2-carboethoxy-5-chloro-1,3-oxazolo-[4,5-h]quinoline | 88362-76-9

• 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: 2-carboethoxy-5-chloro-1,3-oxazolo-[4,5-h]quinoline
• 英文别名: Ethyl 5-chloro[1,3]oxazolo[4,5-h]quinoline-2-carboxylate；ethyl 5-chloro-[1,3]oxazolo[4,5-h]quinoline-2-carboxylate
• CAS: 88362-76-9
• 化学式: C₁₃H₉ClN₂O₃
• 分子量: 276.679
• InChiKey: HEEGWATWPPIDTN-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  432.0±48.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-carboethoxy-5-chloro-1,3-oxazolo-[4,5-h]quinoline 生成 5-Chloro-[1,3]oxazolo[4,5-h]quinoline-2-carboxylic acid
  参考文献：
  名称：

  MUSSER, J. H.;BROWN, R. E.

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯-8-羟基喹啉 在 sodium dithionite 、 硫酸 、 硝酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 2-carboethoxy-5-chloro-1,3-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。
• Method of prevention and treatment of peptic ulcers
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04831040A1

  公开（公告）日：1989-05-16

  Disclosed is a method for prophylactic and therapeutic treatment of peptic ulcers which comprises the administration of a pharmaceutical composition containing a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereon, wherein 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, aminolakyl, or carboxyalkyl, Z is oxygen, sulfur or nitrogen, X is cyano, carbalkoxyl, carboxyl, formuloximino, tetrazolyl, carbalkoxyalky or caboxyalkyl, and m is 0 or 1, in admixture or in association with a pharmaceutically acceptable carrier.

  揭示了一种用于预防和治疗消化性溃疡的方法，包括给予含有化合物的药物组合物，该化合物的结构式为##STR1##或其药用可接受的盐，其中R.sub.1和R.sub.2独立地为氢、低碳烷基、卤素、三氟甲基、氨基、低碳烷基氨基、低酰胺基、氰基、芳基、芳基/低碳烷基、硝基、低炔基、低烯基、低碳烷基砜基、低碳烷基砜基、低碳氧基羰基、羧基、低碳氧基、低碳酰基或低烯酰基，Y为氧、硫、氮或R.sub.3 N，其中R.sub.3为氢、低碳烷基、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、羧酰氧烷氧基、羧基、甲酰氧基、四唑基、羧酰氧烷基或羧酰氧基，m为0或1，与药用可接受的载体混合或与之结合。
• Certain 1,3-oxazolo[4,5H]quinolines useful as anti-allergy agents
  申请人：USV Pharmaceutical Corporation

  公开号：US04522947A1

  公开（公告）日：1985-06-11

  New quinoline compound, and the corresponding 1,2-; 1,3-; and 1,4-benzodiazines, the quinoline compounds being of the formula: ##STR1## and salts thereof, wherein 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, carbalkoxyl, 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-苯并二氮杂环化合物，其中喹啉化合物的化学式为：##STR1##及其盐，其中R.sub.1和R.sub.2独立地是氢、较低烷基、卤素、三氟甲基、氨基、较低烷基氨基、较低酰胺基、氰基、芳基、芳基/较低烷基、硝基、较低炔基、较低烯基、较低烷基亚砜基、较低烷基磺酰基、较低烷氧羰基、羧基、较低烷氧基、较低脂酰基或较低烯酰基，Y为氧、硫、氮或R.sub.3 N，其中R.sub.3为氢、较低烷基、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、羰基烷氧基、羧基、甲氧基亚胺基、四唑基、羰基烷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/或用作制备用于治疗哮喘的化合物的中间体。
• New quinoline and related compounds useful as anti-allergy agents
  申请人：RORER INTERNATIONAL (OVERSEAS) INC.

  公开号：EP0090360A2

  公开（公告）日：1983-10-05

  New quinoline compound, and the corresponding 1,2-; 1,3-; and 1,4-benzodiazines, the quinoline compounds being of the formula: and salts thereof, wherein R1 and R2 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 R3N wherein R3 is hydrogen, lower alkyl, alkenyl, alkynyl, aryl, aralkyl, acyl, aminoalkyl, or carboxyalkyl, Z is oxygen, sulfur or nitrogen, X is cyano, carbalkoxyl, 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-苯并二氮杂卓，这些喹啉化合物的式为 及其盐类，其中 R1和R2独立地为氢、低级烷基、卤代、三氟甲基、氨基、低级烷基氨基、低级酰氨基、氰基、芳基、芳基/低级亚烷基、硝基、低级炔基、低级烯基、低级烷基亚磺酰基、低级烷基磺酰基、低级烷氧基羰基、低级羧酰基、低级烷氧基羰基、低级烷氧基羰基、低级烷氧基羰基、Y 是氧、硫、氮或 R3N，其中 R3 是氢、低级烷基、烯基、炔基、芳基、芳烷基、酰基、氨基烷基或羧基、 Z为氧、硫或氮，X为氰基、碳烷氧基、羧基、甲酰亚胺基、四唑基、碳烷氧基烷基或羧基，m为0或1，可用作药物，特别是治疗哮喘的药物，和/或用作制备治疗哮喘的化合物的中间体。
• Use of quinoline derivatives for making a medicament effective in the prevention and treatment of ulcers
  申请人：RORER INTERNATIONAL (OVERSEAS) INC.

  公开号：EP0327052A2

  公开（公告）日：1989-08-09

  Disclosed is the use of a compound of the formula or a pharmaceutically acceptable salt thereon, wherein R₁ and R₂ 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 R₃N wherein R₃ is hydrogen, lower alkyl, alkenyl, alkynyl, aryl, aralkyl, acyl, aminoalkyl, or carboxyalkyl, Z is oxygen, sulfur or nitrogen, Z is cyano, carbalkoxyl, carboxyl, formyloximino, tetrazolyl, carbalkoxyalkyl or carboxyalkyl, and m is 0 or 1, in admixture or in association with a pharmaceutically acceptable carrier for making a medicament effective in the prophylactic and therapeutic treatment of peptic ulcers.

  本发明公开了一种式化合物 或其药学上可接受的盐的用途，其中 R₁ 和 R₂ 独立地为氢、低级烷基、卤代、三氟甲基、氨基、低级烷基氨基、低级酰氨基、氰基、芳基、芳基/低级亚烷基、硝基、低级炔基、低级烯基、低级烷基亚磺酰基、低级烷基磺酰基、低级烷氧基羰基、羧基、低级烷氧基、低级烷酰基或低级烯酰基、 Y 是氧、硫、氮或 R₃N，其中 R₃ 是氢、低级烷基、烯基、炔基、芳基、芳烷基、酰基、氨基烷基或羧基烷基、 Z 是氧、硫或氮、 Z 是氰基、羰氧烷基、羧基、甲酰亚胺基、四唑基、羰氧烷基或羧基，以及 m 为 0 或 1、 与药学上可接受的载体混合或结合，制成对预防和治疗消化性溃疡有效的药物。