4,4-difluoro-2,6-di-iodo-8-(3,5-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-difluoro-2,6-di-iodo-8-(3,5-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-2,6-diiodo-1,3,5,7-tetramethyl-8-(3′,5′-dimethoxyphenyl)-4-Bora-3a,4a-diaza-s-indacene；8-(3,5-Dimethoxyphenyl)-2,2-difluoro-5,11-diiodo-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene；8-(3,5-dimethoxyphenyl)-2,2-difluoro-5,11-diiodo-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• 化学式: C₂₁H₂₁BF₂I₂N₂O₂
• 分子量: 636.027
• InChiKey: XLIFGCUCWSECSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-吲哚甲醛 、 4,4-difluoro-2,6-di-iodo-8-(3,5-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以40%的产率得到
  参考文献：
  名称：

  Synthesis, spectroscopic, and in vitro investigations of 2,6-diiodo-BODIPYs with PDT and bioimaging applications

  摘要：

  A series of five mono-styryl and their corresponding symmetric di-styryl-2,6-diiodo-BODIPYs containing indolyl, pyrrolyl, thienyl or tri(ethylene glycol)phenyl groups were synthesized using Knoevenagel condensations. The yields for the condensation reactions were improved up to 40% using microwave irradiation (90 degrees C for 1 h at 400W) due to lower decomposition of BODIPYs upon prolonged heating. The spectroscopic, structural (including the X-ray of a di-styryl-2,6-diiodo-BODIPY) and in vitro properties of the BODIPYs were investigated. The extension of pi-conjugation through the 3,5-dimethyls of the known phototoxic 2,6-diiodo-BODIPY 1 produced bathochromic shifts in the absorption and emission spectra, in the order of 63-125 nm for the mono-styryl- and 128-220 nm for the di-styryl-BODIPYs in DMSO. The largest red-shifts were observed for the indolyl-containing BODIPYs while the largest fluorescence quantum yields were observed for the tri(ethlileneglycol)phenylstyryl-BODIPYs. Among this series, only the mono-styryl-BODIPYs were phototoxic (IC50= 2-15 mu M at 1.5 J/cm(2)), and were observed to localize preferentially in the cell ER and mitochondria. On the other hand, the di-styryl-BODIPYs were found to have low or no phototoxicity (IC50 > 100 mu M at 1.5 J/cm(2)). Among this series of compounds BODIPY 2a shows the most promise for application as photosensitizer in PDT. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2015.02.006
• 作为产物：
  描述：

  4,4-difluoro-8-(3,5-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 在 碘 、 碘酸 作用下， 以 乙醇 为溶剂， 以74.7%的产率得到4,4-difluoro-2,6-di-iodo-8-(3,5-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  一系列BODIPY的合成，光动力活性和定量构效关系模型

  摘要：

  这里，我们报告的11个新BODIPYs（合成14 - 24），其特征在于通过在8（芳香环的存在内消旋）的位置和碘原子对吡咯2,6位。这些分子中，连同已被我们（报道12个BODIPYs 1  -  12），代表BODIPYs表示不同的原子或基团作为芳族结构部分的取代基的一个大的面板。已经研究了两个物理化学特征（1 O 2生成速率和亲脂性），它们在光敏剂的结果中起着至关重要的作用。在体外在SKOV3细胞系中，在黑暗中处理细胞24小时，然后用绿色LED装置（通量25.2 J / cm 2）照射2 h，研究了23种PS的光诱导杀伤功效。用MTT试验评估细胞杀伤功效，并将其与内消旋未取代化合物之一进行比较（13）。为了理解取代基的可能作用，建立了基于理论整体分子描述符的预测定量构效关系（QSAR）回归模型。结果清楚地表明，芳环的存在是优异的光动力学响应的基础，而芳环上的电子效应和取代基的位置不影响光动力学功效。

  DOI：

  10.1016/j.jphotobiol.2017.01.012

文献信息

• Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs
  作者：Jaime H. Gibbs、Larry T. Robins、Zehua Zhou、Petia Bobadova-Parvanova、Michael Cottam、Gregory T. McCandless、Frank R. Fronczek、M. Graça H. Vicente

