3-(2-bromo-benzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-dione | 1233207-72-1

• 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-(2-bromo-benzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-dione
• 英文别名: 3-[(2-Bromophenyl)methyl]-5-[(4-methylsulfonylphenyl)methylidene]-1,3-thiazolidine-2,4-dione；3-[(2-bromophenyl)methyl]-5-[(4-methylsulfonylphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1233207-72-1
• 化学式: C₁₈H₁₄BrNO₄S₂
• 分子量: 452.349
• InChiKey: DKBISPYIRVDTHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-bromo-benzyl-thiazolidine-2,4-dione 、 ethyl 3-(4-methanesulfonyl-phenyl)-2-cyanoacrylate 在 哌啶 作用下， 以 乙醇 为溶剂， 以56%的产率得到3-(2-bromo-benzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands

  摘要：

  Eight new 5-arylidene-3-benzyl-thiazolidine-2,4-diones with halide groups on their benzyl rings were synthesized and assayed in vivo to investigate their anti-inflammatory activities. These compounds showed considerable biological efficacy when compared to rosiglitazone, a potent and well-known agonist of PPAR gamma, which was used as a reference drug. This suggests that the substituted 5-arylidene and 3-benzylidene groups play important roles in the anti-inflammatory properties of this class of compounds. Docking studies with these compounds indicated that they exhibit specific interactions with key residues located in the site of the PPAR gamma structure, which corroborates the hypothesis that these molecules are potential ligands of PPAR gamma. In addition, competition binding assays showed that four of these compounds bound directly to the ligand-binding domain of PPAR gamma, with reduced affinity when compared to rosiglitazone. An important trend was observed between the docking scores and the anti-inflammatory activities of this set of molecules. The analysis of the docking results, which takes into account the hydrophilic and hydrophobic interactions between the ligands and the target, explained why the 3-(2-bromobenzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-dione compound had the best activity and the best docking score. Almost all of the stronger hydrophilic interactions occurred between the substituted 5-arylidene group of this compound and the residues of the binding site. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.045

文献信息

• Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands
  作者：Cleiton Diniz Barros、Angélica Amorim Amato、Tiago Bento de Oliveira、Karime Bicas Rocha Iannini、Anekécia Lauro da Silva、Teresinha Gonçalves da Silva、Elisa Soares Leite、Marcelo Zaldini Hernandes、Maria do Carmo Alves de Lima、Suely Lins Galdino、Francisco de Assis Rocha Neves、Ivan da Rocha Pitta

  DOI：10.1016/j.bmc.2010.04.045

  日期：2010.6

  Eight new 5-arylidene-3-benzyl-thiazolidine-2,4-diones with halide groups on their benzyl rings were synthesized and assayed in vivo to investigate their anti-inflammatory activities. These compounds showed considerable biological efficacy when compared to rosiglitazone, a potent and well-known agonist of PPAR gamma, which was used as a reference drug. This suggests that the substituted 5-arylidene and 3-benzylidene groups play important roles in the anti-inflammatory properties of this class of compounds. Docking studies with these compounds indicated that they exhibit specific interactions with key residues located in the site of the PPAR gamma structure, which corroborates the hypothesis that these molecules are potential ligands of PPAR gamma. In addition, competition binding assays showed that four of these compounds bound directly to the ligand-binding domain of PPAR gamma, with reduced affinity when compared to rosiglitazone. An important trend was observed between the docking scores and the anti-inflammatory activities of this set of molecules. The analysis of the docking results, which takes into account the hydrophilic and hydrophobic interactions between the ligands and the target, explained why the 3-(2-bromobenzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-dione compound had the best activity and the best docking score. Almost all of the stronger hydrophilic interactions occurred between the substituted 5-arylidene group of this compound and the residues of the binding site. (C) 2010 Elsevier Ltd. All rights reserved.