3,4-dimethoxy-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzamide | 1161124-44-2

• 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: 3,4-dimethoxy-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzamide
• 英文别名: 3,4-dimethoxy-N-(4-methyl-2-oxo-1H-quinolin-7-yl)benzamide
• CAS: 1161124-44-2
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: JWTDCZBCLNOFTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  喹诺酮 124 、 3,4-二甲氧基苯甲酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 以74%的产率得到3,4-dimethoxy-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzamide
  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.
• Elucidation of Structure-activity Relationship of 2-Quinolone Derivatives and Exploration of Their Antitumor Potential Through Bax-induced Apoptotic Pathway
  作者：Nitesh Kumar、Vasanth P. Raj、B. S. Jayshree、Sidhartha S. Kar、Arvind Anandam、Seeja Thomas、Prateek Jain、Amita Rai、C. M. Rao

  DOI：10.1111/j.1747-0285.2012.01402.x

  日期：2012.8

  3‐Aryl‐2‐quinolone derivates were extensively investigated for their inhibition of farnesyl transferase. Taking this as a cue, we studied the other possible mechanism of antitumor activity of 2‐quinolone derivates. A series of new 2‐quinolone derivatives have been synthesized and screened for their cytotoxicity by trypan blue assay on Ehrlich ascites carcinoma cells and MTT assay on MCF‐7 cells. Compound 1a (nJST) was found to be more effective in both studies with the lowest CTC50 value among all nine synthesized compounds. This compound was further screened on four different cell lines, viz. human breast adenocarcinoma (MCF‐7, MDA‐MB‐231), colon cancer (HCT‐15), murine melanoma (B16F10) cell lines for 24 and 48 h. The CTC50 value of the compound was found to be <10 μm. Compound 1a induced DNA damage which was revealed by DNA fragmentation studies and further confirmed by nuclear staining. The compound also showed significant elevation in Bax and reduction Bcl‐2 gene expression levels. Acute toxicity study in mice indicated that the compound is safe till 2000 mg/kg. Two different doses 50 and 100 mg/kg were selected and studied in Ehrlich ascites carcinoma model of cancer and have shown significant improvement in survival time and hematological parameters.