4-[1,3]dioxolan-2-yl-3,5-difluoropyridine | 924649-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[1,3]dioxolan-2-yl-3,5-difluoropyridine
• 英文别名: 4-(1,3-Dioxolan-2-yl)-3,5-difluoropyridine
• CAS: 924649-14-9
• 化学式: C₈H₇F₂NO₂
• 分子量: 187.146
• InChiKey: RWBUHQBRMCFUOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[1,3]dioxolan-2-yl-3,5-difluoropyridine 在 盐酸 作用下， 生成 3,5-二氟吡啶-4-甲醛
  参考文献：
  名称：

  Synthesis and in vitro photodynamic activities of water-soluble fluorinated tetrapyridylporphyrins as tumor photosensitizers

  摘要：

  A series of water-soluble fluorinated cationic porphyrins were designed, synthesized, and characterized. In vitro photo-cytotoxicity of these compounds was evaluated by MTT assay on HeLa cells. Their photocytotoxicity was dependent on the positions of the cations and the fluorines in the pyridine ring, and 5,10,15,20-tetrakis-(N-methyl-2-fluoro-pyridin-3-yl)-porphyrin (8) showed the most potent photo-induced cytotoxicity without photobleaching. PDT-induced ROS inside HeLa cells was measured with flow cytometry using ROS-sensitive fluorometric probe, 2,7-dichlorofluororescin (DCF), which revealed high correlations of ROS with cellular cytotoxicity. FACS analysis shows that PDT with porphyrin 8 induced apoptosis in HeLa cells. In summary, efficient generation of ROS, biological effectiveness, and good photostability of porphyrin 8 indicate its potential application in photodynamic therapy (PDT) in the near future. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.083
• 作为产物：
  描述：

  3,5-dibromo-4-[1,3]dioxolan-2-yl-pyridine 在 N-氟代双苯磺酰胺 作用下， 生成 4-[1,3]dioxolan-2-yl-3,5-difluoropyridine
  参考文献：
  名称：

  Synthesis and in vitro photodynamic activities of water-soluble fluorinated tetrapyridylporphyrins as tumor photosensitizers

  摘要：

  A series of water-soluble fluorinated cationic porphyrins were designed, synthesized, and characterized. In vitro photo-cytotoxicity of these compounds was evaluated by MTT assay on HeLa cells. Their photocytotoxicity was dependent on the positions of the cations and the fluorines in the pyridine ring, and 5,10,15,20-tetrakis-(N-methyl-2-fluoro-pyridin-3-yl)-porphyrin (8) showed the most potent photo-induced cytotoxicity without photobleaching. PDT-induced ROS inside HeLa cells was measured with flow cytometry using ROS-sensitive fluorometric probe, 2,7-dichlorofluororescin (DCF), which revealed high correlations of ROS with cellular cytotoxicity. FACS analysis shows that PDT with porphyrin 8 induced apoptosis in HeLa cells. In summary, efficient generation of ROS, biological effectiveness, and good photostability of porphyrin 8 indicate its potential application in photodynamic therapy (PDT) in the near future. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.083

文献信息

• Synthesis of difluorinated pyridinecarboxaldehyde via electrophilic fluorination
  作者：Yoon-Joo Ko、Kyung-Bae Park、Seung-Bo Shim、Jung-Hyu Shin

  DOI：10.1016/j.jfluchem.2006.02.009

  日期：2006.6

  An efficient synthesis of novel 3,5-difluoropyridine-4-carboxaldehyde using N-fluoro-benzenesulfonimide (NSFi) is described. Difluorination was achieved through the reaction of 3,5-dihalo-1,3-dioxolane pyridine with n-butyllithium followed by N-fluorobenzenesulfonimide at -120 degrees C in good to high yields. Maintaining the low temperature during the transmetallation was found to be critical for the selective formation of the difluoro-susbstitution over the monofluoro one. (c) 2006 Elsevier B.V. All rights reserved.
• Synthesis and in vitro photodynamic activities of water-soluble fluorinated tetrapyridylporphyrins as tumor photosensitizers
  作者：Yoon-Joo Ko、Kyung-Jin Yun、Min-Seok Kang、Jongmin Park、Kyung-Tae Lee、Seung Bum Park、Jung-Hyu Shin

  DOI：10.1016/j.bmcl.2007.02.083

  日期：2007.5

  A series of water-soluble fluorinated cationic porphyrins were designed, synthesized, and characterized. In vitro photo-cytotoxicity of these compounds was evaluated by MTT assay on HeLa cells. Their photocytotoxicity was dependent on the positions of the cations and the fluorines in the pyridine ring, and 5,10,15,20-tetrakis-(N-methyl-2-fluoro-pyridin-3-yl)-porphyrin (8) showed the most potent photo-induced cytotoxicity without photobleaching. PDT-induced ROS inside HeLa cells was measured with flow cytometry using ROS-sensitive fluorometric probe, 2,7-dichlorofluororescin (DCF), which revealed high correlations of ROS with cellular cytotoxicity. FACS analysis shows that PDT with porphyrin 8 induced apoptosis in HeLa cells. In summary, efficient generation of ROS, biological effectiveness, and good photostability of porphyrin 8 indicate its potential application in photodynamic therapy (PDT) in the near future. (c) 2007 Elsevier Ltd. All rights reserved.