4-(3-Chlorofuro[2,3-b]quinolin-4-yl)oxybenzaldehyde

• 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: 4-(3-Chlorofuro[2,3-b]quinolin-4-yl)oxybenzaldehyde
• 化学式: C₁₈H₁₀ClNO₃
• 分子量: 323.735
• InChiKey: KWHWUJONJXGFRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-(3-Chlorofuro[2,3-b]quinolin-4-yl)oxybenzaldehyde 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以34%的产率得到(4-Furo[2,3-b]quinolin-4-yloxyphenyl)methanol
  参考文献：
  名称：

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

  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 4-anilinofuro[2,3-b]quinoline and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities by reaction of 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-NH2 or Ar-OH. Compounds 6a and 15 were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.5 and 16.4 muM, respectively. Compounds 2b, 6a, 10, and 15 also showed potent inhibitory activity (IC50 = 7.2-29.4 muM) for the secretion of lysosomal enzyme and beta-glucuronidase from neutrophils. These results also indicated that oxime derivatives are more potent than the respective ketone precursors (6a greater than or equal to 2a; 7a greater than or equal to 3), and the substituent such as Me at the oxime decreased inhibitory activity (6a greater than or equal to 6b; 7a greater than or equal to 7b). Among these derivatives, compound 6a showed the most potent activity with IC50 values of 6.5-11.6 muM for the inhibition of mast cell degranulation and neutrophil degranulation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.051
• 作为产物：
  描述：

  3,4-dichlorofuro[2,3-b]quinoline 、 对羟基苯甲醛 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以72%的产率得到4-(3-Chlorofuro[2,3-b]quinolin-4-yl)oxybenzaldehyde
  参考文献：
  名称：

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

  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 4-anilinofuro[2,3-b]quinoline and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities by reaction of 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-NH2 or Ar-OH. Compounds 6a and 15 were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.5 and 16.4 muM, respectively. Compounds 2b, 6a, 10, and 15 also showed potent inhibitory activity (IC50 = 7.2-29.4 muM) for the secretion of lysosomal enzyme and beta-glucuronidase from neutrophils. These results also indicated that oxime derivatives are more potent than the respective ketone precursors (6a greater than or equal to 2a; 7a greater than or equal to 3), and the substituent such as Me at the oxime decreased inhibitory activity (6a greater than or equal to 6b; 7a greater than or equal to 7b). Among these derivatives, compound 6a showed the most potent activity with IC50 values of 6.5-11.6 muM for the inhibition of mast cell degranulation and neutrophil degranulation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.051

文献信息

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

  DOI：10.1016/j.bmc.2003.10.051

  日期：2004.1

  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 4-anilinofuro[2,3-b]quinoline and 4-phenoxyfuro[2,3-b]quinoline derivatives and evaluated their anti-inflammatory activities by reaction of 3,4-dichlorofuro[2,3-b]quinoline with appropriate Ar-NH2 or Ar-OH. Compounds 6a and 15 were proved to be more potent than the reference inhibitor, mepacrine for the inhibition of rat peritoneal mast cell degranulation with IC50 values of 6.5 and 16.4 muM, respectively. Compounds 2b, 6a, 10, and 15 also showed potent inhibitory activity (IC50 = 7.2-29.4 muM) for the secretion of lysosomal enzyme and beta-glucuronidase from neutrophils. These results also indicated that oxime derivatives are more potent than the respective ketone precursors (6a greater than or equal to 2a; 7a greater than or equal to 3), and the substituent such as Me at the oxime decreased inhibitory activity (6a greater than or equal to 6b; 7a greater than or equal to 7b). Among these derivatives, compound 6a showed the most potent activity with IC50 values of 6.5-11.6 muM for the inhibition of mast cell degranulation and neutrophil degranulation. (C) 2003 Elsevier Ltd. All rights reserved.