7-(4-fluorophenoxy)thieno[3,2-b]pyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(4-fluorophenoxy)thieno[3,2-b]pyridine
• 英文别名: 7-(4-Fluorophenoxy)thieno[3,2-b]pyridine
• 化学式: C₁₃H₈FNOS
• 分子量: 245.277
• InChiKey: GKLPMUYLXARXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-羟基噻吩并[3,2-b]吡啶 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 caesium carbonate 、 三溴氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 7-(4-fluorophenoxy)thieno[3,2-b]pyridine
  参考文献：
  名称：

  New di(hetero)arylethers and di(hetero)arylamines in the thieno[3,2-b]pyridine series: Synthesis, growth inhibitory activity on human tumor cell lines and non-tumor cells, effects on cell cycle and on programmed cell death

  摘要：

  New fluorinated and methoxylated di(hetero)arylethers and di(hetero)arylamines were prepared functionalizing the 7-position of the thieno[3,2-blpyridine, using copper (C-O) or palladium (C N) catalyzed couplings, respectively, of the 7-bromothieno[3,2-blpyridine, also prepared, with ortho, meta and para fluoro or methoxy phenols and anilines. The compounds obtained were evaluated for their growth inhibitory activity on the human tumor cell lines MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), HCI15 (colon carcinoma), HepG2 (hepatocellular carcinoma) and HeLa (cervical carcinoma). The most active compounds, a di(hetero)arylether with a methoxy group in the meta position relative to the ether function and two di(hetero)arylamines with a methoxy group either in the ortho or in the meta position relative to the NH, were further tested at their GI(50) concentrations on NCI-H460 cells causing pronounced alterations in the cell cycle profile and a strong and significant increase in the programmed death of these cells. The fluorinated and the other methoxylated compounds did not show important activity, presenting high GI(50) values in all the cell lines tested. Furthermore, the hepatotoxicity of the compounds was assessed using porcine liver primary cells (PLP2), established by some of us. Results showed that one of the most active compounds was not toxic to the non-tumor cells at their GI(50) concentrations showing to be the most promising as antitumoral. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.023

文献信息

• Umpolung Synthesis of Pyridyl Ethers by Bi ^V ‐Mediated O‐Arylation of Pyridones
  作者：Katie Ruffell、Liliana C. Gallegos、Kenneth B. Ling、Robert S. Paton、Liam T. Ball

  DOI：10.1002/anie.202212873

  日期：2022.12.19

  We demonstrate that sterically- and electronically-diverse pyridyl ethers can be accessed via BiV-mediated C−O coupling of 2- or 4-pyridones with arylboronic acids. Use of a bismacyclic reagent not only confers modularity on our methodology, but also results in highly regioselective O-arylation that is unprecedented for BiV.

  我们证明可以通过 Bi V介导的 2- 或 4- 吡啶酮与芳基硼酸的 C−O 偶联获得空间和电子多样性的吡啶基醚。双环试剂的使用不仅赋予我们的方法模块化，而且还导致高度区域选择性的 O-芳基化，这对于 Bi V来说是前所未有的。