1-bromo-3-(2'-pyridylthio)benzene | 1258271-18-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-bromo-3-(2'-pyridylthio)benzene
• CAS: 1258271-18-9
• 化学式: C₁₁H₈BrNS
• 分子量: 266.161
• InChiKey: HSUKBUJNCZRVEW-UHFFFAOYSA-N

物化性质

• 沸点：
  376.4±22.0 °C(predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-bromo-3-(2'-pyridylthio)benzene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 O-(四氢-2H-吡喃-2-基)羟基胺 、 N-甲基二环己基胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 、 三氟乙酸 、 tris[tert-butyl]phosphonium tetrafluoroborate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (E)-N-hydroxy-3-(3-(pyridin-2-ylsulfonyl)phenyl)acrylamide
  参考文献：
  名称：

  2-(Phenylsulfonyl)quinoline N -hydroxyacrylamides as potent anticancer agents inhibiting histone deacetylase

  摘要：

  This study reports the design and synthesis of 2-(phenylsulfonyl)quinoline N-hydroxyacrylamides (8a-k). Structure-activity relationship studies focusing on regio-effect of N-hydroxyacrylamide moiety and influence of the sulfonyl linker revealed that N-hydroxy-3-[3-(quinoline-2-sulfonyl)-phenyl]-acrylamide (8f) showed remarkable enzymatic and cellular activity. The GI(50) values of 8f for HL-60, HCT116, PC-3, and A549 cells were found to be 0.29, 0.08, 0.15, and 0.27 mu M, respectively. The compounds are therefore more potent than FDA approved PXD-101 and SAHA. They also have an effect on the acetylation degree of histone H3 and alpha-tubulin. In in vivo studies, 8f showed marked inhibition of the growth of HCT116 xenografts. (C) 2016 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2016.06.023
• 作为产物：
  描述：

  2-氯吡啶 、 3-溴苯硫酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-bromo-3-(2'-pyridylthio)benzene
  参考文献：
  名称：

  2-(Phenylsulfonyl)quinoline N -hydroxyacrylamides as potent anticancer agents inhibiting histone deacetylase

  摘要：

  This study reports the design and synthesis of 2-(phenylsulfonyl)quinoline N-hydroxyacrylamides (8a-k). Structure-activity relationship studies focusing on regio-effect of N-hydroxyacrylamide moiety and influence of the sulfonyl linker revealed that N-hydroxy-3-[3-(quinoline-2-sulfonyl)-phenyl]-acrylamide (8f) showed remarkable enzymatic and cellular activity. The GI(50) values of 8f for HL-60, HCT116, PC-3, and A549 cells were found to be 0.29, 0.08, 0.15, and 0.27 mu M, respectively. The compounds are therefore more potent than FDA approved PXD-101 and SAHA. They also have an effect on the acetylation degree of histone H3 and alpha-tubulin. In in vivo studies, 8f showed marked inhibition of the growth of HCT116 xenografts. (C) 2016 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2016.06.023

文献信息

• Metal-Free <i>ortho</i>-Selective C–H Borylation of 2-Phenylthiopyridines Using BBr₃
  作者：Gaorong Wu、Binghan Pang、Yangyang Wang、Li Yan、Lu Chen、Tao Ma、Yafei Ji

  DOI：10.1021/acs.joc.1c00520

  日期：2021.4.16

  2-phenylthiopyridines using BBr3 as the boron source under metal-free conditions has been reported. The reaction exhibited site exclusivity, and the synthesized aryl boronates were freely converted to various useful intermediates. Thus, this facile method would be beneficial to synthesize structurally diversified phenylthioethers derivatives and other materials containing boron-nitrogen coordination.

  已经报道了一种在无金属条件下使用BBr 3作为硼源对2-苯基硫代吡啶进行邻位C-H硼化的新途径。该反应表现出位点排他性，并且合成的硼酸芳基酯被自由地转化成各种有用的中间体。因此，这种简便的方法将有利于合成结构上多样化的苯硫醚衍生物和其他含有硼-氮配位的材料。
• Manganese(II), Nickel(II), and Palladium(II) Complexes of a Terpyridine-Like Ligand Containing a Sulfur Linkage, and an Analogous NCN Pincer Palladium(II) Complex: Synthesis, Characterization, and Pd-Catalyzed Reactions
  作者：Masakazu Hirotsu、Yuhei Tsukahara、Isamu Kinoshita

  DOI：10.1246/bcsj.20100076

  日期：2010.9.15

  Coordination properties of new polypyridines containing a single sulfur linkage, 6-(2′′-pyridylthio)-2,2′-bipyridine (L1) and 1-(2′-pyridyl)-3-(2′′-pyridylthio)benzene (HL2), are described. The man...

  含有单硫键的新型聚吡啶、6-(2''-吡啶硫基)-2,2'-联吡啶 (L1) 和 1-(2'-吡啶基)-3-(2''-吡啶硫基)苯的配位性质(HL2)，进行了描述。男人...