(Z)-N-cyclohexyl-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide | 1266715-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-N-cyclohexyl-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide
• 英文别名: N-cyclohexyl-2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetamide
• CAS: 1266715-57-4
• 化学式: C₁₈H₂₀N₂O₄S
• 分子量: 360.434
• InChiKey: SXJNPXFBRFFSJI-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯-n-环己基-乙酰胺 在 哌啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 0.5h， 生成 (Z)-N-cyclohexyl-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide
  参考文献：
  名称：

  一些新颖的格列酮通过两个碳酰基连接基与甘氨酸，芳香族和脂环族胺部分结合的合成，葡萄糖吸收活性和构效关系

  摘要：

  通过使用适当的合成方案，通过两个碳连接基掺入甘氨酸，芳香族和脂环族胺，设计和制备了三个系列的新型格列酮。化合物是在常规方法和微波方法下合成的。使用分离的大鼠半隔膜评估了二十四种合成化合物中的十九种的体外葡萄糖摄取活性。化合物，6，图9A，图13A，13B，13C，13F和13H显示出显著葡萄糖摄取活性。有关其合成和体外的插图 描述了葡萄糖摄取活性以及结构-活性关系。

  DOI：

  10.1016/j.ejmech.2010.12.019

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.
• Synthesis, glucose uptake activity and structure–activity relationships of some novel glitazones incorporated with glycine, aromatic and alicyclic amine moieties via two carbon acyl linker
  作者：B.R. Prashantha Kumar、Mukesh Soni、S. Santhosh Kumar、Kuldeep Singh、Mohan Patil、R.B. Nasir Baig、Laxmi Adhikary

  DOI：10.1016/j.ejmech.2010.12.019

  日期：2011.3

  Three series of novel glitazones were designed and prepared by using appropriate synthetic schemes to incorporate glycine, aromatic and alicyclic amines via two carbon linker. Compounds were synthesized both under conventional and microwave methods. Nineteen out of twenty four synthesized compounds were evaluated for their in vitro glucose uptake activity using isolated rat hemi-diaphragm. Compounds

  通过使用适当的合成方案，通过两个碳连接基掺入甘氨酸，芳香族和脂环族胺，设计和制备了三个系列的新型格列酮。化合物是在常规方法和微波方法下合成的。使用分离的大鼠半隔膜评估了二十四种合成化合物中的十九种的体外葡萄糖摄取活性。化合物，6，图9A，图13A，13B，13C，13F和13H显示出显著葡萄糖摄取活性。有关其合成和体外的插图 描述了葡萄糖摄取活性以及结构-活性关系。