  DOI：10.1016/j.bmc.2013.07.017

  日期：2013.9

  A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalization of the BODIPY framework via iodination at the 2,6-pyrrolic positions was explored in order to determine the effect of these heavy atoms on the photophysical and cytotoxicity of the meso-aryl-BODIPYs. BODIPYs bearing meso-thienyl substituents showed the largest red-shifted absorptions and emissions and reduced fluorescence quantum yields. The phototoxicity of the BODIPYs in human carcinoma HEp2 cells depends on both the presence of iodines and the nature of the meso-aryl groups. Six of the eleven 2,6-diiodo-BODIPYs investigated showed at least a sevenfold enhancement in phototoxicity (IC50 = 3.5-28 mu M at 1.5 J/cm(2)) compared with the non-iodinated BODIPYs, while the others showed no cytotoxicity, while their singlet oxygen quantum yields ranged from 0.02 to 0.76. Among the series investigated, BODIPYs 2a and 4a bearing electron-donating meso-dimethoxyphenyl substituents showed the highest phototoxicity and dark/phototoxicity ratio, and are therefore the most promising for application in PDT. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis, photodynamic activity, and quantitative structure-activity relationship modelling of a series of BODIPYs
  作者：Enrico Caruso、Marzia Gariboldi、Alessandro Sangion、Paola Gramatica、Stefano Banfi

  DOI：10.1016/j.jphotobiol.2017.01.012

  日期：2017.2

  Here we report the synthesis of eleven new BODIPYs (14–24) characterized by the presence of an aromatic ring on the 8 (meso) position and of iodine atoms on the pyrrolic 2,6 positions. These molecules, together with twelve BODIPYs already reported by us (1 − 12), represent a large panel of BODIPYs showing different atoms or groups as substituent of the aromatic moiety. Two physico-chemical features

  这里，我们报告的11个新BODIPYs（合成14 - 24），其特征在于通过在8（芳香环的存在内消旋）的位置和碘原子对吡咯2,6位。这些分子中，连同已被我们（报道12个BODIPYs 1  -  12），代表BODIPYs表示不同的原子或基团作为芳族结构部分的取代基的一个大的面板。已经研究了两个物理化学特征（1 O 2生成速率和亲脂性），它们在光敏剂的结果中起着至关重要的作用。在体外在SKOV3细胞系中，在黑暗中处理细胞24小时，然后用绿色LED装置（通量25.2 J / cm 2）照射2 h，研究了23种PS的光诱导杀伤功效。用MTT试验评估细胞杀伤功效，并将其与内消旋未取代化合物之一进行比较（13）。为了理解取代基的可能作用，建立了基于理论整体分子描述符的预测定量构效关系（QSAR）回归模型。结果清楚地表明，芳环的存在是优异的光动力学响应的基础，而芳环上的电子效应和取代基的位置不影响光动力学功效。
• Synthesis, spectroscopic, and in vitro investigations of 2,6-diiodo-BODIPYs with PDT and bioimaging applications
  作者：Jaime H. Gibbs、Zehua Zhou、David Kessel、Frank R. Fronczek、Svetlana Pakhomova、M. Graça H. Vicente

  DOI：10.1016/j.jphotobiol.2015.02.006

  日期：2015.4

  A series of five mono-styryl and their corresponding symmetric di-styryl-2,6-diiodo-BODIPYs containing indolyl, pyrrolyl, thienyl or tri(ethylene glycol)phenyl groups were synthesized using Knoevenagel condensations. The yields for the condensation reactions were improved up to 40% using microwave irradiation (90 degrees C for 1 h at 400W) due to lower decomposition of BODIPYs upon prolonged heating. The spectroscopic, structural (including the X-ray of a di-styryl-2,6-diiodo-BODIPY) and in vitro properties of the BODIPYs were investigated. The extension of pi-conjugation through the 3,5-dimethyls of the known phototoxic 2,6-diiodo-BODIPY 1 produced bathochromic shifts in the absorption and emission spectra, in the order of 63-125 nm for the mono-styryl- and 128-220 nm for the di-styryl-BODIPYs in DMSO. The largest red-shifts were observed for the indolyl-containing BODIPYs while the largest fluorescence quantum yields were observed for the tri(ethlileneglycol)phenylstyryl-BODIPYs. Among this series, only the mono-styryl-BODIPYs were phototoxic (IC50= 2-15 mu M at 1.5 J/cm(2)), and were observed to localize preferentially in the cell ER and mitochondria. On the other hand, the di-styryl-BODIPYs were found to have low or no phototoxicity (IC50 > 100 mu M at 1.5 J/cm(2)). Among this series of compounds BODIPY 2a shows the most promise for application as photosensitizer in PDT. (C) 2015 Elsevier B.V. All rights reserved.