9-Bromopyrido[2,1-c][1,2,4]benzotriazin-11-ium;chloride | 1018945-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 9-Bromopyrido[2,1-c][1,2,4]benzotriazin-11-ium;chloride
• CAS: 1018945-73-7
• 化学式: C₁₁H₇BrN₃*Cl
• 分子量: 296.554
• InChiKey: SLSYVZVQOCXJCJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.87
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-Bromopyrido[2,1-c][1,2,4]benzotriazin-11-ium;chloride 在 sodium dithionite 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以75%的产率得到
  参考文献：
  名称：

  Synthesis of Azoaromatic Dyes via Redox Driven C−N Bond Fusion

  摘要：

  Two novel organic azo-dyes (2(+)) that feature an intense intramolecular charge transfer transition with end absorption reaching into the NIR region are Introduced. Syntheses of these compounds were achieved by an unusual redox-driven C-N bond fusion of the tricyclo azo-aromatic compounds (1(+)). The compounds show reversible electro- as well as proton chromism. The results have generated further scope of research in the area of designed syntheses of functional azoaromatics,

  DOI：

  10.1021/ol9011184
• 作为产物：
  描述：

  2-(4-bromo-phenylazo)-pyridine 在 盐酸 作用下， 以 乙腈 为溶剂， 以64%的产率得到9-Bromopyrido[2,1-c][1,2,4]benzotriazin-11-ium;chloride
  参考文献：
  名称：

  Mild Synthesis of a Family of Planar Triazinium Cations via Proton-Assisted Cyclization of Pyridyl Containing Azo Compounds and Studies on DNA Intercalation

  摘要：

  An efficient synthesis of a family of heteroaromatic triazinium compounds, [2a]X-[2g]X (X= Cl, ClO4, NO3, and HSO4), from 2-(arylazo)pyridines via proton-catalyzed heterocyclization is described. Characterization of the compounds is made by different spectroscopic, electrochemical techniques, as well as single-crystal structure determination of the triflate salt of a representative compound, [2a]CF3SO3. The bond parameters indicate that the tricyclo compound, 2a(+), is planar and aromatic with a N-N bond length of 1.275(6) angstrom. These exhibited fluorescence with an emission maximum in the range of 540-535 nm with moderate quantum yields. The triazinium salts can be reduced in two successive one-electron steps as probed by cyclic voltammetry and coulometry. The paramagnetic radical intermediate 2a(center dot) is distinguished by a sharp and intense EPR spectrum. Fluorescence spectroscopy, circular dichroism, cyclic voltammetry, viscosity measurements, together with DNA melting studies have been used to characterize the binding of 2a+ with calf thymus DNA. The emission quenching of the compound by [Fe(CN)(6)](4-) decreased when bound to DNA. As determined by a MTT assay, 2a+ exhibited significant cytotoxicity at a higher concentration range of 1 mg/mL to 1 mu g/mL; however, the % survival ratio increased with dilution. Cellular uptake studies of the referenced compound were followed by FACS analysis.

  DOI：

  10.1021/ja710211u

文献信息

• Mild Synthesis of a Family of Planar Triazinium Cations via Proton-Assisted Cyclization of Pyridyl Containing Azo Compounds and Studies on DNA Intercalation
  作者：M. Sinan、M. Panda、A. Ghosh、K. Dhara、P. E. Fanwick、D. J. Chattopadhyay、S. Goswami

  DOI：10.1021/ja710211u

  日期：2008.4.1

  An efficient synthesis of a family of heteroaromatic triazinium compounds, [2a]X-[2g]X (X= Cl, ClO4, NO3, and HSO4), from 2-(arylazo)pyridines via proton-catalyzed heterocyclization is described. Characterization of the compounds is made by different spectroscopic, electrochemical techniques, as well as single-crystal structure determination of the triflate salt of a representative compound, [2a]CF3SO3. The bond parameters indicate that the tricyclo compound, 2a(+), is planar and aromatic with a N-N bond length of 1.275(6) angstrom. These exhibited fluorescence with an emission maximum in the range of 540-535 nm with moderate quantum yields. The triazinium salts can be reduced in two successive one-electron steps as probed by cyclic voltammetry and coulometry. The paramagnetic radical intermediate 2a(center dot) is distinguished by a sharp and intense EPR spectrum. Fluorescence spectroscopy, circular dichroism, cyclic voltammetry, viscosity measurements, together with DNA melting studies have been used to characterize the binding of 2a+ with calf thymus DNA. The emission quenching of the compound by [Fe(CN)(6)](4-) decreased when bound to DNA. As determined by a MTT assay, 2a+ exhibited significant cytotoxicity at a higher concentration range of 1 mg/mL to 1 mu g/mL; however, the % survival ratio increased with dilution. Cellular uptake studies of the referenced compound were followed by FACS analysis.
• Synthesis of Azoaromatic Dyes via Redox Driven C−N Bond Fusion
  作者：Mominul Sinan、Manashi Panda、Priyabrata Banerjee、C. B. Shinisha、Raghavan B. Sunoj、Sreebrata Goswami

  DOI：10.1021/ol9011184

  日期：2009.8.6

  Two novel organic azo-dyes (2(+)) that feature an intense intramolecular charge transfer transition with end absorption reaching into the NIR region are Introduced. Syntheses of these compounds were achieved by an unusual redox-driven C-N bond fusion of the tricyclo azo-aromatic compounds (1(+)). The compounds show reversible electro- as well as proton chromism. The results have generated further scope of research in the area of designed syntheses of functional azoaromatics,