N-(3, 5-dichlorophenyl)-2-(4-formylphenoxy)acetamide | 575499-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3, 5-dichlorophenyl)-2-(4-formylphenoxy)acetamide
• 英文别名: N-(3,5-dichlorophenyl)-2-(4-formylphenoxy)acetamide
• CAS: 575499-16-0
• 化学式: C₁₅H₁₁Cl₂NO₃
• 分子量: 324.163
• InChiKey: HFPSMZWUSHRCIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  巴比妥酸 、 N-(3, 5-dichlorophenyl)-2-(4-formylphenoxy)acetamide 以 乙醇 、 水 为溶剂， 以92.1%的产率得到N-(3,5-dichlorophenyl)-2-(4-((2,4,6-trioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide
  参考文献：
  名称：

  Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease

  摘要：

  Forty-four barbituric acid or thiobarbituric acid derivatives were synthesized and evaluated for their effects on adipogenesis of 3T3-L1 adipocytes by measuring the expression of adiponectin in vitro. Four compounds (3a, 30, 3s, 4t) were found to increase the expression of adiponectin and lower the leptin level in 31341 adipocytes at respective concentration of 10 mu M. Among them, 3s showed the most efficacious. Oral administration of 3s effectively reduced body weight, liver weight, and visceral fat and regulated serum levels of biochemical markers in the high-fat/diet-induced Wistar rats. Histopathological evaluation of liver sections by Oil Red O and H&E staining confirmed 3s as a potent, orally active molecule for reducing fat deposition against non-alcoholic fatty liver disease. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.033
• 作为产物：
  描述：

  3,5-二氯苯胺 在 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 N-(3, 5-dichlorophenyl)-2-(4-formylphenoxy)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.
• Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease
  作者：Liang Ma、Shilin Li、Hao Zheng、Jinying Chen、Lin Lin、Xia Ye、Zhizhi Chen、Qinyuan Xu、Tao Chen、Jincheng Yang、Neng Qiu、Guangcheng Wang、Aihua Peng、Yi Ding、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.ejmech.2011.02.033

  日期：2011.6

  Forty-four barbituric acid or thiobarbituric acid derivatives were synthesized and evaluated for their effects on adipogenesis of 3T3-L1 adipocytes by measuring the expression of adiponectin in vitro. Four compounds (3a, 30, 3s, 4t) were found to increase the expression of adiponectin and lower the leptin level in 31341 adipocytes at respective concentration of 10 mu M. Among them, 3s showed the most efficacious. Oral administration of 3s effectively reduced body weight, liver weight, and visceral fat and regulated serum levels of biochemical markers in the high-fat/diet-induced Wistar rats. Histopathological evaluation of liver sections by Oil Red O and H&E staining confirmed 3s as a potent, orally active molecule for reducing fat deposition against non-alcoholic fatty liver disease. (C) 2011 Elsevier Masson SAS. All rights reserved.