7-N-cinnamoylamino-4-methylquinolin-2(1H)-one | 1161124-49-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 7-N-cinnamoylamino-4-methylquinolin-2(1H)-one
• 英文别名: N-(4-methyl-2-oxo-1H-quinolin-7-yl)-3-phenylprop-2-enamide
• CAS: 1161124-49-7
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: WTODXQPPZQLRQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  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-cinnamoylamino-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

• 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.
• 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.