4-bis(2-bromoethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin | 40176-58-7

• 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: 4-bis(2-bromoethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin
• 英文别名: 2.4-Di(2-bromethyl)deuteroporphyrindimethylester；Bis-(2-bromethyl)-Porphyrin；3,3'-[7,12-bis-(2-bromo-ethyl)-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-diyl]-bis-propionic acid dimethyl ester
• CAS: 40176-58-7
• 化学式: C₃₆H₄₀Br₂N₄O₄
• 分子量: 752.546
• InChiKey: IGBDGLSYJYIVEA-SHWYJLMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.57
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  109.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-bis(2-bromoethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin 在 氢氧化钾 、 二乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2,4-bis[2-(1-S-1-thio-β-D-galactopyranosyl)ethyl]-6,7-bis-[2-carboxyethyl]-1,3,5,8-tetramethylporphyrin
  参考文献：
  名称：

  Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy

  摘要：

  The aim of this work is the synthesis of a new family of glycosylated porphyrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00255-3
• 作为产物：
  描述：

  protoporphyrin IX 在 甲醇 、 二溴亚砜 、 硫酸 、 potassium carbonate 、 thallium(III) nitrate 作用下， 反应 21.0h， 生成 4-bis(2-bromoethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin
  参考文献：
  名称：

  Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy

  摘要：

  The aim of this work is the synthesis of a new family of glycosylated porphyrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00255-3

文献信息

• Mironov, A. F.; Nizhnik, A. N.; Kozhich, D. T., Journal of general chemistry of the USSR, 1981, vol. 51, # 3, p. 565 - 571
  作者：Mironov, A. F.、Nizhnik, A. N.、Kozhich, D. T.、Kozyrev, A. N.、Evstigneeva, R. P.

  DOI：——

  日期：——