3-carbethoxy-5-chloro-2-oxo-3H-oxazolo<4,5-h>quinoline | 97000-08-3

• 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: 3-carbethoxy-5-chloro-2-oxo-3H-oxazolo<4,5-h>quinoline
• 英文别名: Ethyl 5-chloro-2-oxo-[1,3]oxazolo[4,5-h]quinoline-3-carboxylate
• CAS: 97000-08-3
• 化学式: C₁₃H₉ClN₂O₄
• 分子量: 292.678
• InChiKey: PNXFHJJKFLAPRS-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氯-8-羟基喹啉 在 sodium dithionite 、 硫酸 、 硝酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 3-carbethoxy-5-chloro-2-oxo-3H-oxazolo<4,5-h>quinoline
  参考文献：
  名称：

  Synthesis and antiallergic activities of 1,3-oxazolo[4,5-h]quinolines

  摘要：

  A series of new 1,3-oxazolo[4,5-h]quinolines has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE-mediated passive cutaneous anaphylaxis in the rat (PCA). After several modifications of the original lead, the most potent compound of the series was determined to be 5-chloro-1,3-oxazolo[4,5-h]quinoline-2-carboxylic acid methyl ester (4a). It has an IC50 of 0.3 microM in the RMC assay and an ED50 (intraperitoneal) of 0.1 mg/kg in the PCA test, which is 10 times and 60 times more potent than disodium cromoglycate (DSCG), respectively. Of greater importance, it is orally active (ED50 = 0.5 mg/kg) as an inhibitor of the PCA test.

  DOI：

  10.1021/jm00147a023

文献信息

• Synthesis and antiallergic activities of 1,3-oxazolo[4,5-h]quinolines
  作者：John H. Musser、Howard Jones、Stanley Sciortino、Kevin Bailey、Stephen M. Coutts、Atul Khandwala、Paula Sonnino-Goldman、Mitchell Leibowitz、Peter Wolf、Edward S. Neiss

  DOI：10.1021/jm00147a023

  日期：1985.9

  A series of new 1,3-oxazolo[4,5-h]quinolines has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE-mediated passive cutaneous anaphylaxis in the rat (PCA). After several modifications of the original lead, the most potent compound of the series was determined to be 5-chloro-1,3-oxazolo[4,5-h]quinoline-2-carboxylic acid methyl ester (4a). It has an IC50 of 0.3 microM in the RMC assay and an ED50 (intraperitoneal) of 0.1 mg/kg in the PCA test, which is 10 times and 60 times more potent than disodium cromoglycate (DSCG), respectively. Of greater importance, it is orally active (ED50 = 0.5 mg/kg) as an inhibitor of the PCA test.