4-(1H-pyrrol-2-yl)imidazo[4,5-c]pyridin-2-ylamine | 883458-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 4-(1H-pyrrol-2-yl)imidazo[4,5-c]pyridin-2-ylamine
• 英文别名: 4-(1H-pyrrol-2-yl)-1H-imidazo[4,5-c]pyridin-2-ylamine；4-(pyrrole-2-yl)-1H-imidazo[4,5-c]pyridin-2-amine；4-(1H-pyrrol-2-yl)-1H-imidazo[4,5-c]pyridin-2-amine
• CAS: 883458-83-1
• 化学式: C₁₀H₉N₅
• 分子量: 199.215
• InChiKey: BPADIXRUNSRDOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 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：
  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-pyrrol-2-yl)imidazo[4,5-c]pyridin-2-ylamine 、 三氟乙酸 以 乙腈 为溶剂， 生成 4-(pyrrole-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：

  1-benzyloxymethyl-4-bromo-2-methylsulfanyl-5-vinylimidazole 在 palladium on activated charcoal 、 tris(dibenzylideneacetone)dipalladium (0) 吡啶 、 四氯化碳 、 Oxone 、 potassium phosphate 、 正丁基锂 、 sodium azide 、 氢气 、 三苯基膦 、 2-(二环己基膦基)联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 正己烷 、 邻二甲苯 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~145.0 ℃ 、101.33 kPa 条件下， 反应 71.25h， 生成 4-(1H-pyrrol-2-yl)imidazo[4,5-c]pyridin-2-ylamine
  参考文献：
  名称：

  6π-1-氮杂三烯电环化策略在海洋海绵代谢产物法拉定A的全合成及合成类似物的生物学评价中的应用

  摘要：

  据报道，具有血管生成抑制作用的海洋代谢产物法拉定A的12步合成。关键步骤包括用于形成吡啶环的6π-1-氮杂三烯电环化以及N -Boc-吡咯-2-硼酸与氯咪唑并吡啶的Suzuki-Miyaura偶联。另外，描述了在该合成过程中制备的多种拉德金定A的合成类似物的生物活性的评估。

  DOI：

  10.1021/jo0707232

文献信息

• [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。
• Synthesis and anticancer activities of ageladine A and structural analogs
  作者：Yuelong Ma、Sangkil Nam、Richard Jove、Kenichi Yakushijin、David A. Horne

  DOI：10.1016/j.bmcl.2009.11.036

  日期：2010.1

  ageladine A analogs that include 2-aminoimidazo[4,5-c]azepines (seven-membered rings) and 2-amino-3H-imidazo[4,5-c]pyridine (six-membered rings) derivatives were synthesized and evaluated for their anticancer effects against several human cancer cell lines and MMP-2 inhibition in vitro. Only compounds possessing the aromatic azepine (seven-membered ring) core showed anticancer activity with IC50 values

  一系列ageladine A类似物的包括2-氨基咪唑并[4,5- Ç ]氮杂（七元环）和2-氨基-3- ħ -咪唑并[4,5- Ç ]吡啶（六元环）衍生物是合成并评估了它们对几种人类癌细胞系的抗癌作用和体外 MMP-2 抑制作用。只有具有芳香氮杂（七元环）核心的化合物显示出抗癌活性，IC 50值在低微摩尔范围内。
• Total Synthesis of Ageladine A, an Angiogenesis Inhibitor from the Marine Sponge <i>Agelas nakamurai</i>
  作者：Matthew L. Meketa、Steven M. Weinreb

  DOI：10.1021/ol0602304

  日期：2006.3.1

  A 12-step total synthesis of the tricyclic heteroaromatic marine metabolite ageladine A has been achieved using a 6 pi-azaelectrocyclization and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloropyridine as key steps.
• 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.
• Application of a 6π-1-Azatriene Electrocyclization Strategy to the Total Synthesis of the Marine Sponge Metabolite Ageladine A and Biological Evaluation of Synthetic Analogues
  作者：Matthew L. Meketa、Steven M. Weinreb、Yoichi Nakao、Nobuhiro Fusetani

  DOI：10.1021/jo0707232

  日期：2007.6.1

  A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki−Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this

  据报道，具有血管生成抑制作用的海洋代谢产物法拉定A的12步合成。关键步骤包括用于形成吡啶环的6π-1-氮杂三烯电环化以及N -Boc-吡咯-2-硼酸与氯咪唑并吡啶的Suzuki-Miyaura偶联。另外，描述了在该合成过程中制备的多种拉德金定A的合成类似物的生物活性的评估。