5,10,15,20-tetraphenyl-21,23-diselenaporphyrin | 66951-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 5,10,15,20-tetraphenyl-21,23-diselenaporphyrin
• 英文别名: Tetraphenyl-21,23-diselenaporphyrin；2,4,6,8-tetraphenyl-1,5(2,5)-dipyrrola-3,7(2,5)-diselenophena-cyclooctaphane-1(2),4,6,7(8)-tetraene；5,10,15,20-tetraphenyl-21,23-diselena-porphine
• CAS: 66951-06-2
• 化学式: C₄₄H₂₈N₂Se₂
• 分子量: 742.64
• InChiKey: DXMQDLHOBMAASZ-RKKMNUGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.78
• 重原子数：
  48.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5,10,15,20-tetraphenyl-21,23-diselenaporphyrin 在 硫酸 作用下， 反应 18.0h， 生成 5,10,15,20-tetrakis(4-sulfonatophenyl)-21,23-diselenaporphyrin
  参考文献：
  名称：

  Water-Soluble, Core-Modified Porphyrins as Novel, Longer-Wavelength-Absorbing Sensitizers for Photodynamic Therapy

  摘要：

  Water-soluble, core-modified 5,10,15,20-tetrakis(4-sulfonatophenyl)-21,23-dithiaporphyrin (1) and 5,10,15,20-tetrakis(4-sulfonatophenyl)-21,23-diselenaporphyrin (2) were prepared as the tetrasodium salts by the sulfonation of 5,10,15,20-tetraphenyl-21,23-dithiaporphyrin (3) and -21,23-diselenaporphyrin (4), respectively, with sulfuric acid. Compounds 3 and 4 were prepared by the condensation of pyrrole with either 2,5-bis(phenylhydroxymethyl)thiophene (5) or 2,5-bis(phenylhydroxymethyl)selenophene (6) in propionic acid. The addition of benzaldehyde to 2,5-dilithiothiophene or 2,5-dilithioselenophene gives 5 or 6, respectively, as a nearly equimolar mixture of meso- and d,l-diastereomers. Careful crystallization of 5 gives a single diastereomer by removing the crystalline product from the equilibrating mixture of diastereomers in solution, Photodynamic therapy (PDT) with 1 has an LD50 of less than 25 mu g/mL against Colo-26 cells in culture and exhibits a lethal dose for 90% or more at concentrations greater than 50 mu g/mL. In contrast, PDT with 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (TPPS4) requires concentrations of greater than 100 mu g/mL to achieve LD50 Neither 1 nor TPPS4 shows significant photoactivity against the murine T-cell line, MOLT-4, above the dark toxicity. Sensitizer 1 shows no toxicity or side effects in BALB/c mice observed for 30 days following a single intravenous injection of 10 mg (9.1 mu mol)/kg. Distribution studies show that sensitizer 1 accumulates in the tumors of BALB/c mice bearing Cole-26 or EMT-6 tumors with sensitizer concentration roughly doubling as the dosage of 1 increased from 5 to 10 mg/kg. In vivo studies show that PDT with sensitizer 1 at both 3.25 and 10 mg/kg with 135 cm(-2) of 694-nm light is effective against Cola-26 tumors in BALB/c mice.

  DOI：

  10.1021/jm000044i
• 作为产物：
  描述：

  吡咯 、 2,5-bis(phenylhydroxymethyl)selenophene 在 乙酸酐 、 丙酸 作用下， 反应 1.0h， 以2.2%的产率得到5,10,15,20-tetraphenyl-21,23-diselenaporphyrin
  参考文献：
  名称：

  Water-Soluble, Core-Modified Porphyrins as Novel, Longer-Wavelength-Absorbing Sensitizers for Photodynamic Therapy

  摘要：

  Water-soluble, core-modified 5,10,15,20-tetrakis(4-sulfonatophenyl)-21,23-dithiaporphyrin (1) and 5,10,15,20-tetrakis(4-sulfonatophenyl)-21,23-diselenaporphyrin (2) were prepared as the tetrasodium salts by the sulfonation of 5,10,15,20-tetraphenyl-21,23-dithiaporphyrin (3) and -21,23-diselenaporphyrin (4), respectively, with sulfuric acid. Compounds 3 and 4 were prepared by the condensation of pyrrole with either 2,5-bis(phenylhydroxymethyl)thiophene (5) or 2,5-bis(phenylhydroxymethyl)selenophene (6) in propionic acid. The addition of benzaldehyde to 2,5-dilithiothiophene or 2,5-dilithioselenophene gives 5 or 6, respectively, as a nearly equimolar mixture of meso- and d,l-diastereomers. Careful crystallization of 5 gives a single diastereomer by removing the crystalline product from the equilibrating mixture of diastereomers in solution, Photodynamic therapy (PDT) with 1 has an LD50 of less than 25 mu g/mL against Colo-26 cells in culture and exhibits a lethal dose for 90% or more at concentrations greater than 50 mu g/mL. In contrast, PDT with 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (TPPS4) requires concentrations of greater than 100 mu g/mL to achieve LD50 Neither 1 nor TPPS4 shows significant photoactivity against the murine T-cell line, MOLT-4, above the dark toxicity. Sensitizer 1 shows no toxicity or side effects in BALB/c mice observed for 30 days following a single intravenous injection of 10 mg (9.1 mu mol)/kg. Distribution studies show that sensitizer 1 accumulates in the tumors of BALB/c mice bearing Cole-26 or EMT-6 tumors with sensitizer concentration roughly doubling as the dosage of 1 increased from 5 to 10 mg/kg. In vivo studies show that PDT with sensitizer 1 at both 3.25 and 10 mg/kg with 135 cm(-2) of 694-nm light is effective against Cola-26 tumors in BALB/c mice.

  DOI：

  10.1021/jm000044i

文献信息

• Synthesis of new tetraphenylporphyrin molecules containing heteroatoms other than nitrogen: II. Tetraphenyl-21-selena-23-thiaporphyrin and tetraphenyl-21,23-diselenaporphyrin
  作者：A. Ulman、J. Manassen、F. Frolow、D. Rabinovich

  DOI：10.1016/s0040-4039(01)85074-7

  日期：——
• One pot synthesis of core modified expanded porphyrins
  作者：Simi K. Pushpan、Jeyaprakash S. Narayanan、Alagar Srinivasan、Sumeet Mahajan、Tavarekere K. Chandrashekar、Raja Roy

  DOI：10.1016/s0040-4039(98)02077-2

  日期：1998.12

  Reaction of various diols with pyrrole in TFA/CH2Cl2 leads co formation of core modified expanded porphyrins.
• Sapphyrin Supramolecules through C−H⋅⋅⋅S and C−H⋅⋅⋅Se Hydrogen Bonds—First Structural Characterization ofmeso- Arylsapphyrins Bearing Heteroatoms
  作者：Seenichamy Jeyaprakash Narayanan、Bashyam Sridevi、Tavarekere K. Chandrashekar、Ashwani Vij、Raja Roy

  DOI：10.1002/(sici)1521-3773(19981231)37:24<3394::aid-anie3394>3.0.co;2-4

  日期：1998.12.31

  An unprecedented coupling reaction of heteroatom-containing tripyrranes leads to the formation of core-modified sapphyrins 1 and 2, which self-assemble in the solid state to form supramolecular ladders. Weak C-H⋅⋅⋅S and C-H⋅⋅⋅Se hydrogen-bonding interactions in addition to C-H⋅⋅⋅N hydrogen bonds are responsible for the observed structures.