4,4-difluoro-8-(4-bromophenyl)-2,6-di-iodo-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-8-(4-bromophenyl)-2,6-di-iodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 8-(4-Bromophenyl)-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-(4-bromophenyl)-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: C₁₉H₁₆BBrF₂I₂N₂
• 分子量: 654.87
• InChiKey: MNZZRPWEVQVZOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-8-(4-bromophenyl)-2,6-di-iodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 、 2-溴-5-醛基吡啶 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 2.0h， 以21%的产率得到4,4-difluoro-8-(4-bromophenyl)-1,7-dimethyl-2,6-diiodo-3,5-di-(2-bromopyridylvinyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Diiodinated Mono‐ and Dipyridylvinyl BODIPY Dyes: Photophysicochemical Properties, in vitro Antibacterial Studies, Molecular Docking and Theoretical Calculations

  摘要：

  ABSTRACTIn this study, novel mono‐ and dipyridylvinyl boron dipyrromethene dyes are prepared to compare their photodynamic antimicrobial chemotherapy (PACT) activities against Staphylococcus aureus to the corresponding core dyes. Pyridylvinyl substitution at the 3‐ or 3,5‐positions of a meso‐4‐bromophenylBODIPY core dye via a Knoevenagel reaction with an aromatic 2‐bromopyridinecarboxaldehyde shifts the major BODIPY spectral band to longer wavelength. The extended π‐conjugation red shifts the main spectral band into the 602–618 nm region in CHCl3, THF, ethanol and DMSO after monopyridylvinyl substitution and to 685–704 nm after dipyridylvinyl substitution. An enhancement of the population of the T1 state through the incorporation of iodine atoms at the 2,6‐positions results in moderately high singlet oxygen quantum yields in DMSO. The π‐extended dyes were found to have significantly lower PACT activities than the diiodinated core dye.

  DOI：

  10.1111/php.13698
• 作为产物：
  描述：

  2,2'-[(4-Bromophenyl)methylene]bis(3,5-dimethyl-1H-pyrrole) 在 碘酸 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 4,4-difluoro-8-(4-bromophenyl)-2,6-di-iodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.07.017

文献信息

• Synthesis of a Cationic BODIPY-Containing Conjugated Polymer for Detection of DNA and Cellular Imaging
  作者：Lingyun Wang、Guipo Fang、Derong Cao

  DOI：10.1007/s10895-015-1729-4

  日期：2016.3

  A water-soluble cationic conjugated polyelectrolyte (P1) containing fluorene, BODIPY and diacetylene moieties was synthesized and characterized. P1 showed two main absorption bands with maxima at 360 and 574 nm as well as fluorescence maxima at 648 nm due to the incorporation of BODIPY into the polymer backbone. Addition of CT DNA can quench the emission of P1 because of the formation of a P1/CT DNA complex, which was demonstrated by UV–vis spectra and dynamic light scattering (DLS) analyses. Cellular imaging results indicated P1 could be utilized as cellular imaging of HeLa cells, where red fluorescence was observed in the partial cytoplasm. Moreover, CCK-8 assay showed P1 had a low cytotoxicity.

  合成并表征了一种水溶性阳离子共轭聚电解质（P1），其包含氟烯、BODIPY和二炔基部分。P1显示出两个主要的吸收带，最大吸收波长分别为360和574 nm，并且由于BODIPY的引入，其荧光最大波长为648 nm。加入CT DNA可以淬灭P1的发光，这是由于形成了P1/CT DNA复合物，UV-Vis光谱和动态光散射（DLS）分析验证了这一点。细胞成像结果表明，P1可以作为HeLa细胞的细胞成像探针，在部分细胞质中观察到了红色荧光。此外，CCK-8实验表明P1具有低细胞毒性。
• 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.
• Diiodinated Mono‐ and Dipyridylvinyl <scp>BODIPY</scp> Dyes: Photophysicochemical Properties, <i>in vitro</i> Antibacterial Studies, Molecular Docking and Theoretical Calculations
  作者：Pinar Sen、Azole Sindelo、Nnaemeka Nnaji、John Mack、Tebello Nyokong

  DOI：10.1111/php.13698

  日期：——

  ABSTRACTIn this study, novel mono‐ and dipyridylvinyl boron dipyrromethene dyes are prepared to compare their photodynamic antimicrobial chemotherapy (PACT) activities against Staphylococcus aureus to the corresponding core dyes. Pyridylvinyl substitution at the 3‐ or 3,5‐positions of a meso‐4‐bromophenylBODIPY core dye via a Knoevenagel reaction with an aromatic 2‐bromopyridinecarboxaldehyde shifts the major BODIPY spectral band to longer wavelength. The extended π‐conjugation red shifts the main spectral band into the 602–618 nm region in CHCl3, THF, ethanol and DMSO after monopyridylvinyl substitution and to 685–704 nm after dipyridylvinyl substitution. An enhancement of the population of the T1 state through the incorporation of iodine atoms at the 2,6‐positions results in moderately high singlet oxygen quantum yields in DMSO. The π‐extended dyes were found to have significantly lower PACT activities than the diiodinated core dye.