meso-tetrakis[4-(3-bromopropoxy)phenyl]porphyrin | 88367-43-5

• 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: meso-tetrakis[4-(3-bromopropoxy)phenyl]porphyrin
• 英文别名: 5,10,15,20-tetrakis<4-(3-bromopropoxy)phenyl>porphyrin；5,10,15,20-tetra-(4-bromopropoxyphenyl)porphyrin；5,10,15,20-tetrakis[4-(3-bromopropoxy)phenyl]porphyrin
• CAS: 88367-43-5
• 化学式: C₅₆H₅₀Br₄N₄O₄
• 分子量: 1162.65
• InChiKey: JWSYCSHRWHGXAS-YFLSTINXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.98
• 重原子数：
  68.0
• 可旋转键数：
  20.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  94.28
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  meso-tetrakis[4-(3-bromopropoxy)phenyl]porphyrin 、 nickel diacetate 以 甲苯 为溶剂， 以80%的产率得到meso-tetrakis[4-(3-bromopropoxy)phenyl]porphyrin nickel
  参考文献：
  名称：

  Study on the interaction of new water-soluble porphyrin with DNA

  摘要：

  A porphyrin meso-tetrakis{[4-(1-pyridyl)propoxy]phenyl}porphyrin (TPyPP) and its Ni complex (TPyPP(Ni)) have been synthesized and characterized by H-1 NMR, UV-vis spectra. The interaction of two porphyrins with calf thymus-DNA (CT-DNA) has been explored by UV-vis, fluorescence and circular dichroic spectroscopy and viscosity measurements. The results suggest that these porphyrins can bind to DNA by the same binding mode. TPyPP outside binds by self-stack with DNA both at low drug load r (=[porphyrin]/[DNA]) and high drug load. Though TPyPP(Ni) has center metal nickel, binding mode with DNA has little difference compared with TPyPP, dominating out-binding mode with different direction along DNA. The binding constants of the TPyPP and TPyPP(Ni) to DNA were 4.65 x 10(5) M-1 and 3.2 x 10(5) M-1, respectively. A colored precipitate was found after time in two porphyrin's viscosity measurement. The reasonable interpretation is the porphyrins with alkyl connected N-position of pyridine can strongly interact with the anionic phosphates of DNA and lead to hydrophobic complex. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2004.08.009
• 作为产物：
  描述：

  5,10,15,20-tetrakis(4-methoxyphenyl)-21,22-dihydroporphyrin 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.0h， 生成 meso-tetrakis[4-(3-bromopropoxy)phenyl]porphyrin
  参考文献：
  名称：

  Milgrom, Lionel R., Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2535 - 2539

  摘要：

  DOI：

文献信息

• Terpyridine-containing porphyrin and coordination assembly with fullerene-based pyridine for enhanced electrocatalytic oxygen evolution and photocurrent response
  作者：Zhen-Yi Wu、Li-Jing Huang、Rui Zhong

  DOI：10.1016/j.poly.2020.114818

  日期：2021.1
• DNA Interactions with Porphyrins Bearing Ammonium Side Chains
  作者：Hans-Joerg Schneider、Manxue Wang

  DOI：10.1021/jo00103a047

  日期：1994.12

  Eleven new porphyrins bearing either tertiary amine or ammonium groups with different spacers in the meso position have been synthesized. Five of them were water-soluble enough for DNA binding studies. UV/vis measurements of some derivatives as a function of pH quantifies the porphyrin core protonation postulated recently by Marzilli et al. with an uptake of two protons and pK values of 6.0 or 6.4, respectively. The porphyrins as well as their Cu(II) or Zn(II) derivatives decrease the viscosity of ds(CT) DNA slightly and increase the melting point of DNA by only up to 1.7 degrees C at DNA base pair/ligand ratios of 40. DNA causes either a red shift (less than or equal to 6 nm) or a blue shift (greater than or equal to-7 nm) of the Soret bands. These results as well as the observed small hypochromicities show that all new porphyrins interact with DNA without intercalation. However, their affinity in comparison with other macrocycles bearing four positive charges is, based on ethidium bromide assays with C-50 values of 7 x 10(-8) to 2 x 10(-7) M relatively high and points to groove binding contributions by other than electrostatic forces.
• Study on the inclusion behavior between meso-tetrakis[4-(3-pyridiniumpropoxy)phenyl]prophyrin tetrakisbromide and β-cyclodextrin derivatives in aqueous solution
  作者：Wen-Ge Qiu、Zong-Feng Li、Guang-Mei Bai、Sheng-Nan Meng、Hong-Xing Dai、Hong He

  DOI：10.1016/j.saa.2006.06.006

  日期：2007.4

  The interaction of a cationic water-soluble porphyrin, 5,10,15,20-tetrakisi[4-(3-pyridiniumpropoxy)phenyl]prophyrin tetrakisbromide (TPPOC3Py), with beta-CD and HP-beta-CD in aqueous solution has been studied by UV-vis, H-1 NMR, 2D-NOESY and MALDI-TOF MS, and it reveals that a stable 1:1 inclusion complex between TPPOC3Py and HP-beta-CD or beta-CD has formed, in which one of the meso substituents of porphyrin ring has deeply penetrated through the cavity of HP-beta-CD from secondary face. The inclusion constants of the complexes of TPPOC3Py-beta-CD and TPPOC3Py-HP-beta-CD are (1.6 +/- 0.2) x 10(3) M-1 and (8.9 +/- 0.4) x 10(4) M-1, respectively. (c) 2006 Published by Elsevier B.V.