semisquaraine of N-ethyl benzothiazole | 149996-92-9

• 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: semisquaraine of N-ethyl benzothiazole
• 英文别名: 3-hydroxy-4-((3-ethylbenzothiazol-2(3H)-ylidene)methyl)cyclobut-3-ene-1,2-dione；3-[(3-ethyl-1,3-benzothiazol-2(3H)-ylidene)methyl]-4-hydroxycyclobut-3-ene-1,2-dione；3-[(3-ethyl-1,3-benzothiazol-2-ylidene)methyl]-4-hydroxycyclobut-3-ene-1,2-dione
• CAS: 149996-92-9
• 化学式: C₁₄H₁₁NO₃S
• 分子量: 273.312
• InChiKey: MLIOTAGJAJTILK-UHFFFAOYSA-N

物化性质

• 沸点：
  323.4±52.0 °C(Predicted)
• 密度：
  1.606±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  semisquaraine of N-ethyl benzothiazole 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 28.0h， 生成 4-[[6-[2-[6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]ethynyl]-3-ethyl-1,3-benzothiazol-3-ium-2-yl]methylidene]-2-[(3-ethyl-1,3-benzothiazol-2-ylidene)methyl]-3-oxocyclobuten-1-olate
  参考文献：
  名称：

  脱氧核糖核苷修饰的海藻酸作为近红外粘度传感器

  摘要：

  脱氧核糖核苷修饰的方酸是通过Sonogashira偶联反应使用不对称的末端炔基化苯并噻唑鎓方酸染料合成的。这些非天然核苷在粘性条件下具有荧光“开启”特性，增强了300倍以上。粘度依赖性荧光增强归因于阻碍了方酸探针的分子聚集和分子内键旋转。荧光显微镜允许在细胞有丝分裂的各个阶段观察高粘度区域。

  DOI：

  10.1002/chem.201403003
• 作为产物：
  描述：

  3-乙基-2-甲基苯并噻唑碘化物 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 semisquaraine of N-ethyl benzothiazole
  参考文献：
  名称：

  脱氧核糖核苷修饰的海藻酸作为近红外粘度传感器

  摘要：

  脱氧核糖核苷修饰的方酸是通过Sonogashira偶联反应使用不对称的末端炔基化苯并噻唑鎓方酸染料合成的。这些非天然核苷在粘性条件下具有荧光“开启”特性，增强了300倍以上。粘度依赖性荧光增强归因于阻碍了方酸探针的分子聚集和分子内键旋转。荧光显微镜允许在细胞有丝分裂的各个阶段观察高粘度区域。

  DOI：

  10.1002/chem.201403003

文献信息

• [EN] LONG WAVELENGTH THIOL-REACTIVE FLUOROPHORES<br/>[FR] FLUOROPHORES REAGISSANT A THIOL A LONGUEURS D'ONDES ELEVEES
  申请人：BECTON DICKINSON CO

  公开号：WO2006025887A3

  公开（公告）日：2006-08-10
• Unsymmetrical 2,6-Di-tert-butyl-Substituted Pyrylo-4-squaraines
  作者：V. V. Kurdyukov、I. V. Kurdyukova

  DOI：10.1134/s1070428019010111

  日期：2019.1

  Triethylammonium salt of pyran semisquaraine reacted with N-methyl-substituted heterocyclic salts to give unsymmetrical di-tert-butyl-substituted squarylium dyes. The effect of the terminal heterocycles on the spectral properties of the obtained dyes was studied, and the electronic structure of squaraines and electronic transitions therein were analyzed by quantum chemical methods.
• Synthesis and Characterization of Near-Infrared Absorbing Water Soluble Squaraines and Study of their Photodynamic Effects in DLA Live Cells
  作者：Kulathinte M. Shafeekh、Mohanannair S. Soumya、Moochikkadavath A. Rahim、Annie Abraham、Suresh Das

  DOI：10.1111/php.12236

  日期：2014.5

  AbstractHere, we report the synthesis, photophysical properties and photodynamic effects in DLA live cells of three water soluble squaraine dyes, viz. bisbenzothiazolium squaraine dyes SQMI and SQDI with iodine in one and both benzothiazolium units, respectively, and an unsymmetrical squaraine dye ASQI containing iodinated benzothiazolium and aniline substituents. The diiodinated SQDI showed an anomalous trend in both fluorescence and triplet quantum yields over the monoiodinated SQMI, with SQDI showing higher fluorescence and lower triplet quantum yields compared to SQMI. Nanosecond laser flash photolysis of SQDI and SQMI indicated the formation of triplet excited states with quantum yield of 0.19 and 0.26, respectively. On photoirradiation, both the SQDI and SQMI generate singlet oxygen and it was observed that both dyes undergoing oxidation reactions with the singlet oxygen generated. ASQI which exhibited a lower triplet quantum yield of 0.06 was, however, stable and did not react with the singlet oxygen generated. In vitro cytotoxicity studies of these dyes in DLA live cells were performed using Trypan blue dye exclusion method and it reflect an order of cytotoxicity of SQDI>SQMI>ASQI. Intracellular generation of the ROS was confirmed by dichlorofluorescein assay after the in vitro PDT.
• Deoxyribonucleoside-Modified Squaraines as Near-IR Viscosity Sensors
  作者：Yuanwei Zhang、Xiling Yue、Bosung Kim、Sheng Yao、Kevin D. Belfield

  DOI：10.1002/chem.201403003

  日期：2014.6.10

  Deoxyribonucleoside‐modified squaraines were synthesized by Sonogashira coupling reactions using an unsymmetrical, terminal alkynylated benzothiazolium squaraine dye. These non‐natural nucleosides exhibited fluorescent ‘turn‐on’ properties in viscous conditions with an enhancement of >300‐fold. The viscosity‐dependent fluorescence enhancement was attributed to a combination of hampering both molecular

  脱氧核糖核苷修饰的方酸是通过Sonogashira偶联反应使用不对称的末端炔基化苯并噻唑鎓方酸染料合成的。这些非天然核苷在粘性条件下具有荧光“开启”特性，增强了300倍以上。粘度依赖性荧光增强归因于阻碍了方酸探针的分子聚集和分子内键旋转。荧光显微镜允许在细胞有丝分裂的各个阶段观察高粘度区域。