N-(4-acetylphenyl)-3-oxobutanamide | 83999-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetylphenyl)-3-oxobutanamide
• CAS: 83999-28-4
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: MCDZXMSMMJKWRH-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  450.3±30.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-acetylphenyl)-3-oxobutanamide 在 Selectfluor 作用下， 以 PEG-400 为溶剂， 反应 8.0h， 以94%的产率得到N-(4-acetylphenyl)-2-fluoro-3-oxobutanamide
  参考文献：
  名称：

  Catalyst-free and highly selective electrophilic mono-fluorination of acetoacetamides: facile and efficient preparation of 2-fluoroacetoacetamides in PEG-400

  摘要：

  一系列α-单氟乙酰胺在PEG-400中使用工业化Selectfluor作为F+源，在温和条件下被合成。该方法避免了使用碱或金属催化剂，并且在大多数情况下，无论多样性取代基的电子性质如何，都能实现几乎定量的转化。

  DOI：

  10.1039/c2gc16661e
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 1,3,5-三硝基苯 、 N-(4-acetylphenyl)-3-oxobutanamide
  参考文献：
  名称：

  Gnanadoss, Lalitha; Radha, N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 11, p. 1077 - 1081

  摘要：

  DOI：

文献信息

• <p>Virtual Screening and Optimization of Novel mTOR Inhibitors for Radiosensitization of Hepatocellular Carcinoma</p>
  作者：Ying-Qi Feng、Shuang-Xi Gu、Yong-Shou Chen、Xu-Dong Gao、Yi-Xin Ren、Jian-Chao Chen、Yin-Ying Lu、Heng Zhang、Shuang Cao

  DOI：10.2147/dddt.s249156

  日期：——

  thus, mTOR inhibitors have potential as novel radiosensitizers to enhance the efficacy of radiotherapy for HCC. Methods: A lead compound was found based on pharmacophore modeling and molecular docking, and optimized according to the differences between the ATP-binding pockets of mTOR and PI3K. The radiosensitizing effect of the optimized compound ( 2a) was confirmed by colony formation assays and DNA

  背景：放疗对多种肿瘤都有改善作用，但肝细胞癌 (HCC) 对这种治疗不敏感。过活化的哺乳动物雷帕霉素靶蛋白（mTOR）在肝癌对放疗的抵抗中起重要作用；因此，mTOR 抑制剂具有作为新型放射增敏剂的潜力，可增强 HCC 放射治疗的疗效。 方法：基于药效团建模和分子对接发现先导化合物，并根据mTOR和PI3K的ATP结合口袋之间的差异进行优化。优化后化合物的放射增敏作用( 2a) 通过体外集落形成试验和 DNA 双链断裂试验得到证实。描述了该化合物的发现和临床前特征。 结果：鉴定出mTOR中的关键氨基酸残基，构建了精准的虚拟筛选模型。具有 4,7-二氢-[1,2,4]三唑并[1,5-a]嘧啶支架的化合物2a对 mTOR (mTOR IC 50 =7.1 nmol/L (nM)) 具有良好的 126-选择性超过 PI3Kα。此外，2a以剂量依赖性方式显着增强了HCC对体外放射治疗的敏感性。 结论：开发了一类新的选择性
• Synthesis of <i>β</i> -Ketoamide Curcumin Analogs for Anti-Diabetic and AGEs Inhibitory Activities
  作者：Govindharasu Banuppriya、Rajendran Sribalan、Sulthan Alavudeen Rizwan Fathima、Vediappen Padmini

  DOI：10.1002/cbdv.201800105

  日期：2018.8

  Two different series of novel β-ketoamide curcumin analogs enriched in biological activities have been synthesized. The synthesized compounds were screened for their in vitro anti-diabetic and AGEs inhibitory activities and exhibited potent to good anti-diabetic and AGEs inhibitory activities. The molecular docking study was also performed with the α-amylase enzyme.

