N'-tert-butoxycarbonyl-5'-(2-amino-4,5,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl)-2',3'-dibromopyrrole | 911034-72-5

• 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: N'-tert-butoxycarbonyl-5'-(2-amino-4,5,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl)-2',3'-dibromopyrrole
• 英文别名: N'-tert-butoxycarbonyl-5-(2-amino-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-yl)-2,3-dibromopyrrole；tert-butyl 5-(2-amino-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-4-yl)-2,3-dibromopyrrole-1-carboxylate
• CAS: 911034-72-5
• 化学式: C₁₅H₁₉Br₂N₅O₂
• 分子量: 461.156
• InChiKey: XBQVFGXUWDWOCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  98
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N'-tert-butoxycarbonyl-5'-(2-amino-4,5,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl)-2',3'-dibromopyrrole 在 四氯苯醌 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以50%的产率得到
  参考文献：
  名称：

  Ageladine A及其结构类似物的合成及抗癌活性

  摘要：

  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。

  DOI：

  10.1016/j.bmcl.2009.11.036
• 作为产物：
  描述：

  α-N-Acetyl-2-aminohistamin 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 N'-tert-butoxycarbonyl-5'-(2-amino-4,5,6,7-tetrahydroimidazo[4,5-c]pyridin-4-yl)-2',3'-dibromopyrrole
  参考文献：
  名称：

  一种海绵定碱A盐酸盐的制备方法及海绵定碱A的应用

  摘要：

  本发明公开了一种海绵定碱A盐酸盐的制备方法及海绵定碱A的应用，属于药物应用技术领域。本发明通过将如式8所示的化合物和如式3所示的化合物经过关环、脱氢、脱保护基后最终制得海绵定碱A盐酸盐；本发明还公开了海绵定碱A对非小细胞肺癌A549细胞的药理活性，其明显抑制了A549细胞的生长，增加了铁离子浓度和脂质活性氧，下调了铁死亡相关蛋白，从而诱导了肿瘤细胞铁死亡。

  公开号：

  CN113896726B

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 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。
• 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.
• Concise Total Synthesis of the Marine Natural Product Ageladine A
  作者：Sudhir R. Shengule、Peter Karuso

  DOI：10.1021/ol061584y

  日期：2006.8.1

  A total synthesis of ageladine A has been achieved by exploiting a Pictet-Spengler- type condensation between 2-aminohistamine and 4,5dibromo-2-formylpyrrole as the key step.
• 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。