2-(3-methyl-2(3H)-benzothiazolylidene)acetonitrile | 52735-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(3-methyl-2(3H)-benzothiazolylidene)acetonitrile
• 英文别名: (3-methylbenzothiazol-2-ylidene)acetonitrile；(3-methyl-3H-benzothiazol-2-ylidene)-acetonitrile；(3-methyl-3H-benzothiazol-2-yliden)-acetonitrile；(3-Methyl-3H-benzothiazol-2-yliden)-acetonitril；2-(3-Methyl-1,3-benzothiazol-2-ylidene)acetonitrile
• CAS: 52735-84-9
• 化学式: C₁₀H₈N₂S
• 分子量: 188.253
• InChiKey: WOUGFVRFVXJZQF-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C(Solv: benzene (71-43-2))
• 沸点：
  289.6±40.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methyl-2(3H)-benzothiazolylidene)acetonitrile 在 氢溴酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.17h， 生成 2-(6-amino-2-bromo-4-hydroxypyridin-3-yl)-3-methylbenzothiazolium bromide
  参考文献：
  名称：

  6-氨基-2-溴-4-羟基烟碱醛衍生物的合成

  摘要：

  （1,3-二甲基苯并咪唑-2-亚基）-，（3-甲基苯并噻唑-2-亚基）-和（3,4-二甲基噻唑-2-亚基）-乙腈与1-（氰基乙酰基）-3,5酰化发现-二甲基吡唑在环外碳原子处进行，产生适当的2-亚杂亚基-3-氧代戊二腈。在回流的乙酸中用氢溴酸处理制得的二腈，得到苯并咪唑鎓，苯并噻唑鎓和噻唑鎓盐的2-（6-氨基-2-溴-4-羟基-4-羟基吡啶-3-基）取代的季盐。X射线晶体学研究清楚地证实了它们的结构。用过量的硼氢化钠还原这些季盐可得到相应的二氢（对于苯并唑而言）或四氢（对于噻唑而言）衍生物，它们被证明是标题为烟醛的合成等价物。 醛-杂环-hydr-腈-吡啶

  DOI：

  10.1055/s-0030-1258371
• 作为产物：
  描述：

  2-甲硫基苯并噻唑 在 三乙胺 作用下， 以 吡啶 为溶剂， 反应 0.25h， 生成 2-(3-methyl-2(3H)-benzothiazolylidene)acetonitrile
  参考文献：
  名称：

  Twisted Cyanines: A Non-Planar Fluorogenic Dye with Superior Photostability and its Use in a Protein-Based Fluoromodule

  摘要：

  The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffers from low photostability. Here, we report the synthesis of a bridge-substituted version of TO named alpha-CN-TO, where the central methine hydrogen of TO is replaced by an electron withdrawing cyano group, which was expected to decrease the susceptibility of the dye toward singlet oxygen-mediated degradation. An X-ray crystal structure shows that alpha-CN-TO is twisted drastically out of plane, in contrast to TO, which crystallizes in the planar conformation. alpha-CN-TO retains the fluorogenic behavior of the parent dye TO in viscous glycerol/water solvent, but direct irradiation and indirect bleaching studies showed that alpha-CN-TO is essentially inert to visible light and singlet oxygen. In addition, the twisted conformation of alpha-CN-TO mitigates nonspecific binding and fluorescence activation by DNA and a previously selected TO-binding protein and exhibits low background fluorescence in HeLa cell culture. alpha-CN-TO was then used to select a new protein that binds and activates fluorescence from the dye. The new alpha-CN-TO/protein fluoromodule exhibits superior photostability to an analogous TO/protein fluoromodule. These properties indicate that alpha-CN-TO will be a useful fluorogenic dye in combination with specific RNA and protein binding partners for both in vitro and cell-based applications. More broadly, structural features that promote nonplanar conformations can provide an effective method for reducing nonspecific binding of cationic dyes to nucleic acids and other biomolecules.

