3-acetyl-2-oxo-3H-oxazolo<4,5-h>quinoline | 97000-05-0

• 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-acetyl-2-oxo-3H-oxazolo<4,5-h>quinoline
• 英文别名: 3-Acetyl-2-oxo-3H-oxazolo[4,5-h]quinoline；3-acetyl-[1,3]oxazolo[4,5-h]quinolin-2-one
• CAS: 97000-05-0
• 化学式: C₁₂H₈N₂O₃
• 分子量: 228.207
• InChiKey: BDPCIZQRRMXTRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氯-8-羟基喹啉 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-acetyl-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

• 2-Oxo-1,3-oxazolo[4,5-h] quinolines useful as anti-allergy agents
  申请人：USV Pharmaceutical Corp.

  公开号：US04563463A1

  公开（公告）日：1986-01-07

  New quinoline compound, and the corresponding 1,2-; 1,3-; and 1,4-benzodiazines, the quinoline compounds being of the formulae: ##STR1## and salts thereof, wherein R is hydrogen, acyl, carboethoxy,(3-methoxyphen)acetyl,(2-phenyl)propionyl, dimethylcarbamoyl or methyl, R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, halo, trifluoromethyl, amino, lower alkyl amino, lower acylamino, cyano, aryl, aryl/lower alkylene, nitro, lower alkynyl, lower alkenyl, lower alkyl sulfinyl, lower alkyl sulfonyl, lower alkoxycarbonyl, carboxyl, lower alkoxy, lower alkanoyl, or lower alkenoyl, Y is oxygen, sulfur, nitrogen or R.sub.3 N wherein R.sub.3 is hydrogen, lower alkyl, alkenyl, alkynyl, aryl, aralkyl, acyl, aminoalkyl, or carboxyalkyl, Z is oxygen, sulfur or nitrogen, X is cyano, carbalkoxy, carboxyl, formyloximino, tetrazolyl, carbalkoxyalkyl or carboxyalkyl, and m is 0 or 1, are useful as medicinals, especially for treatment of asthma, and/or as intermediates in the preparation of compounds useful for treating asthma.

  新的喹啉化合物，以及相应的1,2-；1,3-；和1,4-苯二氮杂环化合物，其中喹啉化合物的化学式为：##STR1##及其盐，其中R为氢，酰基，羧乙氧基，(3-甲氧基苯)乙酰基，(2-苯基)丙酰基，二甲基氨基甲酰基或甲基，R.sub.1和R.sub.2分别为氢，低碳基，卤素，三氟甲基，氨基，低碳基氨基，低酰胺基，氰基，芳基，芳基/低碳基烯基，硝基，低炔基，低烯基，低碳基亚砜基，低碳基磺酰基，低碳氧羰基，羧基，低碳氧基，低碳酰基或低碳烯酰基，Y为氧，硫，氮或R.sub.3 N，其中R.sub.3为氢，低碳基，烯基，炔基，芳基，芳基烷基，酰基，氨基烷基或羧基烷基，Z为氧，硫或氮，X为氰基，羧酰氧基，羧基，甲氧基亚硝基，四唑基，羧酰氧基烷基或羧基烷基，m为0或1，可用作药物，特别是用于治疗哮喘，和/或作为制备用于治疗哮喘的化合物的中间体。
• MUSSER, J. H.;BROWN, R. E.
  作者：MUSSER, J. H.、BROWN, R. E.

  DOI：——

  日期：——
• US4563463A
  申请人：——

  公开号：US4563463A

  公开（公告）日：1986-01-07
• 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.