2-氟-N-(3,5-二甲氧基苯基)苯甲酰胺 | 305834-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氟-N-(3,5-二甲氧基苯基)苯甲酰胺
• 英文名称: N-(3,5-Dimethoxy-phenyl)-2-fluoro-benzamide
• 英文别名: N-(3,5-dimethoxyphenyl)-2-fluorobenzamide
• CAS: 305834-41-7
• 化学式: C₁₅H₁₄FNO₃
• 分子量: 275.279
• InChiKey: GFKUKKSYVVVCIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氟-N-(3,5-二甲氧基苯基)苯甲酰胺 在 potassium tert-butylate 、 四氯化锡 作用下， 以 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 21.5h， 生成 2-(2-Fluoro-phenyl)-5,7-dimethoxy-1H-quinolin-4-one
  参考文献：
  名称：

  Antimitotic Activity of 5-Hydroxy-7-methoxy-2-phenyl-4-quinolones

  摘要：

  We report the synthesis of 5-hydroxy-7-methoxy-2-phenyl-4-quinolones and their biological activity as antitumor agents. These molecules were initially evaluated for their ability to induce cell cycle arrest in the G2/M phase. Compounds that showed significant G2/M cell cycle arrest were tested for antiproliferative activity using both the MTT assay and the NCI in vitro 60 cell line human tumor screen. The 5-hydroxy-7-methoxy-2-phenyl-4-quinolone (3a) and 2-(3-fluorophenyl)-5-hydroxy-7-methoxy-4-quinolone (3f) were the most active in the cell cycle arrest test whereas 3f was found to be the most active in the MTT assay. In terms of structural requirements, we found that the presence of a 5-hydroxyl group, a 7-methoxy group, and an unsubstituted N1 were essential for the antimitotic activity. In accordance with the literature, a fluoro group at the 3'- or 2'-position and a methoxy or a chloro group at the 3'-position were found to be highly advantageous for both the cell cycle arrest and the antiproliferative activities.

  DOI：

  10.1021/jm049876x
• 作为产物：
  描述：

  邻氟苯甲酰氯 、 3,5-二甲氧基苯胺 在 三乙胺 作用下， 生成 2-氟-N-(3,5-二甲氧基苯基)苯甲酰胺
  参考文献：
  名称：

  A convenient method for the synthesis of 3,5,7-trimethoxy-2-phenyl-4-quinolones

  摘要：

  The synthesis of 2-aryl-3,5,7-trimethoxy-4-quinoiones was accomplished in three steps starting from 3,5-dimethoxyaniline and an aroyl chloride. These structures might be used as potential flavonol analogs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01226-0

文献信息

• Antimitotic Activity of 5-Hydroxy-7-methoxy-2-phenyl-4-quinolones
  作者：Mohamed Hadjeri、Eva-Laure Peiller、Chantal Beney、Nabajyoti Deka、Martin A. Lawson、Charles Dumontet、Ahcène Boumendjel

  DOI：10.1021/jm049876x

  日期：2004.9.1

  We report the synthesis of 5-hydroxy-7-methoxy-2-phenyl-4-quinolones and their biological activity as antitumor agents. These molecules were initially evaluated for their ability to induce cell cycle arrest in the G2/M phase. Compounds that showed significant G2/M cell cycle arrest were tested for antiproliferative activity using both the MTT assay and the NCI in vitro 60 cell line human tumor screen. The 5-hydroxy-7-methoxy-2-phenyl-4-quinolone (3a) and 2-(3-fluorophenyl)-5-hydroxy-7-methoxy-4-quinolone (3f) were the most active in the cell cycle arrest test whereas 3f was found to be the most active in the MTT assay. In terms of structural requirements, we found that the presence of a 5-hydroxyl group, a 7-methoxy group, and an unsubstituted N1 were essential for the antimitotic activity. In accordance with the literature, a fluoro group at the 3'- or 2'-position and a methoxy or a chloro group at the 3'-position were found to be highly advantageous for both the cell cycle arrest and the antiproliferative activities.
• A convenient method for the synthesis of 3,5,7-trimethoxy-2-phenyl-4-quinolones
  作者：Chantal Beney、Mohamed Hadjeri、Anne-Marie Mariotte、Ahcène Boumendjel

  DOI：10.1016/s0040-4039(00)01226-0

  日期：2000.9

  The synthesis of 2-aryl-3,5,7-trimethoxy-4-quinoiones was accomplished in three steps starting from 3,5-dimethoxyaniline and an aroyl chloride. These structures might be used as potential flavonol analogs. (C) 2000 Elsevier Science Ltd. All rights reserved.