  已经合成了两个具有丰富生物活性的不同系列的新型β-酮酰胺姜黄素类似物。筛选合成的化合物的体外抗糖尿病和AGEs抑制活性，并表现出对良好的抗糖尿病和AGEs抑制活性的作用。分子对接研究也使用α-淀粉酶进行。
• Gewald synthesis, antitumor profile and molecular modeling of novel 5-acetyl-4-((4-acetylphenyl)amino)-2-aminothiophene-3-carbonitrile scaffolds
  作者：Mohamed E. Khalifa、Wesam M. Algothami

  DOI：10.1016/j.molstruc.2020.127784

  日期：2020.5

  performed depending on the reactivity of the substituents attached to the thiophene nucleus towards various nucleophiles. The chemical structures of the synthesized compounds were elucidated by various spectral analyses. Molecular modeling studies displayed the geometrical structures for the investigated compounds and exhibited that the sulfur and carbon atoms at positions 2 and 4 have positive charges

  摘要 基于使用 Gewald 方法制备新的 5-乙酰基-4-((4-乙酰苯基)氨基)-2-氨基噻吩-3-甲腈 (2)，合成了 2-氨基噻吩衍生物 (2-9) 的新靶点。根据连接到噻吩核的取代基对各种亲核试剂的反应性，进行了几种功能性化学反应。通过各种光谱分析阐明了合成化合物的化学结构。分子模型研究显示了所研究化合物的几何结构，并表明 2 和 4 位的硫和碳原子带正电荷，而 3 和 5 位的硫和碳原子带负电荷，发现它们更具反应性。研究了所研究化合物的潜在生物活性作为抗两种人肿瘤细胞系的抗肿瘤剂，即；肝细胞癌 (HEPG-2) 和乳腺乳腺癌 (MCF-7)。与参考对照药物（多柔比星）相比，发现所有化合物均以不同程度抑制两种人类肿瘤细胞系的生长。实际结果与建模研究非常吻合。
• Electroreductive synthesis of polyfunctionalized pyridin-2-ones from acetoacetanilides and carbon disulfide with oxygen evolution
  作者：Lichun Xu、Zhongxiao Ma、Xi Hu、Xin Zhang、Shulin Gao、Deqiang Liang、Baoling Wang、Weili Li、Yanni Li

  DOI：10.1039/d1ob02379a

  日期：——

  A reductant-free electroreductive synthesis of polyfunctionalized pyridin-2-ones under the combined action of electro/copper/base with O₂ evolution.

  一种无还原剂电还原合成多官能团吡啶-2-酮的方法，在电/铜/碱的共同作用下，并伴随着氧气的释放。
• Microwave-Assisted Synthesis of Diverse Pyrrolo[3,4-<i>c</i>]quinoline-1,3-diones and Their Antibacterial Activities
  作者：Likai Xia、Akber Idhayadhulla、Yong Rok Lee、Sung Hong Kim、Young-Jung Wee

  DOI：10.1021/co500002s

  日期：2014.7.14

  With the aim of developing a general and practical method for library production, a novel and efficient two-phase microwave-assisted cascade reaction between isatins and beta-ketoamides in [Bmim]BF4/toluene was developed for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones. The features of this methodology are, the use of microwave-assisted rapid synthesis, mild reaction conditions, high yields, operational simplicity, facile product separation, and recyclability. Furthermore, the antibacterial activities of the pyrrolo[3,4-c]quinoline-1,3-dione derivatives produced were evaluated against Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Enterobacter aerogenes) and Gram-positive bacteria (Bacillus cereus and Staphylococcus aureus). These derivatives showed antibacterial activities against Gram-positive strains that were at least equivalent to that against Gram-negative strains. Compound 73,5} displayed the most potent antibacterial activity against P. aeruginosa (MIC = 0.5 mu g/mL) and greater activity than standard ampicillin (MIC = 1 mu g/mL). Compound 74,7} exhibited the best inhibitory activity against E. coli and E. aerogenes (MIC = 1 and 0.5 mu g/mL), compared with the standard ampicillin (both MICs = 1 mu g/mL). The synthesized pyrrolo[3,4-c]quinoline-1,3-diones are expected to be widely used as lead compounds for the development of new antibacterial agents.