N-(4-acetylphenyl)-2-(4-formylphenoxy)acetamide | 331962-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetylphenyl)-2-(4-formylphenoxy)acetamide
• CAS: 331962-59-5
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: LARQZOGSRSUNGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  巴比妥酸 、 N-(4-acetylphenyl)-2-(4-formylphenoxy)acetamide 以 乙醇 、 水 为溶剂， 以97.5%的产率得到N-(4-acetylphenyl)-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：

  4-氨基苯乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 28.0h， 生成 N-(4-acetylphenyl)-2-(4-formylphenoxy)acetamide
  参考文献：
  名称：

  3-甲基-5-氧代-4,5-二氢-1H-吡唑-苯磺酰胺衍生物的芳基延伸：作为肿瘤相关碳酸酐酶抑制剂的合成、计算模拟和生物学评价

  摘要：

  据报道，几种吡唑-苯磺酰胺可作为人类碳酸酐酶抑制剂。在这项研究工作中，基于尾部方法设计，报道了亚芳基扩展的 5-氧代-吡唑苯磺酰胺 ( 4a-i )、( 8a-d ) 和 ( 10a-e ) 的设计。除了报道的合成程序和通过不同分析程序的确认之外，还采用 DFT 研究来确认合成化合物的Z构象异构体。对四种不同的人碳酸酐酶进行了体外生物学测定，并根据结果阐述了SAR研究并讨论了选择性指标。化合物4g和8a在目标化合物中表现出最好的抑制活性，其值为 (hCAIX: K I = 71.2 nM, hCAXII: K I = 22.5 nM)，(hCAIX: K I = 34.3 nM, hCAXII: K I = 74.3 nM) ;分别。在常氧和低氧条件下，对两种具有 hCA 同种型表达性质的不同癌细胞系进行细胞测定。与常氧条件下的参考药物阿霉素（IC 50 = 4.34 µM）相比，化合物4g对

  DOI：

  10.1016/j.bioorg.2023.106492

文献信息

• Synthesis of novel 1-alkyl-8-substituted-3-(3-methoxypropyl) xanthines as putative A2B receptor antagonists
  作者：María Isabel Nieto、María Carmen Balo、José Brea、Olga Caamaño、María Isabel Cadavid、Franco Fernández、Xerardo García Mera、Carmen López、José Enrique Rodríguez-Borges

  DOI：10.1016/j.bmc.2009.03.029

  日期：2009.5

  In order to identify a high-affinity, selective antagonist for the A(2B) subtype adenosine receptor, more than 40 1,8-disubstituted-3-(3-methoxypropyl) xanthines were prepared and evaluated for their binding affinity at recombinant human adenosine receptors, mainly of the A(2A) and A(2B) subtypes. Some of the 1-ethyl-3-(3-methoxypropyl)-8-aryl substituted derivatives 15(a-m) showed moderate-to-high affinity at human A(2B) receptors, with compound 15d showing A(2B) selectivity over the other A receptors assayed (A(1), A(2A), A(3)) of 34-fold or over. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Arylidine extensions of 3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-benzenesulfonamide derivatives: Synthesis, computational simulations and biological evaluation as tumor-associated carbonic anhydrase inhibitors
  作者：Heba M. Metwally、Heba Abdelrasheed Allam、Fady Baselious、Alessandro Bonardi、Emad M. Seif、Shaimaa A. Moussa、Ehab Abdel-Latif、Claudiu T. Supuran、Hany S. Ibrahim

  DOI：10.1016/j.bioorg.2023.106492

  日期：2023.6

  of the synthesized compounds. In vitro biological assay against four different human carbonic anhydrases took place and based on the results, SAR study was illustrated and selectivity indexes were discussed. Compounds 4g and 8a exhibited the best inhibitory activity among the target compounds with values (hCAIX: KI = 71.2 nM, hCAXII: KI = 22.5 nM), (hCAIX: KI = 34.3 nM, hCAXII: KI = 74.3 nM); respectively

  据报道，几种吡唑-苯磺酰胺可作为人类碳酸酐酶抑制剂。在这项研究工作中，基于尾部方法设计，报道了亚芳基扩展的 5-氧代-吡唑苯磺酰胺 ( 4a-i )、( 8a-d ) 和 ( 10a-e ) 的设计。除了报道的合成程序和通过不同分析程序的确认之外，还采用 DFT 研究来确认合成化合物的Z构象异构体。对四种不同的人碳酸酐酶进行了体外生物学测定，并根据结果阐述了SAR研究并讨论了选择性指标。化合物4g和8a在目标化合物中表现出最好的抑制活性，其值为 (hCAIX: K I = 71.2 nM, hCAXII: K I = 22.5 nM)，(hCAIX: K I = 34.3 nM, hCAXII: K I = 74.3 nM) ;分别。在常氧和低氧条件下，对两种具有 hCA 同种型表达性质的不同癌细胞系进行细胞测定。与常氧条件下的参考药物阿霉素（IC 50 = 4.34 µM）相比，化合物4g对