3-(biphenyl-4-ylsulfonamido)propanoic acid

• 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: 3-(biphenyl-4-ylsulfonamido)propanoic acid
• 英文别名: 3-(biphenyl-4-sulfonylamino)-propionic acid；3-[(4-Phenylphenyl)sulfonylamino]propanoic acid
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: QRKMJDDJXOFJLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(biphenyl-4-ylsulfonamido)propanoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-(biphenyl-4-ylsulfonamido)-N-hydroxypropanamide
  参考文献：
  名称：

  Synthesis, experimental evaluation and molecular modelling of hydroxamate derivatives as zinc metalloproteinase inhibitors

  摘要：

  Enzymes of the M4 family of zinc-metalloproteinases are virulence factors secreted from gram-positive or gram-negative bacteria, and putative drug targets in the treatment of bacterial infections. In order to have a therapeutic value such inhibitors should not interfere with endogenous zinc-metalloproteinases. In the present study we have synthesised a series of hydroxamate derivatives and validated the compounds as inhibitors of the M4 enzymes thermolysin and pseudolysin, and the endogenous metalloproteinases ADAM-17, MMP-2 and MMP-9 using experimental binding studies and molecular modelling. In general, the compounds are stronger inhibitors of the MMPs than of the M4 enzymes, however, an interesting exception is LM2. The compounds bound stronger to pseudolysin than to thermolysin, and the molecular modelling studies showed that occupation of the S-2' subpocket by an aromatic group is favourable for strong interactions with pseudolysin. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.019
• 作为产物：
  描述：

  对联苯磺酰氯 、 β-丙氨酸 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以70%的产率得到3-(biphenyl-4-ylsulfonamido)propanoic acid
  参考文献：
  名称：

  Synthesis, experimental evaluation and molecular modelling of hydroxamate derivatives as zinc metalloproteinase inhibitors

  摘要：

  Enzymes of the M4 family of zinc-metalloproteinases are virulence factors secreted from gram-positive or gram-negative bacteria, and putative drug targets in the treatment of bacterial infections. In order to have a therapeutic value such inhibitors should not interfere with endogenous zinc-metalloproteinases. In the present study we have synthesised a series of hydroxamate derivatives and validated the compounds as inhibitors of the M4 enzymes thermolysin and pseudolysin, and the endogenous metalloproteinases ADAM-17, MMP-2 and MMP-9 using experimental binding studies and molecular modelling. In general, the compounds are stronger inhibitors of the MMPs than of the M4 enzymes, however, an interesting exception is LM2. The compounds bound stronger to pseudolysin than to thermolysin, and the molecular modelling studies showed that occupation of the S-2' subpocket by an aromatic group is favourable for strong interactions with pseudolysin. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.019

文献信息

• In silico identification, design and synthesis of novel piperazine-based antiviral agents targeting the hepatitis C virus helicase
  作者：Marcella Bassetto、Pieter Leyssen、Johan Neyts、Mark M. Yerukhimovich、David N. Frick、Matthew Courtney-Smith、Andrea Brancale

  DOI：10.1016/j.ejmech.2016.10.043

  日期：2017.1

  A structure-based virtual screening of commercial compounds was carried out on the HCV NS3 helicase structure, with the aim to identify novel inhibitors of HCV replication. Among a selection of 13 commercial structures, one compound was found to inhibit the subgenomic HCV replicon in the low micromolar range. Different series of new piperazine-based analogues were designed and synthesised, and among them, several novel structures exhibited antiviral activity in the HCV replicon assay. Some of the new compounds were also found to inhibit HCV NS3 helicase function in vitro, and one directly bound NS3 with a dissociation constant of 570 +/- 270 nM. (C) 2016 Elsevier Masson SAS. All rights reserved.
• NOVEL INTEGRIN RECEPTOR ANTAGONISTS
  申请人：Du Pont Pharmaceuticals Company

  公开号：EP0944619A1

  公开（公告）日：1999-09-29
• SIMULTANEOUS IMAGING OF CARDIAC PERFUSION AND A VITRONECTIN RECEPTOR TARGETED IMAGING AGENT
  申请人：Bristol-Myers Squibb Pharma Company

  公开号：EP1423152A2

  公开（公告）日：2004-06-02
• EP1423152A4
  申请人：——

  公开号：EP1423152A4

  公开（公告）日：2006-12-27
• Modified tumor necrosis factor-alpha converting enzyme and methods of use thereof
  申请人：Beyer M. Brian

  公开号：US20070148669A1

  公开（公告）日：2007-06-28

  The present invention discloses a modified tumor necrosis factor-alpha converting enzyme (TACE) catalytic domain, that unlike the native TACE catalytic domain, is stable at high protein concentrations. The present invention further discloses methods for generating crystals of the modified TACE protein in protein-ligand complexes with a number of inhibitors. In addition, the present invention discloses methods of using the proteins, crystals and/or three-dimensional structures obtained to identify compounds that can modulate the enzymatic activity of TACE.