1,3,5-tris(4-aminobenzamidomethyl)-2,4,6-triethylbenzene

• 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: 1,3,5-tris(4-aminobenzamidomethyl)-2,4,6-triethylbenzene
• 英文别名: 4-amino-N-[[3,5-bis[[(4-aminobenzoyl)amino]methyl]-2,4,6-triethyl-phenyl]methyl]benzamide；4-amino-N-[[3,5-bis[[(4-aminobenzoyl)amino]methyl]-2,4,6-triethylphenyl]methyl]benzamide
• 化学式: C₃₆H₄₂N₆O₃
• 分子量: 606.768
• InChiKey: CAPMPWLTAVCVJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氨基苯甲酸 、 1,3,5-三(氨基甲基)-2,4,6-三乙基苯 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 以21%的产率得到1,3,5-tris(4-aminobenzamidomethyl)-2,4,6-triethylbenzene
  参考文献：
  名称：

  Anti-HIV-1 activity of a tripodal receptor that recognizes mannose oligomers

  摘要：

  The glycoprotein gp120 of the HIV-1 viral envelope has a high content in mannose residues, particularly alpha-1,2-mannose oligomers. Compounds that interact with these high-mannose type glycans may disturb the interaction between gp120 and its (co)receptors and are considered potential anti-HIV agents. Previously, we demonstrated that a tripodal receptor (1), with a central scaffold of 1,3,5-triethylbenzene substituted with three 2,3,4-trihydroxybenzoyl groups, selectively recognizes alpha-1,2-mannose polysaccharides. Here we present additional studies to determine the anti-HIV-1 activity and the mechanism of antiviral activity of this compound. Our studies indicate that 1 shows anti-HIV-1 activity in the low micromolar range and has pronounced gp120 binding and HIV-1 integrase inhibitory capacity. However, gp120 binding rather than integrase inhibition seems to be the primary mechanism of antiviral activity of 1. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.027

文献信息

• Anti-HIV-1 activity of a tripodal receptor that recognizes mannose oligomers
  作者：Eva Rivero-Buceta、Paula Carrero、Elena Casanova、Elisa G. Doyagüez、Andrés Madrona、Ernesto Quesada、María Jesús Peréz-Pérez、Raquel Mateos、Laura Bravo、Leen Mathys、Sam Noppen、Evgeny Kiselev、Christophe Marchand、Yves Pommier、Sandra Liekens、Jan Balzarini、María José Camarasa、Ana San-Félix

  DOI：10.1016/j.ejmech.2015.10.027

  日期：2015.12

  The glycoprotein gp120 of the HIV-1 viral envelope has a high content in mannose residues, particularly alpha-1,2-mannose oligomers. Compounds that interact with these high-mannose type glycans may disturb the interaction between gp120 and its (co)receptors and are considered potential anti-HIV agents. Previously, we demonstrated that a tripodal receptor (1), with a central scaffold of 1,3,5-triethylbenzene substituted with three 2,3,4-trihydroxybenzoyl groups, selectively recognizes alpha-1,2-mannose polysaccharides. Here we present additional studies to determine the anti-HIV-1 activity and the mechanism of antiviral activity of this compound. Our studies indicate that 1 shows anti-HIV-1 activity in the low micromolar range and has pronounced gp120 binding and HIV-1 integrase inhibitory capacity. However, gp120 binding rather than integrase inhibition seems to be the primary mechanism of antiviral activity of 1. (C) 2015 Elsevier Masson SAS. All rights reserved.