[3-(4-bromophenyl)-5-phenyl-1H-pyrrol-2-yl][3-(4-bromophenyl)-5-phenylpyrrol-2-ylidene]amine | 603105-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [3-(4-bromophenyl)-5-phenyl-1H-pyrrol-2-yl][3-(4-bromophenyl)-5-phenylpyrrol-2-ylidene]amine
• 英文别名: 3-(4-bromophenyl)-N-[3-(4-bromophenyl)-5-phenyl-1H-pyrrol-2-yl]-5-phenylpyrrol-2-imine
• CAS: 603105-63-1
• 化学式: C₃₂H₂₁Br₂N₃
• 分子量: 607.347
• InChiKey: PWMNBRDZBOSVKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [3-(4-bromophenyl)-5-phenyl-1H-pyrrol-2-yl][3-(4-bromophenyl)-5-phenylpyrrol-2-ylidene]amine 在 N,N-二异丙基乙胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 生成 BF2 chelate of [3-(4-bromophenyl)-5-phenyl-1H-pyrrol-2-yl][3-(4-bromophenyl)-5-phenylpyrrol-2-ylidene]amine
  参考文献：
  名称：

  Synthesis of Aza-BODIPY Boron Difluoride PDT Agents to Promote Apoptosis in HeLa Cells

  摘要：

  BF2螯合的氮杂二吡咯甲烯染料在近红外区域发出荧光，并在光动力疗法中具有潜在应用。当这些氮-BODIPY化合物在600nm以上波长照射下，能与体内的三重态氧反应生成活性单线态氧物种，导致细胞死亡。通过四步合成过程，以苯甲醛和苯乙酮起始环上有不同取代基的条件下，构建了一个小型库，这些潜在的光动力疗法试剂得以合成。在HeLa细胞的体外研究中，发现了一种有效的光敏化合物，其在暗态下具有较低的细胞毒性，并在光照下促进细胞凋亡。

  DOI：

  10.2174/157017811796064377
• 作为产物：
  描述：

  3-(4-溴苯基)-4-硝基-1-苯基丁烷-1-酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 生成 [3-(4-bromophenyl)-5-phenyl-1H-pyrrol-2-yl][3-(4-bromophenyl)-5-phenylpyrrol-2-ylidene]amine
  参考文献：
  名称：

  重氮对氮杂硼-双-吡咯二烯化合物中两个光子吸收性质和系统间交叉机理的影响

  摘要：

  设计并合成了各种位置含溴原子的新型氮杂硼-二吡咯亚甲基化合物，以增强三重态态种群和两个光子吸收特性，可用于二光子光动力疗法，三重态-三重态an灭上转换。稳态荧光和超快泵浦探针光谱技术显示，只有2、6个位置的氮杂硼-二吡咯二烯核心对三重态人口有显着贡献。密度泛函理论计算表明，当将溴原子引入氮杂硼-双-吡咯二烯中心的2、6位时，单线态和三线态能级越近，因此系统间交叉的可能性就越大。在800 nm波长下的Z扫描实验表明，相对于文献中显示出系统间交叉机理的化合物而言，两个光子吸收截面值相当大（610 GM）。有效的系统间穿越和增强的双光子吸收特性使所研究的氮杂硼-二吡咯亚甲基化合物成为双光子光动力疗法应用的良好候选者。

  DOI：

  10.1016/j.dyepig.2015.07.002

文献信息

• Synthesis of Aza-BODIPY Boron Difluoride PDT Agents to Promote Apoptosis in HeLa Cells
  作者：Ronny Priefer、Justin R. Griffiths、Janelle N. Ludwig、Graham Skelhorne-Gross、Robert S. Greene

  DOI：10.2174/157017811796064377

  日期：2011.7.1

  BF2 Chelated azadipyrromethene dyes fluoresce in the near infrared and have potential applications in photodynamic therapy. When irradiated above 600nm these aza-BODIPY compounds react with triplet O2 in the body to form a reactive singlet oxygen species which leads to cell death. A small library has been synthesized of these potential PDT agents via a four step process, with varying substituents on the aromatic ring of the starting benzaldehyde and acetophenone. In vitro studies on HeLa cells have revealed an effective photosensitive compound with low dark cytotoxicity and promotion of apoptotic cell death when exposed to light.

  BF2螯合的氮杂二吡咯甲烯染料在近红外区域发出荧光，并在光动力疗法中具有潜在应用。当这些氮-BODIPY化合物在600nm以上波长照射下，能与体内的三重态氧反应生成活性单线态氧物种，导致细胞死亡。通过四步合成过程，以苯甲醛和苯乙酮起始环上有不同取代基的条件下，构建了一个小型库，这些潜在的光动力疗法试剂得以合成。在HeLa细胞的体外研究中，发现了一种有效的光敏化合物，其在暗态下具有较低的细胞毒性，并在光照下促进细胞凋亡。
• In Vitro Demonstration of the Heavy-Atom Effect for Photodynamic Therapy
  作者：Aoife Gorman、John Killoran、Caroline O'Shea、Tony Kenna、William M. Gallagher、Donal F. O'Shea

  DOI：10.1021/ja047649e

  日期：2004.9.1

  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.
• The effect of heavy atom to two photon absorption properties and intersystem crossing mechanism in aza-boron-dipyrromethene compounds
  作者：Ahmet Karatay、M. Ceren Miser、Xiaoneng Cui、Betül Küçüköz、Halil Yılmaz、Gökhan Sevinç、Elif Akhüseyin、Xueyan Wu、Mustafa Hayvali、H. Gul Yaglioglu、Jianzhang Zhao、Ayhan Elmali

  DOI：10.1016/j.dyepig.2015.07.002

  日期：2015.11

  probability of intersystem crossing increases. Z-scan experiments at 800 nm wavelengths revealed considerably large (610 GM) two photon absorption cross section value with respect to literature for compounds showing intersystem crossing mechanism. The efficient intersystem crossing and enhanced two-photon absorption properties make the investigated aza-boron-dipyrromethene compounds good candidates

  设计并合成了各种位置含溴原子的新型氮杂硼-二吡咯亚甲基化合物，以增强三重态态种群和两个光子吸收特性，可用于二光子光动力疗法，三重态-三重态an灭上转换。稳态荧光和超快泵浦探针光谱技术显示，只有2、6个位置的氮杂硼-二吡咯二烯核心对三重态人口有显着贡献。密度泛函理论计算表明，当将溴原子引入氮杂硼-双-吡咯二烯中心的2、6位时，单线态和三线态能级越近，因此系统间交叉的可能性就越大。在800 nm波长下的Z扫描实验表明，相对于文献中显示出系统间交叉机理的化合物而言，两个光子吸收截面值相当大（610 GM）。有效的系统间穿越和增强的双光子吸收特性使所研究的氮杂硼-二吡咯亚甲基化合物成为双光子光动力疗法应用的良好候选者。
• Near-Infrared Nitrofluorene Substitued Aza-Boron-dipyrromethenes Dyes
  作者：Quentin Bellier、Sarah Pégaz、Christophe Aronica、Boris Le Guennic、Chantal Andraud、Olivier Maury

  DOI：10.1021/ol102701v

  日期：2011.1.7

  The synthesis, spectroscopic properties, and TD-DFT calculations of new aza-Boron-dipyromethene dyes featuring pendant nitrofluorenylethynyl substituents are described. This functionalization allows for moving the luminescence in the NIR, conserving a good quantum yield efficiency.