4,4'-((1,4-phenylenebis(methylene))bis(oxy))bis(2-hydroxybenzaldehyde) | 1436414-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4'-((1,4-phenylenebis(methylene))bis(oxy))bis(2-hydroxybenzaldehyde)
• CAS: 1436414-54-8
• 化学式: C₂₂H₁₈O₆
• 分子量: 378.381
• InChiKey: HEZSVECSQQCELV-UHFFFAOYSA-N

物化性质

• 沸点：
  602.0±50.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,4'-((1,4-phenylenebis(methylene))bis(oxy))bis(2-hydroxybenzaldehyde) 在 caesium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 1,4-bis[4-(2-acetamidoethylamino)methyl-5-(3-cyanopyridin-5-yl-methoxy)phenoxymethyl]benzene
  参考文献：
  名称：

  Design, Synthesis, Evaluation, and Structural Studies of C₂-Symmetric Small Molecule Inhibitors of Programmed Cell Death-1/Programmed Death-Ligand 1 Protein–Protein Interaction

  摘要：

  A series of C-2-symmetric inhibitors was designed and evaluated for inhibitory activity against the programmed cell death-1/programmed death-ligand 1(PD-1/PD-L1) protein protein interaction (PPI) in a homogenous time-resolved fluorescence (HTRF) assay and PD-1 signaling in cell-based coculture assays. CZ symmetric inhibitors 2a (LH1306) and 2b (LH1307) exhibited ICso values of 25 and 3.0 nM, respectively, in the HTRF assay. While 2a was similar to 3.8-fold more potent than previously reported inhibitor la, 2b could not be differentiated from lb due to their high potency and the limit of our HTRF assay conditions. In one cell-based coculture PD-1 signaling assay, 2a and 2b were 8.2- and 2.8-fold more potent in inhibiting PD-1 signaling than la and lb, respectively. NMR and X-ray cocrystal structural studies provided more structural insights into the interaction between 2b and PD-L1; 2b binds to PD-L1 at the PD-1 binding site and induces the formation of a more symmetrically arranged PD-L1 homodimer than that previously reported for other inhibitors.

  DOI：

  10.1021/acs.jmedchem.9b00795
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 2,4-二羟基苯甲醛 在 potassium hydrogencarbonate 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以12%的产率得到4,4'-((1,4-phenylenebis(methylene))bis(oxy))bis(2-hydroxybenzaldehyde)
  参考文献：
  名称：

  Calixarene and hemicarcerand-like compounds obtained by self-assembly of 3-aminophenylboronic acid and salicylaldehyde derivatives

  摘要：

  One-pot synthesis of calixarene and hemicarcerand like compounds can be modulated by use of mono- or bis-salicylaldehyde derivatives respectively, reacting with 3-aminophenylboronic acid. Thus, the first part of this work is focused on the synthesis of calix-like compounds derived from salicylaldehyde units including different substituents on the aromatic moiety. Seven different calix structures are described and their structural analysis has been carried out by spectroscopic techniques. The second part corresponds to the description of bis-salicylaldehyde derivatives, synthesis and reactivity towards the 3-aminophenylboronic acid leading to the formation of hemicarcerand-like compounds. Aliphatic and aromatic chains were inserted as linkers between the two salicylaldehyde units in order to evaluate the influence on the formation of the hemicarcerands compounds. Both, calixarene and hemicarcerand compounds resulted from condensation reactions, wherein the formation of N-B coordination bonds plays a significant role on the macrocyclization process. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.02.033