4,4-difluoro-1,3,5,7-tetramethyl-8-(4-(3,6,9-trioxa-9-propargylnonoxy)phenyl)-4-bora-3a,4a-diaza-s-indacene | 1471991-82-8

• 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-difluoro-1,3,5,7-tetramethyl-8-(4-(3,6,9-trioxa-9-propargylnonoxy)phenyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 2,2-Difluoro-4,6,10,12-tetramethyl-8-[4-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]phenyl]-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene；2,2-difluoro-4,6,10,12-tetramethyl-8-[4-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]phenyl]-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1471991-82-8
• 化学式: C₂₈H₃₃BF₂N₂O₄
• 分子量: 510.389
• InChiKey: IKHOVSINJDGLGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  44.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-1,3,5,7-tetramethyl-8-(4-(3,6,9-trioxa-9-propargylnonoxy)phenyl)-4-bora-3a,4a-diaza-s-indacene 在 碘 、 碘酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以80%的产率得到4,4-difluoro-2,6-diiodo-1,3,5,7-tetramethyl-8-(4-(3,6,9-trioxa-9-propargylnonoxy)-phenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Preparation and in Vitro Photodynamic Activities of Folate-Conjugated Distyryl Boron Dipyrromethene Based Photosensitizers

  摘要：

  Two folate-conjugated diiododistyryl boron dipyrromethenes have been prepared and characterized with various spectroscopic methods. These conjugates exhibit higher photocytotoxicity toward the KB human nasopharyngeal carcinoma cells, which have high expression of folate receptors When compared with the MCF-7 human breast adenocarcinoma cells, which have low expression of folate receptors. The difference in photocytotoxicity for these two cell lines is particularly large for the conjugate with a shorter oligoethylene glycol linker (compound 11a) as a result of its higher cellular uptake and slightly lower aggregation tendency. Its IC50 value toward KB cells (0.06 mu M) is 43-fold lower than analogue with a longer linker (compound 11b). The length compound 11a shows high affinity toward the endoplasmic lysosomes. that for MCF-7 cells, while the difference is only 6-fold for the of the spacer also affects their subcellular localization. While eticulum of KB cells, conjugate 11b is mainly localized in the lysosomes.

  DOI：

  10.1021/jm4009168
• 作为产物：
  描述：

  4,4-difluoro-1,3,5,7-tetramethyl-8-(4-hydroxyphenyl)-4-bora-3a,4a-diaza-s-indacene 、 丙炔基-PEG4-对甲苯磺酸酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以63%的产率得到4,4-difluoro-1,3,5,7-tetramethyl-8-(4-(3,6,9-trioxa-9-propargylnonoxy)phenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Preparation and in Vitro Photodynamic Activities of Folate-Conjugated Distyryl Boron Dipyrromethene Based Photosensitizers

  摘要：

  Two folate-conjugated diiododistyryl boron dipyrromethenes have been prepared and characterized with various spectroscopic methods. These conjugates exhibit higher photocytotoxicity toward the KB human nasopharyngeal carcinoma cells, which have high expression of folate receptors When compared with the MCF-7 human breast adenocarcinoma cells, which have low expression of folate receptors. The difference in photocytotoxicity for these two cell lines is particularly large for the conjugate with a shorter oligoethylene glycol linker (compound 11a) as a result of its higher cellular uptake and slightly lower aggregation tendency. Its IC50 value toward KB cells (0.06 mu M) is 43-fold lower than analogue with a longer linker (compound 11b). The length compound 11a shows high affinity toward the endoplasmic lysosomes. that for MCF-7 cells, while the difference is only 6-fold for the of the spacer also affects their subcellular localization. While eticulum of KB cells, conjugate 11b is mainly localized in the lysosomes.

  DOI：

  10.1021/jm4009168