1,3,5-tris(tert-butylureidomethyl)-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(tert-butylureidomethyl)-2,4,6-triethylbenzene
• 英文别名: 1-[[3,5-Bis[(tert-butylcarbamoylamino)methyl]-2,4,6-triethylphenyl]methyl]-3-tert-butylurea；1-[[3,5-bis[(tert-butylcarbamoylamino)methyl]-2,4,6-triethylphenyl]methyl]-3-tert-butylurea
• 化学式: C₃₀H₅₄N₆O₃
• 分子量: 546.797
• InChiKey: BVCBZFUQBBYNRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  123
• 氢给体数：
  6
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,5-三乙基苯 在 氢溴酸 、 一水合肼 、 zinc dibromide 作用下， 以 乙醇 、 溶剂黄146 、 二甲基亚砜 、 甲苯 为溶剂， 反应 46.0h， 生成 1,3,5-tris(tert-butylureidomethyl)-2,4,6-triethylbenzene
  参考文献：
  名称：

  A New Tripodal Receptor for Molecular Recognition of Monosaccharides. A Paradigm for Assessing Glycoside Binding Affinities and Selectivities by ¹H NMR Spectroscopy

  摘要：

  A new tripodal receptor for the recognition of monosaccharides is described. The prototypical host 1 features a 1,35-substituted 2,4,6-tri ethyl benzene scaffold bearing three convergent H-bonding units. The binding ability of the t-octyl derivative la toward a set of octylglycosides of biologically relevant monosaccharides, including Glc, Gal, Man, and GlcNAc, was investigated by H-1 NMR in CDCl3. A protocol for the correct evaluation of binding affinities was established, which can be generally applied for the recognition of monosaccharides by H-1 NMR spectroscopy. A three-constant equilibrium model, including 1:1 and 2:1 host-guest association and dimerization of the receptor, was ascertained for the interaction of la with all the investigated glycosides. An affinity index, which we defined median binding concentration BC50 in analogy to the IC50 parameter, intended to address the general issue of comparing dimensionally heterogeneous binding data, and a limiting BC500 quantity describing intrinsic binding affinities were developed for evaluating the results. BC500 values for la range from 1 to 6 mM, indicating an intrinsic binding affinity in the millimolar range and a selectivity factor of 5 toward the investigated glycosides. The treatment has been extended to include any generic host-guest system involved in single or multiple binding equilibria.

  DOI：

  10.1021/ja045813s

文献信息

• A New Tripodal Receptor for Molecular Recognition of Monosaccharides. A Paradigm for Assessing Glycoside Binding Affinities and Selectivities by ¹H NMR Spectroscopy
  作者：Alberto Vacca、Cristina Nativi、Martina Cacciarini、Roberto Pergoli、Stefano Roelens

  DOI：10.1021/ja045813s

  日期：2004.12.1

  A new tripodal receptor for the recognition of monosaccharides is described. The prototypical host 1 features a 1,35-substituted 2,4,6-tri ethyl benzene scaffold bearing three convergent H-bonding units. The binding ability of the t-octyl derivative la toward a set of octylglycosides of biologically relevant monosaccharides, including Glc, Gal, Man, and GlcNAc, was investigated by H-1 NMR in CDCl3. A protocol for the correct evaluation of binding affinities was established, which can be generally applied for the recognition of monosaccharides by H-1 NMR spectroscopy. A three-constant equilibrium model, including 1:1 and 2:1 host-guest association and dimerization of the receptor, was ascertained for the interaction of la with all the investigated glycosides. An affinity index, which we defined median binding concentration BC50 in analogy to the IC50 parameter, intended to address the general issue of comparing dimensionally heterogeneous binding data, and a limiting BC500 quantity describing intrinsic binding affinities were developed for evaluating the results. BC500 values for la range from 1 to 6 mM, indicating an intrinsic binding affinity in the millimolar range and a selectivity factor of 5 toward the investigated glycosides. The treatment has been extended to include any generic host-guest system involved in single or multiple binding equilibria.