5,10,15,20-tetra-(p-methoxyphenyl)-21,23-dithiaporphyrin | 71248-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,10,15,20-tetra-(p-methoxyphenyl)-21,23-dithiaporphyrin
• 英文别名: Tetrakis-(p-methoxyphenyl)-21,23-dithiaporphyrin；2,4,6,8-tetrakis-(4-methoxy-phenyl)-1,5(2,5)-dipyrrola-3,7(2,5)-dithiophena-cyclooctaphane-1(2),4,6,7(8)-tetraene；5,10,15,20-tetrakis-(4-methoxy-phenyl)-21,23-dithia-porphine
• CAS: 71248-63-0
• 化学式: C₄₈H₃₆N₂O₄S₂
• 分子量: 768.957
• InChiKey: OMYHIBRCOKVVRA-PEXKIIHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.82
• 重原子数：
  56.0
• 可旋转键数：
  8.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5,10,15,20-tetra-(p-methoxyphenyl)-21,23-dithiaporphyrin 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.0h， 生成 tetraethyl 5,10,15,20-tetra-(4-carboxylatomethoxy)phenyl-21,23-dithiaporphyrin
  参考文献：
  名称：

  Water Soluble, Core-Modified Porphyrins. 3. Synthesis, Photophysical Properties, and in Vitro Studies of Photosensitization, Uptake, and Localization with Carboxylic Acid-Substituted Derivatives

  摘要：

  Water soluble, core-modified porphyrins 1-5 bearing 1-4 carboxylic acid groups were prepared and evaluated in vitro as photosensitizers for photodynamic therapy. The 21,23-core-modified porphyrins 1-5 gave band I absorption maxima with lambda(max) of 695-701 nm. The number of carboxylic acid groups in the dithiaporphyrins 1-4 had little effect on either absorption maxima (lambda(max) of 696-701 nm for band 1) or quantum yields of singlet oxygen generation [phi(O-1(2)) of 0.74-0.80]. Substituting two Se atoms for S gave a shorter band I absorption maximum (lambda(max) of 695 nm) and a smaller value for the quantum yield for generation of singlet oxygen [phi(O-1(2)) of 0.30]. The phototoxicity of 1-5 was evaluated against R3230AC cells. The phototoxicities of dithiaporphyrin 2, sulfonated thiaporphyrin 30, HPPH, and Photofrin were also evaluated against Colo-26 cells in culture using 4 J cm(-2) of 570-800 nm light. Compound 2 was significantly more phototoxic than sulfonated dithiaporphyrin 30, HPPH, or Photofrin. Cellular uptake was much greater for compounds 1, 2, and 5 relative to compounds 3 and 4. Confocal scanning laser microscopy and double labeling experiments with rhodamine 123 suggested that the mitochondria were an important target for dithiaporphyrins 1 and 2. Inhibition of mitochondrial cytochrome c oxidase activity in whole R3230AC cells was observed in the dark with compounds 1 and 30 and both in the dark and in the light with core-modified porphyrin 2.

  DOI：

  10.1021/jm030136i
• 作为产物：
  描述：

  2,5-bis[1-(4-methoxyphenyl)-1-hydroxymethyl]thiophene 在 三氟化硼乙醚 、 四氯苯醌 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5,10,15,20-tetra-(p-methoxyphenyl)-21,23-dithiaporphyrin
  参考文献：
  名称：

  Water Soluble, Core-Modified Porphyrins. 3. Synthesis, Photophysical Properties, and in Vitro Studies of Photosensitization, Uptake, and Localization with Carboxylic Acid-Substituted Derivatives

  摘要：

  Water soluble, core-modified porphyrins 1-5 bearing 1-4 carboxylic acid groups were prepared and evaluated in vitro as photosensitizers for photodynamic therapy. The 21,23-core-modified porphyrins 1-5 gave band I absorption maxima with lambda(max) of 695-701 nm. The number of carboxylic acid groups in the dithiaporphyrins 1-4 had little effect on either absorption maxima (lambda(max) of 696-701 nm for band 1) or quantum yields of singlet oxygen generation [phi(O-1(2)) of 0.74-0.80]. Substituting two Se atoms for S gave a shorter band I absorption maximum (lambda(max) of 695 nm) and a smaller value for the quantum yield for generation of singlet oxygen [phi(O-1(2)) of 0.30]. The phototoxicity of 1-5 was evaluated against R3230AC cells. The phototoxicities of dithiaporphyrin 2, sulfonated thiaporphyrin 30, HPPH, and Photofrin were also evaluated against Colo-26 cells in culture using 4 J cm(-2) of 570-800 nm light. Compound 2 was significantly more phototoxic than sulfonated dithiaporphyrin 30, HPPH, or Photofrin. Cellular uptake was much greater for compounds 1, 2, and 5 relative to compounds 3 and 4. Confocal scanning laser microscopy and double labeling experiments with rhodamine 123 suggested that the mitochondria were an important target for dithiaporphyrins 1 and 2. Inhibition of mitochondrial cytochrome c oxidase activity in whole R3230AC cells was observed in the dark with compounds 1 and 30 and both in the dark and in the light with core-modified porphyrin 2.

  DOI：

  10.1021/jm030136i

文献信息

• Convenient synthetic route of versatile 21-monothiatetraphenylporphyrins of the A4 and AB3 type
  作者：Silvio Stute、Kerstin Gloe、Karsten Gloe

  DOI：10.1016/j.tet.2005.01.037

  日期：2005.3

  A novel convenient synthetic route for poly-functional 21-monothiatetraphenylporphyrins of the type A(4) und AB(3) having base labile substituents in meso position was developed. Using this method a series of symmetric and asymmetric 21-thiaporphyrins containing different functional groups at the meso position is reported. The new products were characterized by NMR, UV-Vis and mass spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.
• Ulman,A.; Manassen,J., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1066 - 1069
  作者：Ulman,A.、Manassen,J.

  DOI：——

  日期：——