2,6-diiodo-1,3,5,7-tetramethyl-8-(2,3,4,5,6-pentafluorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1434003-51-6

• 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: 2,6-diiodo-1,3,5,7-tetramethyl-8-(2,3,4,5,6-pentafluorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-8-pentafluorophenyl-2,6-di-iodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene；4,4-difluoro-2,6-diiodo-1,3,5,7-tetramethyl-8-(2′,3′,4′,5′,6′-pentafluorophenyl)-4-bora-3a,4a-diaza-s-indacene；2,2-Difluoro-5,11-diiodo-4,6,10,12-tetramethyl-8-(2,3,4,5,6-pentafluorophenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene；2,2-difluoro-5,11-diiodo-4,6,10,12-tetramethyl-8-(2,3,4,5,6-pentafluorophenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1434003-51-6
• 化学式: C₁₉H₁₂BF₇I₂N₂
• 分子量: 665.927
• InChiKey: YPMIERJHGZZYET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 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：
  8

反应信息

• 作为反应物：
  描述：

  2,6-diiodo-1,3,5,7-tetramethyl-8-(2,3,4,5,6-pentafluorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 、 4-甲氧基苄硫醇 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以63%的产率得到2,6-diiodo-1,3,5,7-tetramethyl-8-(2,4,5,6-tetrafluoro-3-[(4-methoxybenzyl)sulfanyl]phenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis and photo-physical properties of a series of BODIPY dyes

  摘要：

  A series of 39 boron-dipyrrolylmethenes (BODIPYs) have been synthesized and characterized. Their spectroscopic properties, degree of lipophilicity, chemical stability under irradiation, and singlet-oxygen generation rate have also been studied. These compounds differ in the presence of ethyl groups (group A), hydrogens (group B) or iodines (group C) on the 2,6 positions; these appendices confer particular characteristics to each group. The presence of an aromatic substituent or hydrogen on the indacene 8 position produces 13 different molecules of each group. Besides the effects exerted by the group or atom on the 2,6 positions, the substituent on the 8 position exerts a further effect on the physico-chemical parameters, thus the desired properties of BODIPYs, concerning fluorescence, lipophilicity, and singlet oxygen production can be modulated accordingly. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.064
• 作为产物：
  描述：

  5-pentafluorophenyl-1,3,7,9-tetramethyldipyrrin 在 N-碘代丁二酰亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,6-diiodo-1,3,5,7-tetramethyl-8-(2,3,4,5,6-pentafluorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  卤代 3,5-二甲基- 和 1,3,5,7-四甲基-内消旋-五氟苯基 BODIPY 染料的光动力抗菌活性

  摘要：

  研究了四种内消旋五氟苯基 BODIPY 染料对金黄色葡萄球菌的光动力抗微生物化学疗法 (PACT) 活性，以确定与在 BODIPY 核心上引入不同取代基相关的结构-性质关系。合成并表征了在 2,6 位（2a和3a ）具有溴和碘原子的 1,3,5,7-四甲基染料以及在 1,2,6 位被四溴化的 3,5-二甲基染料,7-位 ( 2b ) 或二碘化 ( 3b) 在 2,6-位置。相对于二溴和四溴染料，在 BODIPY 核心的 2,6 位加入碘原子增强了 PACT 活性。用质子取代 1,7-位的甲基形成3b导致比3a的情况更高的 PACT 活性，因为在 1,7-位不存在与甲基相关的空间位阻允许中间芳基环旋转更接近的平面π-BODIPY 核心系统。四溴化染料被发现具有最低的 PACT 活性，因为它在溶液中缺乏稳定性并且被研究的细菌吸收不良。选择吸电子的五氟苯基来降低 BODIPY 核心染料的偶极矩，因为在用硫代甲基苯基制备

  DOI：

  10.1142/s1088424622500535

文献信息

• 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。
• 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.