  DOI：

  10.1021/ja308629w

文献信息

• Yagupol'skii,L.M. et al., Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 1326 - 1329
  作者：Yagupol'skii,L.M. et al.

  DOI：——

  日期：——
• Cyanine dyestuffs
  申请人：ILFORD LTD

  公开号：US02542401A1

  公开（公告）日：1951-02-20
• Van Dormael; Nys, Bulletin des Societes Chimiques Belges, 1950, vol. 59, p. 588,591
  作者：Van Dormael、Nys

  DOI：——

  日期：——
• Twisted Cyanines: A Non-Planar Fluorogenic Dye with Superior Photostability and its Use in a Protein-Based Fluoromodule
  作者：Nathaniel I. Shank、Ha H. Pham、Alan S. Waggoner、Bruce A. Armitage

  DOI：10.1021/ja308629w

  日期：2013.1.9

  The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffers from low photostability. Here, we report the synthesis of a bridge-substituted version of TO named alpha-CN-TO, where the central methine hydrogen of TO is replaced by an electron withdrawing cyano group, which was expected to decrease the susceptibility of the dye toward singlet oxygen-mediated degradation. An X-ray crystal structure shows that alpha-CN-TO is twisted drastically out of plane, in contrast to TO, which crystallizes in the planar conformation. alpha-CN-TO retains the fluorogenic behavior of the parent dye TO in viscous glycerol/water solvent, but direct irradiation and indirect bleaching studies showed that alpha-CN-TO is essentially inert to visible light and singlet oxygen. In addition, the twisted conformation of alpha-CN-TO mitigates nonspecific binding and fluorescence activation by DNA and a previously selected TO-binding protein and exhibits low background fluorescence in HeLa cell culture. alpha-CN-TO was then used to select a new protein that binds and activates fluorescence from the dye. The new alpha-CN-TO/protein fluoromodule exhibits superior photostability to an analogous TO/protein fluoromodule. These properties indicate that alpha-CN-TO will be a useful fluorogenic dye in combination with specific RNA and protein binding partners for both in vitro and cell-based applications. More broadly, structural features that promote nonplanar conformations can provide an effective method for reducing nonspecific binding of cationic dyes to nucleic acids and other biomolecules.
• Synthesis of 6-Amino-2-bromo-4-hydroxynicotinaldehyde Derivatives
  作者：Anton Tverdokhlebov、Alexander Denisenko、Andrey Tolmachev、Yulian Volovenko、Svitlana Shishkina、Oleg Shishkin

  DOI：10.1055/s-0030-1258371

  日期：2011.1

  in refluxing acetic acid afforded 2-(6-amino-2-bromo-4-hydroxypyridin-3-yl)-substituted quaternary salts of benzimidazolium, benzothiazolium, and thiazolium. Their structures were confirmed unambiguously by X-ray crystallographic studies. Reduction of these quaternary salts with excess sodium borohydride yielded the corresponding dihydro (in the case of benzoazoles) or tetrahydro (in the case of thiazole)

  （1,3-二甲基苯并咪唑-2-亚基）-，（3-甲基苯并噻唑-2-亚基）-和（3,4-二甲基噻唑-2-亚基）-乙腈与1-（氰基乙酰基）-3,5酰化发现-二甲基吡唑在环外碳原子处进行，产生适当的2-亚杂亚基-3-氧代戊二腈。在回流的乙酸中用氢溴酸处理制得的二腈，得到苯并咪唑鎓，苯并噻唑鎓和噻唑鎓盐的2-（6-氨基-2-溴-4-羟基-4-羟基吡啶-3-基）取代的季盐。X射线晶体学研究清楚地证实了它们的结构。用过量的硼氢化钠还原这些季盐可得到相应的二氢（对于苯并唑而言）或四氢（对于噻唑而言）衍生物，它们被证明是标题为烟醛的合成等价物。 醛-杂环-hydr-腈-吡啶