ethyl (Z)-2-(2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate | 1443655-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl (Z)-2-(2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
• 英文别名: ethyl (2Z)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 1443655-22-8
• 化学式: C₂₄H₂₂N₂O₅S
• 分子量: 450.515
• InChiKey: KABZUQZQDJDIKE-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 在 吡啶 、 氨基磺酸 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 ethyl (Z)-2-(2-hydroxy-3-methoxybenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents

  摘要：

  The modulation of pro-inflammatory cytokines provides a target for controlling inflammatory diseases and attracts much attention in current anti-inflammatory drug development. Here, four series of thiazolidinone derivatives were synthesized and screened for anti-inflammatory activities. A majority of these compounds showed excellent inhibition on the expression of TNF-alpha and IL-6 in LPS-stimulated macrophages. Discussions are given regarding the structure activity relationships. Compounds 12d and 12h inhibited LPS-induced TNF-alpha and IL-6 release in a dose-dependent manner. Furthermore, 12d exhibited a significant protection against LPS-induced septic death in mouse model. Together, these data present a series of new thiazolidinones with potential therapeutic effects in acute inflammatory diseases and they could be important leads in the continuing anti-inflammatory drug research. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.010

文献信息

• (2-Hydroxy-3-Methoxybenzylidene)thiazolo[3,2-a]pyrimidines: Synthesis, Self-Assembly in the Crystalline Phase and Cytotoxic Activity
  作者：Artem S. Agarkov、Anna A. Nefedova、Elina R. Gabitova、Dilyara O. Mingazhetdinova、Alexander S. Ovsyannikov、Daut R. Islamov、Syumbelya K. Amerhanova、Anna P. Lyubina、Alexandra D. Voloshina、Igor A. Litvinov、Svetlana E. Solovieva、Igor S. Antipin

  DOI：10.3390/ijms24032084

  日期：——

  A series of new 2-hydroxy-3-methoxybenzylidenethiazolo[3,2-a]pyrimidines with different aryl substituents at the 5 position are synthesized and characterized by 1H/ 13C NMR and IR-spectroscopy and mass-spectrometry, as well as single crystal X-ray diffraction (SCXRD). It was demonstrated that the type of hydrogen bonding can play a key role in the chiral discrimination of these compounds in the crystalline

  合成了一系列在 5 位具有不同芳基取代基的新型 2-羟基-3-甲氧基亚苄基噻唑并 [3,2-a] 嘧啶，并通过 1H/ 13C 核磁共振、红外光谱和质谱以及单晶表征X 射线衍射 (SCXRD)。事实证明，氢键的类型可以在结晶相中这些化合物的手性区分中发挥关键作用。OH...N 型氢键导致一维超分子异手性链或在形成纯手性链的情况下聚集结晶。OH...O 型氢键产生外消旋二聚体，它们以平行或成角度的二聚体排列方式填充到二维超分子层中。N...Br 或 O...Br 类型的卤素键合为结晶相中的超分子自组装带来了新的基序：形成一维超分子纯手性链而不是二维超分子层。进行了体外对多种肿瘤细胞的细胞毒性研究。结果发现，在 C5 碳原子上具有 3-硝基苯基取代基的 2-羟基-3-甲氧基亚苄基噻唑并 [3,2-a] 嘧啶显示出对 M-HeLa（宫颈腺癌）的高效率和对正常肝细胞的低细胞毒性。
• Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents
  作者：Jie Hu、Yi Wang、Xiaoyan Wei、Xixi Wu、Gaozhi Chen、Gaozhong Cao、Xueqian Shen、Xiuhua Zhang、Qinqin Tang、Guang Liang、Xiaokun Li

  DOI：10.1016/j.ejmech.2013.04.010

  日期：2013.6

  The modulation of pro-inflammatory cytokines provides a target for controlling inflammatory diseases and attracts much attention in current anti-inflammatory drug development. Here, four series of thiazolidinone derivatives were synthesized and screened for anti-inflammatory activities. A majority of these compounds showed excellent inhibition on the expression of TNF-alpha and IL-6 in LPS-stimulated macrophages. Discussions are given regarding the structure activity relationships. Compounds 12d and 12h inhibited LPS-induced TNF-alpha and IL-6 release in a dose-dependent manner. Furthermore, 12d exhibited a significant protection against LPS-induced septic death in mouse model. Together, these data present a series of new thiazolidinones with potential therapeutic effects in acute inflammatory diseases and they could be important leads in the continuing anti-inflammatory drug research. (C) 2013 Elsevier Masson SAS. All rights reserved.