2-(3''-Ethylsulfanyl-biphenyl-4-yl)-propionic 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: 2-(3''-Ethylsulfanyl-biphenyl-4-yl)-propionic acid
• 英文别名: 2-[4-(3-ethylsulfanylphenyl)phenyl]propanoic acid
• 化学式: C₁₇H₁₈O₂S
• 分子量: 286.395
• InChiKey: QGKUCOODYMVNGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-溴苯基)丙酸甲酯 在 sodium hydroxide 、 正丁基锂 、 tris(dibenzylideneacetone)dipalladium (0) 、 硼酸三异丙酯 、 sodium carbonate 、 三苯基膦 作用下， 生成 2-(3''-Ethylsulfanyl-biphenyl-4-yl)-propionic acid
  参考文献：
  名称：

  Structure-based design of COX-2 selectivity into flurbiprofen

  摘要：

  Comparative computer modeling of the X-ray crystal structures of cyclooxygenase isoforms COX-1 and COX-2 has led to the design of COX-2 selectivity into the nonselective inhibitor flurbiprofen. The COX-2 modeling was based on a postulated binding mode for flurbiprofen and took advantage of a small alcove in the COX-2 active site created by different positions of the Leu384 sidechain between COX-I and COX-2. The design hypothesis was tested by synthesis and biological assay of a series of flurbiprofen analogs, culminating in the discovery of several inhibitors having up to 78-fold selectivity for COX-2 over COX-1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00717-3

文献信息

• Structure-based design of COX-2 selectivity into flurbiprofen
  作者：Christopher I. Bayly、W.Cameron Black、Serge Léger、Nathalie Ouimet、Marc Ouellet、M.David Percival

  DOI：10.1016/s0960-894x(98)00717-3

  日期：1999.2

  Comparative computer modeling of the X-ray crystal structures of cyclooxygenase isoforms COX-1 and COX-2 has led to the design of COX-2 selectivity into the nonselective inhibitor flurbiprofen. The COX-2 modeling was based on a postulated binding mode for flurbiprofen and took advantage of a small alcove in the COX-2 active site created by different positions of the Leu384 sidechain between COX-I and COX-2. The design hypothesis was tested by synthesis and biological assay of a series of flurbiprofen analogs, culminating in the discovery of several inhibitors having up to 78-fold selectivity for COX-2 over COX-1. (C) 1999 Elsevier Science Ltd. All rights reserved.