7-N-benzoylamino-4-methylquinolin-2(1H)-one | 1161124-23-7

• 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
• 英文名称: 7-N-benzoylamino-4-methylquinolin-2(1H)-one
• 英文别名: N(1H)-7-(benzoylamino)-4-methylquinolin-2(1H)-one；N-(4-methyl-2-oxo-1H-quinolin-7-yl)benzamide
• CAS: 1161124-23-7
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: KTYHKJLHUSXCSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  间苯二胺 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 生成 7-N-benzoylamino-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer activity evaluation of novel derivatives of 7-amino-4-methylquinolin-2(1H)-one

  摘要：

  In this study, we designed and synthesized sixteen new derivatives of 7-amino-4-methylquinolin-2(1H)-one with potential anticancer activity. The structures of synthesized compounds were confirmed by 1H and C-13 NMR. The activity of novel substances was evaluated by cell viability assay and wound healing assay. In vitro tests for series of sixteen novel compounds were performed. The results showed that examined compounds are selective for a cancer cells, but their activity for various types of cancer is different. Three of the new compounds presented the ability to inhibit cells migration. The novel compounds constitute a good starting point for further studies and optimization of structure for new therapeutically effective anti-cancerous drugs. Seven compounds. which showed the highest rate of cell inhibition, were selected for further studies.

  DOI：

  10.32383/appdr/79279

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.
• Synthesis and anticancer activity evaluation of novel derivatives of 7-amino-4-methylquinolin-2(1H)-one
  作者：Krzysztof Kubica、Przemyslaw Taciak、Agnieszka Czajkowska、Alicja Sztokfisz-Ignasiak、Rafal Wyrebiak、Izabela Mlynarczuk-Bialy、Jacek Malejczyk、Aleksander Mazurek

  DOI：10.32383/appdr/79279

  日期：2018.8.31

  In this study, we designed and synthesized sixteen new derivatives of 7-amino-4-methylquinolin-2(1H)-one with potential anticancer activity. The structures of synthesized compounds were confirmed by 1H and C-13 NMR. The activity of novel substances was evaluated by cell viability assay and wound healing assay. In vitro tests for series of sixteen novel compounds were performed. The results showed that examined compounds are selective for a cancer cells, but their activity for various types of cancer is different. Three of the new compounds presented the ability to inhibit cells migration. The novel compounds constitute a good starting point for further studies and optimization of structure for new therapeutically effective anti-cancerous drugs. Seven compounds. which showed the highest rate of cell inhibition, were selected for further studies.