3-乙酰基-6-氯-1-甲基-4-苯基喹啉-2(1H)-酮 | 479076-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 3-乙酰基-6-氯-1-甲基-4-苯基喹啉-2(1H)-酮
• 英文名称: 3-acetyl-1-methyl-6-chloro-4-phenylquinolin-2(1H)-one
• 英文别名: 3-acetyl-6-chloro-1-methyl-4-phenylquinolin-2(1H)-one；3-acetyl-6-chloro-1-methyl-4-phenylquinolin-2-one
• CAS: 479076-89-6
• 化学式: C₁₈H₁₄ClNO₂
• 分子量: 311.768
• InChiKey: KECXYNJOPPYALX-UHFFFAOYSA-N

物化性质

• 沸点：
  472.4±45.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)
• 溶解度：
  38.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙酰基-6-氯-1-甲基-4-苯基喹啉-2(1H)-酮 、 N-甲硫脲 在 碘 作用下， 以82.3%的产率得到1-methyl-3-[2-(methylamino)thiazol-4-yl]-4-phenyl-6-chloroquinolin-2(1H)-one
  参考文献：
  名称：

  Molecular Iodine as a Versatile Reagent for the Synthesis of Thiazoloquinoline—A Potential Antibacterial Agent

  摘要：

  A series of 3-(2-aminothiazol-4-yl) quinolin-2[1H]-ones 3 was prepared by neat reaction of quinolin-2[1H]-ones 1 with thioureas 2 in the presence of molecular iodine. The synthesized compounds were evaluated for their in vitro antimicrobial activities against Escherichia coli, Paedococcus sp., Lactobacillus, Yersinia enterocolitica, and Staphylococcus aureus. The green chemical approach for the synthesis of thiazoloquinolinone 3 was performed under neat conditions using molecular iodine as catalyst as well as reaction medium.

  DOI：

  10.1080/10426507.2010.503209
• 作为产物：
  描述：

  2-氨基-5-氯二苯甲酮 在 Amberlite Na sr1L 作用下， 反应 0.14h， 生成 3-乙酰基-6-氯-1-甲基-4-苯基喹啉-2(1H)-酮
  参考文献：
  名称：

  Solvent-free synthesis and antibacterial studies of some quinolinones

  摘要：

  Solvent-free, microwave-induced condensation of 2-aminoaryl alkyl ketones and ethyl 3-oxobutanoate in the presence of amberlite Na sr1L gave quinolinones in high yield when compared to other catalysts. Further, N-alkylation of the quinolinones was carried out effectively with various halides using amberlite Na sr1L. An N-alkylated quinolinone exhibited enhanced activities against B. subtilis, E. coli, and P. aeruginosa, similar to standard drug ampicillin. Two compounds showed effective activity against S. aureus, and one resulted in moderate activity against E. coli.

  DOI：

  10.1007/s00706-011-0608-1

文献信息

• Synthesis and SAR Studies of Dual AKT/NF-κB Inhibitors Against Melanoma
  作者：Elisa Barile、Surya K. De、Yongmei Feng、Vida Chen、Li Yang、Ze'ev Ronai、Maurizio Pellecchia

  DOI：10.1111/cbdd.12177

  日期：2013.11

  The protein Kinase B alpha (AKT) and nuclear factor kappa‐light‐chain‐enhancer of activated B cells (NF‐κB) pathways are central regulators of cellular signaling events at the basis of tumor development and progression. Both pathways are often up‐regulated in different tumor types including melanoma. We recently reported the identification of compound 1 (BI‐69A11) as inhibitor of the AKT and the NF‐κB pathways. Here, we describe SAR studies that led to novel fluorinated derivatives with increased cellular potency, reflected in efficient inhibition of AKT and IKKs. Selected compounds demonstrated effective toxicity on melanoma, breast, and prostate cell lines. Finally, a representative derivative showed promising efficacy in an in vivo melanoma xenograft model.
• Solvent-free synthesis and antibacterial studies of some quinolinones
  作者：Radhakrishnan Subashini、Fazlur-Rahman Nawaz Khan

  DOI：10.1007/s00706-011-0608-1

  日期：2012.3

  Solvent-free, microwave-induced condensation of 2-aminoaryl alkyl ketones and ethyl 3-oxobutanoate in the presence of amberlite Na sr1L gave quinolinones in high yield when compared to other catalysts. Further, N-alkylation of the quinolinones was carried out effectively with various halides using amberlite Na sr1L. An N-alkylated quinolinone exhibited enhanced activities against B. subtilis, E. coli, and P. aeruginosa, similar to standard drug ampicillin. Two compounds showed effective activity against S. aureus, and one resulted in moderate activity against E. coli.
• Molecular Iodine as a Versatile Reagent for the Synthesis of Thiazoloquinoline—A Potential Antibacterial Agent
  作者：R. Subashini、F. Nawaz Khan

  DOI：10.1080/10426507.2010.503209

  日期：2011.2.28

  A series of 3-(2-aminothiazol-4-yl) quinolin-2[1H]-ones 3 was prepared by neat reaction of quinolin-2[1H]-ones 1 with thioureas 2 in the presence of molecular iodine. The synthesized compounds were evaluated for their in vitro antimicrobial activities against Escherichia coli, Paedococcus sp., Lactobacillus, Yersinia enterocolitica, and Staphylococcus aureus. The green chemical approach for the synthesis of thiazoloquinolinone 3 was performed under neat conditions using molecular iodine as catalyst as well as reaction medium.