1-(4-Furo[2,3-b]quinolin-4-yloxyphenyl)ethanone | 641144-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Furo[2,3-b]quinolin-4-yloxyphenyl)ethanone
• CAS: 641144-45-8
• 化学式: C₁₉H₁₃NO₃
• 分子量: 303.317
• InChiKey: FCKWPLBUVFUNEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-Furo[2,3-b]quinolin-4-yloxyphenyl)ethanone 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以91%的产率得到
  参考文献：
  名称：

  Synthesis and anti-inflammatory evaluation of 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives. Part 2

  摘要：

  Mast cells, neutrophils and macrophages are important inflammatory cells that have been implicated in the pathogenesis of acute and chronic inflammatory diseases. To explore a novel anti-inflammatory agent, we have synthesized certain 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities. The title compounds were synthesized by reaction of either 9-chloroacridine or 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-OH and their anti-inflammatory activities were studied on inhibitory effects on the activation of mast cells, neutrophils and macrophages. Four 9-(4formylphenoxy)acridine derivatives 2b-2e were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.1, 5.9, 13.5, and 4.7 muM, respectively. Compounds 2c, 3b, 3c, and 5a also showed potent inhibitory activity (IC50 = 4.3-18.3 muM) for the secretion of lysosomal enzyme and P-glucuronidase from neutrophils. In addition, 2d, 3a, and 4 inhibited TNF-alpha formation from the N9 cells (the brain resident macrophages) with IC50 vales less then 10 muM. These results indicated that acridine derivatives exhibited more potent anti-inflammatory activities than their respective furo[2,3-b]quinoline counterparts (4 vs 9; 5a vs 10a; 5b vs 10b). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00439-5
• 作为产物：
  描述：

  3,4-dichlorofuro[2,3-b]quinoline 在 Lindlar's catalyst 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 1-(4-Furo[2,3-b]quinolin-4-yloxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and anti-inflammatory evaluation of 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives. Part 2

  摘要：

  Mast cells, neutrophils and macrophages are important inflammatory cells that have been implicated in the pathogenesis of acute and chronic inflammatory diseases. To explore a novel anti-inflammatory agent, we have synthesized certain 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities. The title compounds were synthesized by reaction of either 9-chloroacridine or 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-OH and their anti-inflammatory activities were studied on inhibitory effects on the activation of mast cells, neutrophils and macrophages. Four 9-(4formylphenoxy)acridine derivatives 2b-2e were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.1, 5.9, 13.5, and 4.7 muM, respectively. Compounds 2c, 3b, 3c, and 5a also showed potent inhibitory activity (IC50 = 4.3-18.3 muM) for the secretion of lysosomal enzyme and P-glucuronidase from neutrophils. In addition, 2d, 3a, and 4 inhibited TNF-alpha formation from the N9 cells (the brain resident macrophages) with IC50 vales less then 10 muM. These results indicated that acridine derivatives exhibited more potent anti-inflammatory activities than their respective furo[2,3-b]quinoline counterparts (4 vs 9; 5a vs 10a; 5b vs 10b). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00439-5

文献信息

• Synthesis and anti-inflammatory evaluation of 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives. Part 2
  作者：Yeh-Long Chen、I-Li Chen、Chih-Ming Lu、Cherng-Chyi Tzeng、Lo-Ti Tsao、Jih-Pyang Wang

  DOI：10.1016/s0968-0896(03)00439-5

  日期：2003.9

  Mast cells, neutrophils and macrophages are important inflammatory cells that have been implicated in the pathogenesis of acute and chronic inflammatory diseases. To explore a novel anti-inflammatory agent, we have synthesized certain 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities. The title compounds were synthesized by reaction of either 9-chloroacridine or 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-OH and their anti-inflammatory activities were studied on inhibitory effects on the activation of mast cells, neutrophils and macrophages. Four 9-(4formylphenoxy)acridine derivatives 2b-2e were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.1, 5.9, 13.5, and 4.7 muM, respectively. Compounds 2c, 3b, 3c, and 5a also showed potent inhibitory activity (IC50 = 4.3-18.3 muM) for the secretion of lysosomal enzyme and P-glucuronidase from neutrophils. In addition, 2d, 3a, and 4 inhibited TNF-alpha formation from the N9 cells (the brain resident macrophages) with IC50 vales less then 10 muM. These results indicated that acridine derivatives exhibited more potent anti-inflammatory activities than their respective furo[2,3-b]quinoline counterparts (4 vs 9; 5a vs 10a; 5b vs 10b). (C) 2003 Elsevier Ltd. All rights reserved.