ethyl (Z)-2-(2-naphthalen-1-ylmethylene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo [3,2-a]pyrimidine-6-carboxylate | 1443655-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl (Z)-2-(2-naphthalen-1-ylmethylene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo [3,2-a]pyrimidine-6-carboxylate
• 英文别名: ethyl (2Z)-7-methyl-2-(naphthalen-1-ylmethylidene)-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 1443655-23-9
• 化学式: C₂₇H₂₂N₂O₃S
• 分子量: 454.549
• InChiKey: XQYLJHPJADGVAV-JWGURIENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 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-naphthalen-1-ylmethylene)-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

• 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.