3-(3-chlorobenzyl)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione | 1233207-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-chlorobenzyl)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione
• 英文别名: 3-[(3-chlorophenyl)methyl]-5-[(4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1233207-71-0
• 化学式: C₁₈H₁₄ClNO₃S
• 分子量: 359.833
• InChiKey: LKRZCPJVTYCIQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-chloro-benzyl-thiazolidine-2,4-dione 、 ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate 在 哌啶 作用下， 以 乙醇 为溶剂， 以72%的产率得到3-(3-chlorobenzyl)-5-(4-methoxybenzylidene)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

• 2,4-Thiazolidinedione as Precursor to the Synthesis of Compounds with Anti-glioma Activities in C6 and GL261 Cells
  作者：Alana de Vasconcelos、Ana Júlia Zulian Boeira、Bruna Bento Drawanz、Nathalia Stark Pedra、Natália Pontes Bona、Francieli Moro Stefanello、Wilson Cunico

  DOI：10.2174/1573406416666200403075826

  日期：2021.7

  cytotoxic to both glioblastoma cell lines without being toxic to the astrocyte primary cell line at 100 μM, thus demonstrating a selective activity. Compounds 4CI and 4DI showed the best results in the C6 cells: IC50 of 28.51 μM and 54.26 μM, respectively. Conclusion: The compounds were not cytotoxic in astrocyte culture, demonstrating selectivity for malignant cells. Changes in both rings are important

  背景：噻唑烷二酮 (TZD) 是一类重要的杂环化合物，具有多种生物活性，包括抗癌活性。胶质瘤是最常见的原发性脑肿瘤之一，它是导致原发性脑肿瘤死亡的主要原因。在目前的工作中，2,4-噻唑烷二酮是通过多组分微波一锅法合成的。使用大鼠 (C6) 和小鼠 (GL261) 胶质母细胞瘤细胞系和星形胶质细胞的原代培养物在体外分析了化合物的细胞毒性。 目的：本研究旨在合成和表征 2,4-噻唑烷二酮并评估其抗肿瘤活性。 方法：TZDs 由三种成分合成：2,4-噻唑烷二酮、芳烃醛和芳基氯。反应在微波内进行，并使用薄层色谱 (TLC) 进行监测。使用气相色谱-质谱联用 (CG-MS) 和氢 ( 1 H-NMR) 和碳核磁共振波谱 ( 13核磁共振）。使用 3-(4,5-二甲基)-2,5-二苯基溴化四唑 (MTT) 还原试验分析抗肿瘤活性，其中在星形胶质细胞的原代培养物以及暴露于合成的化合物。在 100 μM