6-甲基-2-苯基硫烷基吡啶-3-羧酸 | 91718-65-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 6-甲基-2-苯基硫烷基吡啶-3-羧酸
• 英文名称: 6-methyl-2-thiophenoxynicotinic acid
• 英文别名: 2-Methyl-5-carboxy-6-phenylthiopyridin；3-Pyridinecarboxylic acid, 6-methyl-2-(phenylthio)-；6-methyl-2-phenylsulfanylpyridine-3-carboxylic acid
• CAS: 91718-65-9
• 化学式: C₁₃H₁₁NO₂S
• mdl: MFCD00446222
• 分子量: 245.302
• InChiKey: XHFRWZHWRQHZET-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  409.7±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  75.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-甲基-2-苯基硫烷基吡啶-3-羧酸 在 N-溴代丁二酰亚胺(NBS) 、 PPA 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 67.0h， 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 、 苯硫酚 在 potassium carbonate 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70 %的产率得到6-甲基-2-苯基硫烷基吡啶-3-羧酸
  参考文献：
  名称：

  1‐Azathioxanthone Appended Lanthanide(III) DO3A Complexes That Luminesce Following Excitation at 405 nm**

  摘要：

  摘要自塞尔文的首份报告发表以来，我们一直对镧系元素发光在生物成像中的应用潜力着迷。镧系元素独特的窄发射线和长发光寿命为无背景图像和探针定位提供了可能性。以镧系元素为基础的生物成像技术的普遍应用首先受到亮度低的挑战，后来又因为需要使用商用显微镜不具备的紫外线（405 nm）激发光源而受到质疑。在这里，我们根据已知的图案设计了三种基于镧系元素的成像探针，以研究 405 纳米激发的局限性。我们对这些探针进行了合成、表征，在专用显微镜和商用显微镜上进行了研究，并详细探讨了它们的光物理特性。结果毫无疑问地证明，镧系元素复合物可以进入细胞内部发光。即便如此，在商用显微镜上也没有发现镧系元素发光。因此，我们又回到了光物理特性上，从而得出结论：尽管光源和光电探测器取得了进步，但在利用镧系元素发光进行生物成像之前，我们需要新的设计，使镧系元素复合物的亮度更高。

  DOI：

  10.1002/ejic.202300245

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.