4,4'-(4,5-dibromo-1,2-phenylene)bis(oxy)bis(methylene)bis(2,2-dimethyl-1,3-dioxolane) | 259820-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4'-(4,5-dibromo-1,2-phenylene)bis(oxy)bis(methylene)bis(2,2-dimethyl-1,3-dioxolane)
• 英文别名: 4-[[4,5-Dibromo-2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenoxy]methyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 259820-97-8
• 化学式: C₁₈H₂₄Br₂O₆
• 分子量: 496.193
• InChiKey: NCVLCQPTBLKIOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-(4,5-dibromo-1,2-phenylene)bis(oxy)bis(methylene)bis(2,2-dimethyl-1,3-dioxolane) 、 copper(l) cyanide 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到4,5-bis[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phthalonitrile
  参考文献：
  名称：

  Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups:  Synthesis and In Vitro Evaluation for Photodynamic Therapy

  摘要：

  Phthalocyanines (Pcs) are a class of photosensitizers (PSs) with a strong tendency to aggregate in aqueous environment, which has a negative influence on their photosensitizing ability in photodynamic therapy. Pcs with either peripheral or axial solketal substituents, that is, ZnPc(sol)(8) and Si(sol)(2)Pc, respectively, were synthesized and their tendency to aggregate as well as their photodynamic properties in 14C and B16F10 cell lines were evaluated. The results were compared to more hydrophilic silicon Pcs, that is, Si(PEG750)(2)Pc and Pc4. The order of cellular uptake was Pc4 > ZnPc(sol)(8) > Si(PEG750)(2)Pc > Si(sol(2))Pc. In contrast, Si(sol(2))Pc showed the highest photocytotoxicity, while ZnPc(sol)(8) did not show any photocytotoxicity up to a concentration of 10 mu M in both cell types. UV/vis spectroscopy showed that Si(sol)(2)Pc is less prone to aggregation than ZnPc(sol)(8), which can explain the lack of photoactivity of the latter. Si(sol)(2)Pc was predominantly located in lipid droplets, whereas Si(PEG750)(2)Pc was homogeneously distributed in the cytosol, which is probably the main cause of their difference in photoactivity. The very high photodynamic efficacy of Si(sol)(2)Pc makes this PS an interesting candidate for future studies.

  DOI：

  10.1021/jm061136w
• 作为产物：
  描述：

  1,2-bis(allyloxy)-4,5-dibromobenzene 在 四氧化锇 、 对甲苯磺酸 、 柠檬酸 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成 4,4'-(4,5-dibromo-1,2-phenylene)bis(oxy)bis(methylene)bis(2,2-dimethyl-1,3-dioxolane)
  参考文献：
  名称：

  Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups:  Synthesis and In Vitro Evaluation for Photodynamic Therapy

  摘要：

  Phthalocyanines (Pcs) are a class of photosensitizers (PSs) with a strong tendency to aggregate in aqueous environment, which has a negative influence on their photosensitizing ability in photodynamic therapy. Pcs with either peripheral or axial solketal substituents, that is, ZnPc(sol)(8) and Si(sol)(2)Pc, respectively, were synthesized and their tendency to aggregate as well as their photodynamic properties in 14C and B16F10 cell lines were evaluated. The results were compared to more hydrophilic silicon Pcs, that is, Si(PEG750)(2)Pc and Pc4. The order of cellular uptake was Pc4 > ZnPc(sol)(8) > Si(PEG750)(2)Pc > Si(sol(2))Pc. In contrast, Si(sol(2))Pc showed the highest photocytotoxicity, while ZnPc(sol)(8) did not show any photocytotoxicity up to a concentration of 10 mu M in both cell types. UV/vis spectroscopy showed that Si(sol)(2)Pc is less prone to aggregation than ZnPc(sol)(8), which can explain the lack of photoactivity of the latter. Si(sol)(2)Pc was predominantly located in lipid droplets, whereas Si(PEG750)(2)Pc was homogeneously distributed in the cytosol, which is probably the main cause of their difference in photoactivity. The very high photodynamic efficacy of Si(sol)(2)Pc makes this PS an interesting candidate for future studies.

  DOI：

  10.1021/jm061136w

文献信息

• Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups:  Synthesis and In Vitro Evaluation for Photodynamic Therapy
  作者：Jan-Willem Hofman、Femke van Zeeland、Selcan Turker、Herre Talsma、Saskia A. G. Lambrechts、Dmitri V. Sakharov、Wim E. Hennink、Cornelus F. van Nostrum

  DOI：10.1021/jm061136w

  日期：2007.4.1

  Phthalocyanines (Pcs) are a class of photosensitizers (PSs) with a strong tendency to aggregate in aqueous environment, which has a negative influence on their photosensitizing ability in photodynamic therapy. Pcs with either peripheral or axial solketal substituents, that is, ZnPc(sol)(8) and Si(sol)(2)Pc, respectively, were synthesized and their tendency to aggregate as well as their photodynamic properties in 14C and B16F10 cell lines were evaluated. The results were compared to more hydrophilic silicon Pcs, that is, Si(PEG750)(2)Pc and Pc4. The order of cellular uptake was Pc4 > ZnPc(sol)(8) > Si(PEG750)(2)Pc > Si(sol(2))Pc. In contrast, Si(sol(2))Pc showed the highest photocytotoxicity, while ZnPc(sol)(8) did not show any photocytotoxicity up to a concentration of 10 mu M in both cell types. UV/vis spectroscopy showed that Si(sol)(2)Pc is less prone to aggregation than ZnPc(sol)(8), which can explain the lack of photoactivity of the latter. Si(sol)(2)Pc was predominantly located in lipid droplets, whereas Si(PEG750)(2)Pc was homogeneously distributed in the cytosol, which is probably the main cause of their difference in photoactivity. The very high photodynamic efficacy of Si(sol)(2)Pc makes this PS an interesting candidate for future studies.