N(1H)-7-(1'-naphthoylamino)-4-methylquinolin-2(1H)-one | 1161124-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N(1H)-7-(1'-naphthoylamino)-4-methylquinolin-2(1H)-one
• 英文别名: N-(4-methyl-2-oxo-1H-quinolin-7-yl)naphthalene-1-carboxamide
• CAS: 1161124-46-4
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: CYSBUUYYKZKSOR-UHFFFAOYSA-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：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  喹诺酮 124 、 1-萘甲酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 以70%的产率得到N(1H)-7-(1'-naphthoylamino)-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Design and synthesis of 2-quinolones as antioxidants and antimicrobials: a rational approach

  摘要：

  As an important class of compounds, 2-quinolones are isomeric to 4-quinolones and isosteric to coumarins. The compounds that have 2-quinolone moiety are associated with interesting biologic activities such as antibacterial, anticancer, antiviral, cardiotonic, and N-methyl-D-aspartate receptor inhibitor functions, among others. In the current study, based on the rational approach, lead molecules of the 2-quinolone skeleton were designed for binding to the bacterial DNA gyrase subunit A. Docking simulations and quantitative structure activity relationship (QSAR) analysis were performed using the Molegro Virtual Docker and Sarchitech softwares. Based on these studies, the 7-amino-4-methylquinolin-2(1H)-one parent compound and its carboxamides (JST 1-15) were synthesized using Conrad Limpach synthesis. The synthesized test compounds then were characterized by thin-layer chromatography and melting point determination, as well as by ultraviolet, infrared (IR), (1)H-NMR, and MS studies. All synthesized and purified compounds were tested for antioxidant and antibacterial activity.

  DOI：

  10.1007/s00044-009-9184-x

文献信息

• Design and synthesis of 2-quinolones as antioxidants and antimicrobials: a rational approach
  作者：B. S. Jayashree、Seeja Thomas、Yogendra Nayak

  DOI：10.1007/s00044-009-9184-x

  日期：2010.3

  As an important class of compounds, 2-quinolones are isomeric to 4-quinolones and isosteric to coumarins. The compounds that have 2-quinolone moiety are associated with interesting biologic activities such as antibacterial, anticancer, antiviral, cardiotonic, and N-methyl-D-aspartate receptor inhibitor functions, among others. In the current study, based on the rational approach, lead molecules of the 2-quinolone skeleton were designed for binding to the bacterial DNA gyrase subunit A. Docking simulations and quantitative structure activity relationship (QSAR) analysis were performed using the Molegro Virtual Docker and Sarchitech softwares. Based on these studies, the 7-amino-4-methylquinolin-2(1H)-one parent compound and its carboxamides (JST 1-15) were synthesized using Conrad Limpach synthesis. The synthesized test compounds then were characterized by thin-layer chromatography and melting point determination, as well as by ultraviolet, infrared (IR), (1)H-NMR, and MS studies. All synthesized and purified compounds were tested for antioxidant and antibacterial activity.