[4-bromo-3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl][4-bromo-3-(4-methoxyphenyl)-5-phenylpyrrol-2-ylidene]amine hydrobromide | 768377-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [4-bromo-3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl][4-bromo-3-(4-methoxyphenyl)-5-phenylpyrrol-2-ylidene]amine hydrobromide
• CAS: 768377-93-1
• 化学式: BrH*C₃₄H₂₅Br₂N₃O₂
• 分子量: 748.311
• InChiKey: QYZYYTJXUTYSFW-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  [4-bromo-3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl][4-bromo-3-(4-methoxyphenyl)-5-phenylpyrrol-2-ylidene]amine hydrobromide 、 三氟化硼乙醚 在 diisopropylethylamine 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到2,8-dibromo-4,4-difluoro-1,7-bis(4-methoxyphenyl)-3,5-diphenyl-4-bora-3a,4a,8-triaza-s-indancene
  参考文献：
  名称：

  In Vitro Demonstration of the Heavy-Atom Effect for Photodynamic Therapy

  摘要：

  Photodynamic therapy (PDT) is an emerging treatment modality for a range of disease classes, both cancerous and noncancerous. This has brought about an active pursuit of new PDT agents that can be optimized for the unique set of photophysical characteristics that are required for a successful clinical agent. We now describe a totally new class of PDT agent, the BF2-chelated 3,5-diaryl-1H-pyrrol-2-yl-3,5-diarylpyrrol-2-yl-ideneamines (tetraarylazadipyrromethenes). Optimized synthetic procedures have been developed to facilitate the generation of an array of specifically substituted derivatives to demonstrate how control of key therapeutic parameters such as wavelength of maximum absorbance and singlet-oxygen generation can be achieved. Photosensitizer absorption maxima can be varied within the body's therapeutic window between 650 and 700 rim, with high extinction coefficients ranging from 75 000 to 85 000 M-1 cm(-1). Photosensitizer singlet-oxygen generation level was modulated by the exploitation of the heavy atom effect. An array of photosensitizers with and without bromine atom substituents gave rise to a series of compounds with varying singlet-oxygen generation profiles. X-ray structural evidence indicates that the substitution of the bromine atoms has not caused a planarity distortion of the photosensitizer. Comparative singlet-oxygen production levels of each photosensitizer versus two standards demonstrated a modulating effect on singlet-oxygen generation depending upon substituent patterns about the photosensitizer. Confocal laser scanning microscopy imaging of 18a in HeLa cervical carcinoma cells proved that the photosensitizer was exclusively localized to the cellular cytoplasm. In vitro light-induced toxicity assays in HeLa cervical carcinoma and MRC5-SV40 transformed fibroblast cancer cell lines confirmed that the heavy-atom effect is viable in a live cellular system and that it can be exploited to modulate assay efficacy. Direct comparison of the efficacy of the photosensitizers 18b and 19b, which only differ in molecular structure by the presence of two bromine atoms, illustrated an increase in efficacy of more than a 1000-fold in both cell lines. All photosensitizers have very low to nondeterminable dark toxicity in our assay system.

  DOI：

  10.1021/ja047649e