5-溴-1-乙基-1H-吡咯并[2,3-b]吡啶 | 1256956-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 5-溴-1-乙基-1H-吡咯并[2,3-b]吡啶
• 英文名称: 5-bromo-7-aza-N-ethylindole
• 英文别名: 5-bromo-1-ethyl-1H-pyrrolo[2,3-b]pyridine；5-bromo-1-ethylpyrrolo[2,3-b]pyridine
• CAS: 1256956-81-6
• 化学式: C₉H₉BrN₂
• 分子量: 225.088
• InChiKey: HQELCDZYBADEEP-UHFFFAOYSA-N

物化性质

• 沸点：
  305.3±22.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-溴-1-乙基-1H-吡咯并[2,3-b]吡啶 在 正丁基锂 、 palladium 10% on activated carbon 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 3-(1-Ethylpyrrolo[2,3-b]pyridin-5-yl)chromen-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2,4,5-Substituted Pyrimidines as a New Class of Tubulin Polymerization Inhibitors

  摘要：

  Members of a series of 2,4,5-substituted pyrimidine derivatives were synthesized, and their interactions with tubulin and their antiproliferative activities against the human hepatocellular carcinoma cells of liver (BEL-7402) were evaluated. One member of this family, the indole-pyrimidine 4k, having an indole-aryl-substituted aminopyrimidine structure, was observed to be an excellent inhibitor of tubulin polymerization (IC50 = 0.79 mu M) and to display significantly high antiproliferative activities against several cancer cell lines with IC50 values ranging from 16 to 62 nM. This substance displayed a high propensity to arrests cells at the G(2)/M phase of the cell cycle (EC50 = 20 nM). In addition, 4k was found to competitively inhibit colchicine binding to tubulin, indicating that it binds to the colchicine-binding site of tubulin. The observations made in this investigation demonstrate that 2,4,5-substituted pyrimidines represent a new class of tubulin polymerization inhibitors with significant antiproliferative activity.

  DOI：

  10.1021/jm101388d
• 作为产物：
  描述：

  5-溴-7-氮杂吲哚 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-溴-1-乙基-1H-吡咯并[2,3-b]吡啶
  参考文献：
  名称：

  10.1021/acs.joc.3c02561

  摘要：

  DOI：

  10.1021/acs.joc.3c02561

文献信息

• Discovery of 3,4-Dihydrobenzo[<i>f</i>][1,4]oxazepin-5(2<i>H</i>)-one Derivatives as a New Class of Selective TNIK Inhibitors and Evaluation of Their Anti-Colorectal Cancer Effects
  作者：Yueshan Li、Liting Zhang、Ruicheng Yang、Zeen Qiao、Ming Wu、Chong Huang、Chenyu Tian、Xinling Luo、Wei Yang、Yun Zhang、Linli Li、Shengyong Yang

  DOI：10.1021/acs.jmedchem.1c00672

  日期：2022.2.10

  colorectal cancer (CRC) that is often associated with dysregulation of Wnt/β-catenin signaling pathway. Herein, we report the discovery of a series of 3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one derivatives as a new class of TNIK inhibitors. Structure–activity relationship (SAR) analyses led to the identification of a number of potent TNIK inhibitors with compound 21k being the most active one (IC50:

  Traf2 和 Nck 相互作用蛋白激酶 (TNIK) 是 Wnt/β-catenin 通路的下游信号蛋白，被认为是治疗结直肠癌 (CRC) 的潜在靶点，结直肠癌通常与Wnt/β-连环蛋白信号通路。在此，我们报告发现了一系列 3,4-二氢苯并[ f ][1,4]oxazep​​in-5(2 H )-one 衍生物作为一类新型 TNIK 抑制剂。构效关系 (SAR) 分析鉴定出许多有效的 TNIK 抑制剂，其中化合物21k是最活跃的一种 (IC 50 : 0.026 ± 0.008 μM)。该化合物还对 TNIK 对 406 种其他激酶表现出优异的选择性。在体外试验中，化合物21k可以有效抑制 CRC 细胞增殖和迁移，并在 HCT116 异种移植小鼠模型中表现出相当大的抗肿瘤活性。它还显示出良好的药代动力学特性。总体而言， 21k可能是针对 TNIK 药物发现的有前途的先导化合物，值得进一步研究。
• Pd(0)-catalyzed benzylic arylation–oxidation of 4-methylquinazolines via sp3 C–H activation under air conditions
  作者：Dan Zhao、Min-Xue Zhu、Yue Wang、Qi Shen、Jian-Xin Li

  DOI：10.1039/c3ob41488d

  日期：——

  An efficient and selective Pd(0)-catalyzed sp3 C–H bond arylation–oxidation of 4-methylquinazolines is reported. The method enables the introduction of arylketone at the benzylic position of 4-methylquinazolines without the use of an additional directing group, and atmospheric oxygen is used as the sole oxidant.

  报道了一种高效且选择性的Pd(0)催化的4-甲基喹唑啉sp³ C–H键芳基化–氧化方法。该方法能够在4-甲基喹唑啉的苄位引入芳基酮，无需额外的诱导基团，并且使用大气中的氧作为唯一的氧化剂。
• Benzoxazepines as Inhibitors of PI3K/mTOR and Methods of Their Use and Manufacture
  申请人：Rice Kenneth D.

  公开号：US20140080810A1

  公开（公告）日：2014-03-20

  The invention is directed to Compounds of Formula I: (I) and pharmaceutically acceptable salts or solvates thereof, as well as methods of treating using the compounds, methods for screening for inhibitor compounds and methods for identifying treatment regimens.

  本发明涉及化合物I式：（I）及其药学上可接受的盐或溶剂化物，以及使用该化合物进行治疗的方法，筛选抑制剂化合物的方法和确定治疗方案的方法。
• BENZOXAZEPINES BASED P13K/MT0R INHIBITORS AGAINST PROLIFERATIVE DISEASES
  申请人：Exelixis, Inc.

  公开号：EP2432779A1

  公开（公告）日：2012-03-28
• BENZOXAZEPINES AS INHIBITORS OF PI3K/MTOR AND METHODS OF THEIR USE AND MANUFACTURE
  申请人：Exelixis, Inc.

  公开号：EP2640366A2

  公开（公告）日：2013-09-25