4-(pyridine-2-yl)-1H-imidazo [4,5-c] pyridine-2-amine | 1201171-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(pyridine-2-yl)-1H-imidazo [4,5-c] pyridine-2-amine
• 英文别名: 4-(pyridine-2-yl)-1H-imidazo[4,5-c]pyridin-2-amine；4-(pyridin-2-yl)-1H-imidazo[4,5-c]pyridin-2-amine；4-(pyrid-2-yl)-1H-imidazo[4,5-c]pyridin-2-amine；4-pyridin-2-yl-1H-imidazo[4,5-c]pyridin-2-amine
• CAS: 1201171-41-6
• 化学式: C₁₁H₉N₅
• 分子量: 211.226
• InChiKey: JZRNXAPRPJTGOG-UHFFFAOYSA-N

物化性质

• 沸点：
  523.9±58.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(pyridine-2-yl)-1H-imidazo [4,5-c] pyridine-2-amine 、 三氟乙酸 以 乙腈 为溶剂， 生成 4-(pyridine-2-yl)-1H-imidazo[4,5-c]pyridin-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：

  4-(pyridine-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-amine 在 palladium 10% on activated carbon 作用下， 以 乙醇 为溶剂， 以87%的产率得到4-(pyridine-2-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

• One-Pot Evolution of Ageladine A through a Bio-Inspired Cascade towards Selective Modulators of Neuronal Differentiation
  作者：Takayuki Iwata、Satoshi Otsuka、Kazuki Tsubokura、Almira Kurbangalieva、Daisuke Arai、Koichi Fukase、Yoichi Nakao、Katsunori Tanaka

  DOI：10.1002/chem.201602651

  日期：2016.10.4

  A bio‐inspired cascade reaction has been developed for the construction of the marine natural product ageladine A and a de novo array of its N1‐substituted derivatives. This cascade features a 2‐aminoimidazole formation that is modeled after an arginine post‐translational modification and an aza‐electrocyclization. It can be effectively carried out in a one‐pot procedure from simple anilines or guanidines

  已开发出一种受生物启发的级联反应，用于构建海洋天然产物ageladine A及其从头开始的N1取代衍生物阵列。该级联具有2-氨基咪唑的形成，该结构是在精氨酸的翻译后修饰和氮杂-电环化之后建模的。它可以通过简单的苯胺或胍的一锅法有效地进行，从而导致原本无法通过合成获得的法拉定A的结构类似物。我们发现该结构新颖的文库中的某些化合物在调节神经分化方面显示出显着的活性。即，这些化合物选择性地激活或抑制神经干细胞向神经元的分化，而向星形胶质细胞的分化可忽略不计。
• イミダゾピリジンアミン化合物、その製造方法及び用途
  申请人：中尾 洋一

  公开号：JP2016079181A

  公开（公告）日：2016-05-16

  【課題】優れた神経細胞分化促進作用を有し、安全性の高い従来にないイミダゾピリジンアミン化合物又はその薬学的に許容可能な塩若しくは溶媒和物、その用途、及びその製造方法の提供。【解決手段】式１で表されるイミダゾピリジンアミン化合物、その薬学的に許容可能な塩若しくは溶媒和物を含有する医薬組成物、及び神経細胞分化促進剤。［Ｒ１〜Ｒ３及びＸは各々独立に、Ｈ、ハロゲン等；Ｒ１及びＲ２又はＲ１及びＲ３は、Ｎ原子と一緒になって、非置換／置換の５〜８員の複素環を形成してもよい；ｍは０〜２の整数、Ａ環は置換／非置換の炭素環又はヘテロ環］【選択図】図１

  提供具有优良神经细胞分化促进作用且具有高安全性的非传统咪唑吡啶胺化合物或其药学上可接受的盐或溶剂络合物，其用途以及其制备方法。在式1中表示的咪唑吡啶胺化合物，其药学上可接受的盐或溶剂络合物的医药组合物，以及神经细胞分化促进剂。[R1〜R3和X分别独立地是H、卤素等；R1和R2或R1和R3可以与N原子结合形成未取代/取代的5〜8元素的环；m是0〜2的整数，A环是取代/未取代的碳环或杂环]【选择图】图1
• 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.