5'-(4-thienyl-2,1,3-benzothiadiazole)-[2,2']-bithiophenyl-5-carboxylic acid (2,5-dioxopyrrolidin-1-yl) ester | 1042131-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5'-(4-thienyl-2,1,3-benzothiadiazole)-[2,2']-bithiophenyl-5-carboxylic acid (2,5-dioxopyrrolidin-1-yl) ester
• 英文别名: 2,5-dioxopyrrolidin-1-yl-5'-(7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)2-2'bithiophene-5-carboxylate
• CAS: 1042131-68-9
• 化学式: C₂₃H₁₃N₃O₄S₄
• 分子量: 523.638
• InChiKey: QYGGZAIAOXVLGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  89.46
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-噻吩甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 38.08h， 生成 5'-(4-thienyl-2,1,3-benzothiadiazole)-[2,2']-bithiophenyl-5-carboxylic acid (2,5-dioxopyrrolidin-1-yl) ester
  参考文献：
  名称：

  Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils

  摘要：

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

  DOI：

  10.1021/ja2065522