N-(3-chloro-4-fluorophenyl)-2-(6-methoxy-2-oxo-2H-chromen-7-yloxy)acetamide | 1387000-08-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(3-chloro-4-fluorophenyl)-2-(6-methoxy-2-oxo-2H-chromen-7-yloxy)acetamide
• 英文别名: N-(3-chloro-4-fluorophenyl)-2-(6-methoxy-2-oxochromen-7-yl)oxyacetamide
• CAS: 1387000-08-9
• 化学式: C₁₈H₁₃ClFNO₅
• 分子量: 377.756
• InChiKey: BPFBYTHTUGXLFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二氯-4-氟代-N-乙酰苯胺 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 N-(3-chloro-4-fluorophenyl)-2-(6-methoxy-2-oxo-2H-chromen-7-yloxy)acetamide
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel scopoletin derivatives

  摘要：

  Twenty scopoletin derivatives were developed by a systematic combinatorial chemical approach and their chemical structures were confirmed by MS, IR, H-1 NMR spectra and elemental analysis. Primary screening against mammary (MCF-7 and MDA-MB 231) and colon (HT-29) carcinoma cells indicated that five compounds (8d, 8g, 8j, 11b and 11g) displayed high antitumor potencies with IC50 values below 20 mu M whereas scopoletin showed IC50 values above 100 mu M. Moreover, the most promising compound 11g was more active than 5-fluorouracil. These results clearly indicated that the modification of the scopoletin structure could greatly increase its antitumor activity in vitro. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.014

文献信息

• Synthesis and in vitro antitumor activity of novel scopoletin derivatives
  作者：Wukun Liu、Jie Hua、Jinpei Zhou、Huibin Zhang、Haiyang Zhu、Yanhua Cheng、Ronald Gust

  DOI：10.1016/j.bmcl.2012.06.014

  日期：2012.8

  Twenty scopoletin derivatives were developed by a systematic combinatorial chemical approach and their chemical structures were confirmed by MS, IR, H-1 NMR spectra and elemental analysis. Primary screening against mammary (MCF-7 and MDA-MB 231) and colon (HT-29) carcinoma cells indicated that five compounds (8d, 8g, 8j, 11b and 11g) displayed high antitumor potencies with IC50 values below 20 mu M whereas scopoletin showed IC50 values above 100 mu M. Moreover, the most promising compound 11g was more active than 5-fluorouracil. These results clearly indicated that the modification of the scopoletin structure could greatly increase its antitumor activity in vitro. (c) 2012 Elsevier Ltd. All rights reserved.