2-methyl-1-azathioxanthone | 96331-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methyl-1-azathioxanthone
• 英文别名: 2-methyl-thiochromeno[2,3-b]pyridin-5-one；3-Methyl-4-azathioxanthon；2-methylthiochromeno[2,3-b]pyridin-5-one
• CAS: 96331-65-6
• 化学式: C₁₃H₉NOS
• 分子量: 227.287
• InChiKey: NLHXVNXTYWYVGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-1-azathioxanthone 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 63.0h， 生成 ethyl (2S)-2-[[2-[7-[2-[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]-4-[(5-oxothiochromeno[2,3-b]pyridin-2-yl)methyl]-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  A Europium Complex That Selectively Stains Nucleoli of Cells

  摘要：

  A europium complex selectively staining the nucleolus of NIH 3T3, HeLa, and HDF cells is reported. This complex possesses not only the advantage of the long lifetime of europium emission (0.3 ms), but also a chromophore that allows excitation at a relatively long wavelength (lambda(max) = 384 nm) and gives rise to an acceptable quantum yield (9%). The complex can be used both in live cell and fixed cell imaging, giving an average intracellular concentration on the order of 0.5 mu M. Strong binding to serum albumin has been demonstrated by examination of the analogous gadolinium complex, studying relaxivity changes with increasing protein concentration. The intracellular speciation of the complex has been examined by circularly polarized emission spectroscopy and is consistent with the presence of more than one europium species, possibly protein bound.

  DOI：

  10.1021/ja056303g
• 作为产物：
  描述：

  2-氯-6-甲基烟酸 在 PPA 、 potassium carbonate 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2-methyl-1-azathioxanthone
  参考文献：
  名称：

  Azaxanthones and azathioxanthones are effective sensitisers for europium and terbium luminescence

  摘要：

  几种紫茄素和亚硫紫茄素敏化色素已被纳入大环配体中，并在极性介质中形成了明确的铕和铽复合物。在330到382纳米的范围内激发杂环色素，会产生适量的芳香荧光和相对高效的金属基发光，在水介质中金属基量子产率高达24%。

  DOI：

  10.1039/b601357k

文献信息

• Azaxanthones and azathioxanthones are effective sensitisers for europium and terbium luminescence
  作者：Paul Atkinson、Karen S. Findlay、Filip Kielar、Robert Pal、David Parker、Robert A. Poole、Horst Puschmann、Siobhan L. Richardson、Philip A. Stenson、Amber L. Thompson、Junhau Yu

  DOI：10.1039/b601357k

  日期：——

  Several azaxanthone and azathioxanthone sensitising chromophores have been incorporated into macrocyclic ligands and form well-defined Eu and Tb complexes in polar media. Excitation of the heterocyclic chromophore in the range 330 to 382 nm leads to modest amounts of aromatic fluorescence and relatively efficient metal-based luminescence, with absolute metal-based quantum yields of up to 24% in aqueous media.

  几种紫茄素和亚硫紫茄素敏化色素已被纳入大环配体中，并在极性介质中形成了明确的铕和铽复合物。在330到382纳米的范围内激发杂环色素，会产生适量的芳香荧光和相对高效的金属基发光，在水介质中金属基量子产率高达24%。
• Responsive Luminescent Lanthanide Complexes
  申请人：Parker David

  公开号：US20080312431A1

  公开（公告）日：2008-12-18

  The invention provides a compound comprising a xanthone or thiaxanthone sensitising moiety, capable of coordinating to a lanthanide ion by the nitrogen atom of an integral pyridyl group or a related group able to bind a lanthanide ion.

  本发明提供一种化合物，包括一个黄酮或噻黄酮敏化基团，能够通过一个整体吡啶基团的氮原子或相关能够结合镧系离子的基团与镧系离子配位。
• RESPONSIVE LUMINESCENT LANTHANIDE COMPLEXES
  申请人：UNIVERSITY OF DURHAM

  公开号：EP1885817B1

  公开（公告）日：2016-05-11
• US8193174B2
  申请人：——

  公开号：US8193174B2

  公开（公告）日：2012-06-05
• A Europium Complex That Selectively Stains Nucleoli of Cells
  作者：Junhua Yu、David Parker、Robert Pal、Robert A. Poole、Martin J. Cann

  DOI：10.1021/ja056303g

  日期：2006.2.1

  A europium complex selectively staining the nucleolus of NIH 3T3, HeLa, and HDF cells is reported. This complex possesses not only the advantage of the long lifetime of europium emission (0.3 ms), but also a chromophore that allows excitation at a relatively long wavelength (lambda(max) = 384 nm) and gives rise to an acceptable quantum yield (9%). The complex can be used both in live cell and fixed cell imaging, giving an average intracellular concentration on the order of 0.5 mu M. Strong binding to serum albumin has been demonstrated by examination of the analogous gadolinium complex, studying relaxivity changes with increasing protein concentration. The intracellular speciation of the complex has been examined by circularly polarized emission spectroscopy and is consistent with the presence of more than one europium species, possibly protein bound.