)化合物或其同分异构体。

  公开号：

  WO2009152584A1

文献信息

• SYNTHESIS OF AGELADINE A AND ANALOGS THEREOF
  申请人：Karuso Peter Helmuth

  公开号：US20110152313A1

  公开（公告）日：2011-06-23

  The invention describes a one pot process for synthesizing a compound of structure (I), or a tautomer thereof. A compound of structure (II), or a tautomer thereof, and an aldehyde of structure R d CHO are condensed to form a condensation product. The resulting condensation product is then oxidized in the same reaction mixture to produce the compound of structure (I) or a tautomer thereof.

  该发明描述了一种单锅反应合成化合物(I)或其互变异构体的过程。化合物(II)或其互变异构体与结构为RdCHO的醛缩合形成缩合产物。随后，在相同的反应混合物中氧化所得的缩合产物，以产生化合物(I)或其互变异构体。
• [EN] SYNTHESIS OF AGELADINE A AND ANALOGS THEREOF<br/>[FR] SYNTHÈSE D'AGÉLADINE A ET D'ANALOGUES DE CELLE-CI
  申请人：UNIV MACQUARIE

  公开号：WO2009152584A1

  公开（公告）日：2009-12-23

  The invention describes a one pot process for synthesizing a compound of structure (I), or a tautomer thereof. A compound of structure (II), or a tautomer thereof, and an aldehyde of structure RdCHO are condensed to form a condensation product. The resulting condensation product is then oxidized in the same reaction mixture to produce the compound of structure (I) or a tautomer thereof.

  该发明描述了一种一锅法合成结构式(I)化合物或其同分异构体的过程。将结构式(II)化合物或其同分异构体与RdCHO结构的醛缩合形成缩合产物。然后将所得缩合产物在同一反应混合物中氧化，以产生结构式(I)化合物或其同分异构体。
• A One-Pot Synthesis and Biological Activity of Ageladine A and Analogues
  作者：Sudhir R. Shengule、Wendy L. Loa-Kum-Cheung、Christopher R. Parish、Mélina Blairvacq、Laurent Meijer、Yoichi Nakao、Peter Karuso

  DOI：10.1021/jm200039m

  日期：2011.4.14

  A one-pot synthesis of ageladine A and analogues is reported. The key Pictet - Spengler reaction between 2-aminohistamine and aryl aldehydes has been successfully utilized for the synthesis of the natural product and 14 analogues. These compounds were screened for their matrix metalloprotease (MMP) and kinase inhibition to develop the first structure-activity relationship of ageladine A analogues. One compound, which showed significant kinase activity but little MMP inhibitory activity, was found to be highly active in an antiangiogenic screen, suggesting that the angiogenic activity of ageladine A is not associated with MMP inhibition but rather kinase inhibitory activity. Cytotoxicity was excluded as a mode of action by the assay of ageladine A and an analogue against 60 human cell lines.