2-[1-(4-methoxyphenyl)-1-hydroxymethyl]-5-(1-phenyl-1-hydroxymethyl)thiophene | 596104-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[1-(4-methoxyphenyl)-1-hydroxymethyl]-5-(1-phenyl-1-hydroxymethyl)thiophene
• 英文别名: [5-[Hydroxy-(4-methoxyphenyl)methyl]thiophen-2-yl]-phenylmethanol
• CAS: 596104-74-4
• 化学式: C₁₉H₁₈O₃S
• 分子量: 326.416
• InChiKey: KKFKLXIYCYSMOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  77.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-(4-methoxyphenyl)-1-hydroxymethyl]-5-(1-phenyl-1-hydroxymethyl)thiophene 在 三溴化硼 、 四氯苯醌 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 5,10,15-tris-(4-hydroxyphenyl)-20-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：

  苯基(2-噻吩)甲醇 在 4-二甲氨基吡啶 、 正丁基锂 、 四甲基乙二胺 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 2-[1-(4-methoxyphenyl)-1-hydroxymethyl]-5-(1-phenyl-1-hydroxymethyl)thiophene
  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

• Aluminium(iii) porphyrin based axial-bonding type dyads containing thiaporphyrins and expanded thiaporphyrins as axial ligands
  作者：Avijit Ghosh、Dilip Kumar Maity、Mangalampalli Ravikanth

  DOI：10.1039/c2nj40631d

  日期：——

  Four axial-bonding type Al(III) porphyrin based dyads, containing thiaporphyrins with N3S 1 and N2S22 cores and expanded thaiporphyrins with N2S33 and N2S44 cores, were synthesised by treating [(TPP)AlIIIOH] with the corresponding mono-functionalised meso-4-hydroxyphenyl thiaporphyrin or expanded thiaporphyrin building blocks in benzene at refluxing temperature. The stable dyads 1–4 are freely soluble

  四个轴向接合型Al（III）卟啉基对，含有thiaporphyrins用N 3小号1和N 2小号2个2核和扩展thaiporphyrins用N 2小号3 3和N 2小号4 4个芯，分别通过处理[（合成（TPP）Al III OH]与相应的单官能化内消旋-4-羟苯基硫代卟啉或扩展的硫代卟啉结构单元苯在回流温度下。稳定的二元组1-4可自由溶于常见的有机溶剂，并具有质量，1D和2D NMR，吸收，电化学和荧光技术的特征。1D和2D NMR研究明确证实了二元组。吸收和电化学研究表明，二元组中的两个大环之间的相互作用较弱，而二元组中构成的大环大部分保留了其特征性的个体特征。稳态荧光研究表明，二元组1-4中Al（III）卟啉单元的量子产率降低，并引发了单重态-单重态能量从Al（III）卟啉单元转移到N 3 S卟啉单元的可能性。二元组1和dyad 2中的N 2 S 2卟啉单元。通过应用基于密度泛函理论（
• Novel and Rapid Synthetic Routes to A3B- and AB3-Type 21-Thiaporphyrins and Their Use in the Construction of Unsymmetrical Covalent and Non-Covalent Porphyrin Arrays
  作者：Iti Gupta、Neeraj Agarwal、Mangalampalli Ravikanth

  DOI：10.1002/ejoc.200300764

  日期：2004.4

  Novel and very simple methods were developed for the synthesis of 21-thiaporphyrins having both one functional group (A3B) and three functional groups (AB3). These A3B- and AB3-type 21-thiaporphyrin building blocks were used to synthesize both covalently and non-covalently linked unsymmetrical porphyrin arrays containing N3S and N4 porphyrin cores. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  开发了新颖且非常简单的方法来合成具有一个官能团 (A3B) 和三个官能团 (AB3) 的 21-硫卟啉。这些 A3B 和 AB3 型 21-硫卟啉构建块用于合成包含 N3S 和 N4 卟啉核心的共价和非共价连接的不对称卟啉阵列。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Water Soluble, Core-Modified Porphyrins. 3. Synthesis, Photophysical Properties, and in Vitro Studies of Photosensitization, Uptake, and Localization with Carboxylic Acid-Substituted Derivatives
  作者：Youngjae You、Scott L. Gibson、Russell Hilf、Sherry R. Davies、Allan R. Oseroff、Indrajit Roy、Tymish Y. Ohulchanskyy、Earl J. Bergey、Michael R. Detty

  DOI：10.1021/jm030136i

  日期：2003.8.1

  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.