(Z)-N-(4-acetylphenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide | 1266715-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-N-(4-acetylphenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide
• 英文别名: N-(4-acetylphenyl)-2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetamide
• CAS: 1266715-46-1
• 化学式: C₂₀H₁₆N₂O₅S
• 分子量: 396.423
• InChiKey: YCFSPTJFSIBBST-YVLHZVERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(4-乙酰基苯)-2-氯乙酰胺 在 potassium carbonate 、 溶剂黄146 、 potassium iodide 、 β-丙氨酸 作用下， 以 丙酮 为溶剂， 反应 28.0h， 生成 (Z)-N-(4-acetylphenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel 5-Benzylidenethiazolidine-2,4-dione Derivatives for the Treatment of Inflammatory Diseases

  摘要：

  Twenty-two compounds based on thiazolidine-2,4-dione moiety were synthesized and evaluated for the inhibitory potency on the production of nitric oxide (NO), inducible nitric oxide synthase (iNOS) activity, and the generation of prostaglandin E-2 (PEG(2)). (Z)-N-(3-Chlorophenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene) methyl) phenoxy) acetamide (3I), superior to the commercial anti-inflammatory drug indomethacin, significantly inhibited iNOS activity (IC50 = 8.66 mu M), iNOS-mediated NO, and cyclooxnenase (COX)-2-derived PGE(2) production (IC50 = 4.16 and 23.55 mu M, respectively) on lipopolysaccharide (LPS)-induced. RAW 264.7 cells. Docking study revealed that 3I was perfectly docking into the active site of murine iNOS and suppressed the expression of iNOS protein as evidenced by Western blot analysis. At the dose of 50 mg/kg, oral administration of 3I possessed protective properties in both carrageenan-induced paw edema and adjuvant-induced arthritis rat models.

  DOI：

  10.1021/jm1011534

文献信息

• Synthesis and Biological Evaluation of Novel 5-Benzylidenethiazolidine-2,4-dione Derivatives for the Treatment of Inflammatory Diseases
  作者：Liang Ma、Caifeng Xie、Yinghua Ma、Juan Liu、Mingli Xiang、Xia Ye、Hao Zheng、Zhizhi Chen、Qinyuan Xu、Tao Chen、Jinying Chen、Jincheng Yang、Neng Qiu、Guangcheng Wang、Xiaolin Liang、Aihua Peng、Shengyong Yang、Yuquan Wei、Lijuan Chen

  DOI：10.1021/jm1011534

  日期：2011.4.14

  Twenty-two compounds based on thiazolidine-2,4-dione moiety were synthesized and evaluated for the inhibitory potency on the production of nitric oxide (NO), inducible nitric oxide synthase (iNOS) activity, and the generation of prostaglandin E-2 (PEG(2)). (Z)-N-(3-Chlorophenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene) methyl) phenoxy) acetamide (3I), superior to the commercial anti-inflammatory drug indomethacin, significantly inhibited iNOS activity (IC50 = 8.66 mu M), iNOS-mediated NO, and cyclooxnenase (COX)-2-derived PGE(2) production (IC50 = 4.16 and 23.55 mu M, respectively) on lipopolysaccharide (LPS)-induced. RAW 264.7 cells. Docking study revealed that 3I was perfectly docking into the active site of murine iNOS and suppressed the expression of iNOS protein as evidenced by Western blot analysis. At the dose of 50 mg/kg, oral administration of 3I possessed protective properties in both carrageenan-induced paw edema and adjuvant-induced arthritis rat models.