diallyl trimesic acid | 1448710-24-4

• 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: diallyl trimesic acid
• 英文别名: 1,3,5-Benzenetricarboxylic acid diallyl ester；3,5-bis(prop-2-enoxycarbonyl)benzoic acid
• CAS: 1448710-24-4
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: HSZOJAPNLUUZGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯均三酸三烯丙基酯 在 烯丙醇 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到diallyl trimesic acid
  参考文献：
  名称：

  Screening Bicyclic Peptide Libraries for Protein–Protein Interaction Inhibitors: Discovery of a Tumor Necrosis Factor-α Antagonist

  摘要：

  Protein-protein interactions represent a new class of exciting but challenging drug targets, because their large, flat binding sites lack well-defined pockets for small molecules to bind. We report here a methodology for chemical synthesis and screening of large combinatorial libraries of bicyclic peptides displayed on rigid small-molecule scaffolds. With planar trimesic acid as the scaffold, the resulting bicyclic peptides are effective for binding to protein surfaces such as the interfaces of protein-protein interactions. Screening of a bicyclic peptide library against tumor necrosis factor-alpha (TNF alpha) identified a potent antagonist that inhibits the TNF alpha-TNF alpha receptor interaction and protects cells from TNF alpha-induced cell death. Bicyclic peptides of this type may provide a general solution for inhibition of protein-protein interactions.

  DOI：

  10.1021/ja405106u

文献信息

• CHEMICAL SYNTHESIS AND SCREENING OF BICYCLIC PEPTIDE LIBRARIES
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：US20160115202A1

  公开（公告）日：2016-04-28

  Disclosed herein are bicyclic peptide compounds, compositions comprising same, methods for making same, and libraries comprising same. The disclosed compounds, in various aspects, are useful for treating a variety of disorders, including inflammatory disorders, autoimmune disorders, and disorders of uncontrolled cellular proliferation. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本文公开了双环肽化合物、包含它们的组合物、制备它们的方法以及包含它们的库。在各个方面上，所公开的化合物可用于治疗各种疾病，包括炎症性疾病、自身免疫性疾病和细胞增殖失控的疾病。本摘要旨在作为在特定领域进行搜索的扫描工具，并不意味着对本发明的限制。
• [EN] CHEMICAL SYNTHESIS AND SCREENING OF BICYCLIC PEPTIDE LIBRARIES<br/>[FR] SYNTHÈSE CHIMIQUE ET CRIBLAGE DE BANQUES DE PEPTIDES BICYCLIQUES
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2014190257A8

  公开（公告）日：2015-12-10
• US9868767B2
  申请人：——

  公开号：US9868767B2

  公开（公告）日：2018-01-16
• Screening Bicyclic Peptide Libraries for Protein–Protein Interaction Inhibitors: Discovery of a Tumor Necrosis Factor-α Antagonist
  作者：Wenlong Lian、Punit Upadhyaya、Curran A. Rhodes、Yusen Liu、Dehua Pei

  DOI：10.1021/ja405106u

  日期：2013.8.14

  Protein-protein interactions represent a new class of exciting but challenging drug targets, because their large, flat binding sites lack well-defined pockets for small molecules to bind. We report here a methodology for chemical synthesis and screening of large combinatorial libraries of bicyclic peptides displayed on rigid small-molecule scaffolds. With planar trimesic acid as the scaffold, the resulting bicyclic peptides are effective for binding to protein surfaces such as the interfaces of protein-protein interactions. Screening of a bicyclic peptide library against tumor necrosis factor-alpha (TNF alpha) identified a potent antagonist that inhibits the TNF alpha-TNF alpha receptor interaction and protects cells from TNF alpha-induced cell death. Bicyclic peptides of this type may provide a general solution for inhibition of protein-protein interactions.