4,4'-Di-tert-butyl-1H,1'H-[2,2']bipyrrolyl-5,5'-dicarbaldehyde | 155858-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4'-Di-tert-butyl-1H,1'H-[2,2']bipyrrolyl-5,5'-dicarbaldehyde
• 英文别名: 4,4'-di-tert-butyl-1H,1'H-[2,2'-bipyrrole]-5,5'-dicarbaldehyde
• CAS: 155858-03-0
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: WMKHJQQWTBVZLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.72
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4'-Di-tert-butyl-1H,1'H-[2,2']bipyrrolyl-5,5'-dicarbaldehyde 在 吡啶 、 copper(I) chloride 、 氯磺酸 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 7,17-di-tert-butylporphycene-3,13-di-N-(2-(2-hydroxyethoxy)ethyl)sulfonamide
  参考文献：
  名称：

  A red-light-activated sulfonamide porphycene for highly efficient photodynamic therapy against hypoxic tumor

  摘要：

  Photodynamic therapy (PDT) is an emerging alternative cancer treatment modality that utilizes photo-sensitivity to cause cell death upon photo-irradiation. However, PDT efficiency has been hampered by tumor hypoxia, blue-shifted excitation wavelengths, and the high dark toxicity of photo-sensitizers. We designed and synthesized two novel porphycene-based photosensitizers (TBPoS-OH and TBPoS-2OH) with potent photo-cytotoxicity and a LD₅₀ in the nM range under both normoxic and hypoxic conditions in a variety of cell types after photo-irradiation (λ = 640 ± 15 nm). Further studies showed fast-cellular uptake for TBPoS-OH that localized lysosomes and subsequently induced cell apoptosis via the lysosomal-mitochondrial pathway. Moreover, TBPoS-OH significantly reduced tumor growth in two xenografted mouse models bearing melanoma A375 and B16 cells. Finally, TBPoS-OH exhibited no obvious immunogenicity and toxicity to blood cells and major organs in mice. These data demonstrated that these two porphycene-based photosensitizers, especially TBPoS-OH, could be developed as a potential PDT modality.

  DOI：

  10.1016/j.ejmech.2020.112867
• 作为产物：
  描述：

  3-(tert-butyl)-1-(phenylsulfonyl)-1H-pyrrole 在 2,2,6,6-四甲基哌啶 、 copper(I) chloride 、 正丁基锂 、 magnesium 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 44.0h， 生成 4,4'-Di-tert-butyl-1H,1'H-[2,2']bipyrrolyl-5,5'-dicarbaldehyde
  参考文献：
  名称：

  A red-light-activated sulfonamide porphycene for highly efficient photodynamic therapy against hypoxic tumor

  摘要：

  Photodynamic therapy (PDT) is an emerging alternative cancer treatment modality that utilizes photo-sensitivity to cause cell death upon photo-irradiation. However, PDT efficiency has been hampered by tumor hypoxia, blue-shifted excitation wavelengths, and the high dark toxicity of photo-sensitizers. We designed and synthesized two novel porphycene-based photosensitizers (TBPoS-OH and TBPoS-2OH) with potent photo-cytotoxicity and a LD₅₀ in the nM range under both normoxic and hypoxic conditions in a variety of cell types after photo-irradiation (λ = 640 ± 15 nm). Further studies showed fast-cellular uptake for TBPoS-OH that localized lysosomes and subsequently induced cell apoptosis via the lysosomal-mitochondrial pathway. Moreover, TBPoS-OH significantly reduced tumor growth in two xenografted mouse models bearing melanoma A375 and B16 cells. Finally, TBPoS-OH exhibited no obvious immunogenicity and toxicity to blood cells and major organs in mice. These data demonstrated that these two porphycene-based photosensitizers, especially TBPoS-OH, could be developed as a potential PDT modality.

  DOI：

  10.1016/j.ejmech.2020.112867

文献信息

• The long and winding road to new porphycenes
  作者：Igor Czerski、Arkadiusz Listkowski、Jan Nawrocki、Natalia Urbańska、Hubert Piwoński、Adam Sokołowski、Oksana Pietraszkiewicz、Marek Pietraszkiewicz、Jacek Waluk

  DOI：10.1142/s1088424612500733

  日期：2012.5

  We describe attempts — not always successful — made over the years to improve the efficiency of porphycene synthesis and to produce novel compounds, custom-designed for specific purposes. New porphycenes are reported, some of them obtained rather unexpectedly as by-products of the planned reactions. Structure and energy computations of possible tautomeric forms in porphycenes substituted by one, two, three, and four tert-butyl groups lead to predictions regarding the kinetics and mechanisms of intramolecular double hydrogen transfer. The occurrence of tautomerization in single molecules of tert-butylsubstituted porphycenes is demonstrated by using fluorescence polarization techniques.

  我们介绍了多年来为提高卟吩合成的效率和生产为特定目的定制的新型化合物所做的尝试，这些尝试并不总是成功的。我们还报告了新的卟吩，其中一些卟吩是在计划的反应中意外获得的副产品。通过对被一个、两个、三个和四个叔丁基取代的卟吩中可能存在的同分异构形式进行结构和能量计算，预测了分子内双氢转移的动力学和机理。利用荧光偏振技术证明了叔丁基取代的斑烯类单分子中发生的同分异构现象。
• Lausmann, Michael; Zimmer, Ingeborg; Lex, Johann, Angewandte Chemie, 1994, vol. 106, # 7, p. 776 - 779
  作者：Lausmann, Michael、Zimmer, Ingeborg、Lex, Johann、Lueken, Heiko、Wieghardt, Karl、Vogel, Emanuel

  DOI：——

  日期：——