3,4,5-trihydroxy-N-[2-oxo-2-[[2-oxo-2-[[2-oxo-2-[[3-[[[2-[[2-[[2-[(3,4,5-trihydroxybenzoyl)amino]acetyl]amino]acetyl]amino]acetyl]amino]methyl]phenyl]methylamino]ethyl]amino]ethyl]amino]ethyl]benzamide | 1037569-96-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,5-trihydroxy-N-[2-oxo-2-[[2-oxo-2-[[2-oxo-2-[[3-[[[2-[[2-[[2-[(3,4,5-trihydroxybenzoyl)amino]acetyl]amino]acetyl]amino]acetyl]amino]methyl]phenyl]methylamino]ethyl]amino]ethyl]amino]ethyl]benzamide
• CAS: 1037569-96-2
• 化学式: C₃₄H₃₈N₈O₁₄
• 分子量: 782.721
• InChiKey: XNWJJOWKXZLDCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  354
• 氢给体数：
  14
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  3,4,5-trimethoxy-N-[2-oxo-2-[[2-oxo-2-[[2-oxo-2-[[3-[[[2-[[2-[[2-[(3,4,5-trimethoxybenzoyl)amino]acetyl]amino]acetyl]amino]acetyl]amino]methyl]phenyl]methylamino]ethyl]amino]ethyl]amino]ethyl]benzamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以48%的产率得到3,4,5-trihydroxy-N-[2-oxo-2-[[2-oxo-2-[[2-oxo-2-[[3-[[[2-[[2-[[2-[(3,4,5-trihydroxybenzoyl)amino]acetyl]amino]acetyl]amino]acetyl]amino]methyl]phenyl]methylamino]ethyl]amino]ethyl]amino]ethyl]benzamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of glycine-based molecular tongs as inhibitors of Aβ1–40 aggregation in vitro

  摘要：

  A series of N-terminus benzamides of glycine-based symmetric peptides, linked to m-xylylenediamine and 3,4'-oxydianiline spacers, were prepared and tested as inhibitors of beta-amyloid peptide A beta(1 - 40) aggregation in vitro. Compounds with good anti-aggregating activity were detected. Polyphenolic amides showed the highest anti-aggregating activity, with IC50 values in the micromolar range. Structure - activity relationships suggested that pi - pi stacking and hydrogen-bonding interactions play a key role in the inhibition of A beta(1 - 40) self-assembly leading to amyloid fibrils. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.052

文献信息

• Design, synthesis, and biological evaluation of glycine-based molecular tongs as inhibitors of Aβ1–40 aggregation in vitro
  作者：Saverio Cellamare、Angela Stefanachi、Diana A. Stolfa、Teodora Basile、Marco Catto、Francesco Campagna、Eddy Sotelo、Pasquale Acquafredda、Angelo Carotti

  DOI：10.1016/j.bmc.2008.03.052

  日期：2008.5

  A series of N-terminus benzamides of glycine-based symmetric peptides, linked to m-xylylenediamine and 3,4'-oxydianiline spacers, were prepared and tested as inhibitors of beta-amyloid peptide A beta(1 - 40) aggregation in vitro. Compounds with good anti-aggregating activity were detected. Polyphenolic amides showed the highest anti-aggregating activity, with IC50 values in the micromolar range. Structure - activity relationships suggested that pi - pi stacking and hydrogen-bonding interactions play a key role in the inhibition of A beta(1 - 40) self-assembly leading to amyloid fibrils. (c) 2008 Elsevier Ltd. All rights reserved.