1,1'-(4,4'-(1,3-phenylenebis(oxy))bis(4,1-phenylene))bis(N'-ethoxycarbonylthiourea) | 1350828-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1'-(4,4'-(1,3-phenylenebis(oxy))bis(4,1-phenylene))bis(N'-ethoxycarbonylthiourea)
• 英文别名: ethyl N-[[4-[3-[4-(ethoxycarbonylcarbamothioylamino)phenoxy]phenoxy]phenyl]carbamothioyl]carbamate
• CAS: 1350828-43-1
• 化学式: C₂₆H₂₆N₄O₆S₂
• 分子量: 554.648
• InChiKey: MARRZTXIKHFASC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,1'-(4,4'-(1,3-phenylenebis(oxy))bis(4,1-phenylene))bis(N'-ethoxycarbonylthiourea) 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 1,1'-(4,4'-(1,3-phenylenebis(oxy))bis(4,1-phenylene))bis(N'-methylguanidine)
  参考文献：
  名称：

  Molecular modeling study and synthesis of novel dicationic flexible triaryl guanidines and imidamides as antiprotozoal agents

  摘要：

  A new series of fourteen dicationic flexible triaryl bis-guanidines 3a,b, bis-N-substituted guanidines 7a,b and 8a,b as well as bis-imidamides 9-12a,b having a 1,3- or 1,4-diphenoxybenzene scaffold backbone were synthesized. The in vitro activity of the novel dications as antiprotozoal agents against Trypanosoma brucei rhodesiense (T.b.r.) and Plasmodium falciparum (P.f.) was assessed. Interestingly, six of the newly synthesized dications viz 3a,b, 7a,b and 8a,b were more active against P.f than the reference drug pentamidine. Also, some of the dications showed moderate antitrypanosomal activity. Thermal melting analysis of the novel dications was performed to determine their ligand-DNA relative binding affinities. Finally, docking of the dications with an AT rich DNA oligonucleotide was executed to understand their binding mode with the minor groove. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.047
• 作为产物：
  描述：

  1,3-二(4-氨苯氧基)苯 、 异硫氰酰甲酸乙酯 以 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到1,1'-(4,4'-(1,3-phenylenebis(oxy))bis(4,1-phenylene))bis(N'-ethoxycarbonylthiourea)
  参考文献：
  名称：

  Molecular modeling study and synthesis of novel dicationic flexible triaryl guanidines and imidamides as antiprotozoal agents

  摘要：

  A new series of fourteen dicationic flexible triaryl bis-guanidines 3a,b, bis-N-substituted guanidines 7a,b and 8a,b as well as bis-imidamides 9-12a,b having a 1,3- or 1,4-diphenoxybenzene scaffold backbone were synthesized. The in vitro activity of the novel dications as antiprotozoal agents against Trypanosoma brucei rhodesiense (T.b.r.) and Plasmodium falciparum (P.f.) was assessed. Interestingly, six of the newly synthesized dications viz 3a,b, 7a,b and 8a,b were more active against P.f than the reference drug pentamidine. Also, some of the dications showed moderate antitrypanosomal activity. Thermal melting analysis of the novel dications was performed to determine their ligand-DNA relative binding affinities. Finally, docking of the dications with an AT rich DNA oligonucleotide was executed to understand their binding mode with the minor groove. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.047

文献信息

• Molecular modeling study and synthesis of novel dicationic flexible triaryl guanidines and imidamides as antiprotozoal agents
  作者：Reem K. Arafa、Tanja Wenzler、Reto Brun、Yun Chai、W. David Wilson

  DOI：10.1016/j.ejmech.2011.09.047

  日期：2011.12

  A new series of fourteen dicationic flexible triaryl bis-guanidines 3a,b, bis-N-substituted guanidines 7a,b and 8a,b as well as bis-imidamides 9-12a,b having a 1,3- or 1,4-diphenoxybenzene scaffold backbone were synthesized. The in vitro activity of the novel dications as antiprotozoal agents against Trypanosoma brucei rhodesiense (T.b.r.) and Plasmodium falciparum (P.f.) was assessed. Interestingly, six of the newly synthesized dications viz 3a,b, 7a,b and 8a,b were more active against P.f than the reference drug pentamidine. Also, some of the dications showed moderate antitrypanosomal activity. Thermal melting analysis of the novel dications was performed to determine their ligand-DNA relative binding affinities. Finally, docking of the dications with an AT rich DNA oligonucleotide was executed to understand their binding mode with the minor groove. (C) 2011 Elsevier Masson SAS. All rights reserved.