7-amino-5-chloro-8-hydroxyquinoline | 18471-93-7

• 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: 7-amino-5-chloro-8-hydroxyquinoline
• 英文别名: 5-Chlor-7-amino-8-hydroxy-chinolin；7-Amino-5-chloroquinolin-8-ol
• CAS: 18471-93-7
• 化学式: C₉H₇ClN₂O
• mdl: MFCD00043885
• 分子量: 194.62
• InChiKey: MAHRZBYJYLDQAY-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C(Solv: ethanol (64-17-5))
• 沸点：
  400.3±45.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-amino-5-chloro-8-hydroxyquinoline 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 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
• 作为产物：
  描述：

  5-氯-8-羟基喹啉 在 盐酸 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 硝酸 作用下， 以 水 为溶剂， 70.0 ℃ 、586.07 kPa 条件下， 反应 20.0h， 生成 7-amino-5-chloro-8-hydroxyquinoline
  参考文献：
  名称：

  取代的oxine抑制内皮细胞增殖和血管生成†

  摘要：

  两个取代的oxines， 硝基氧( 5 ) 和5-氯喹啉-8-基苯基氨基甲酸酯( 22 )，在旨在寻找新的抗血管生成剂的高通量筛选中被鉴定为命中。在先前的研究中，我们阐明了抗增殖活性的分子机制硝基氧 在内皮细胞中，包括对 2 型人的双重抑制 蛋氨酸氨肽酶 (MetAP2) 和 Sirtuin 1 (SIRT1)。构效关系研究 (SAR)硝基氧提供了许多惊喜，其中微小的修改产生了对人脐静脉内皮细胞 (HUVEC) 效力增加的 oxine 衍生物，但具有完全不同的未知机制。例如，5-nitrosoquinolin-8-ol( 33 ) 以亚微摩尔 IC 50抑制 HUVEC 生长，但不影响 MetAP2 或 MetAP1，仅对 SIRT1 显示出微弱的抑制作用。其他亚微摩尔抑制剂是5-aminoquinolin-8-ol( 34 ) 和8-磺胺喹啉( 32 )。氨基磺酸盐衍生物硝基氧( 48 )

  DOI：

  10.1039/c2ob06978d

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。
• Hydroxyquinoline Derivatives
  申请人：Schadt Oliver

  公开号：US20080312278A1

  公开（公告）日：2008-12-18

  Compounds of the formula I in which X, Y, R 1 , R 1′ , R 2 , R 3 have the meanings indicated in claim 1 , are inhibitors of cell proliferation and can be employed for the treatment of tumours.

  公式I中X、Y、R1、R1'、R2、R3的化合物具有所述含义，可抑制细胞增殖，可用于肿瘤治疗。
• Imidazo quinoline compounds useful as anti-allergy agents
  申请人：USV Pharmaceutical Corp.

  公开号：US04656281A1

  公开（公告）日：1987-04-07

  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 nitrogen or R.sub.3 N wherein R.sub.3 is hydrogen, lower alkyl, alkenyl, alkynyl, aryl aralkyl, acyl, aminoalkyl, or carboxyalkyl, Z is 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 intermediates in the preparation of compounds useful for treating asthma.

  喹啉化合物的公式为：##STR1##及其盐，其中R.sub.1和R.sub.2独立地为氢、低烷基、卤素、三氟甲基、氨基、低烷基氨基、低酰胺基、氰基、芳基、芳基/低烷基、硝基、低炔基、低烯基、低烷基亚磺酰基、低烷基磺酰基、低烷氧羰基、羧基、低烷氧基、低烷酰基或低烯酰基，Y为氮或R.sub.3 N，其中R.sub.3为氢、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为氮，X为氰基、碳酰氧基、羧基、甲酰羟肟基、四唑基、碳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/或用于制备用于治疗哮喘的化合物的中间体。
• Thiazolo[5,4-h]quinoline compounds useful as anti-allergy agents
  申请人：USV Pharmaceutical Corporation

  公开号：US04698346A1

  公开（公告）日：1987-10-06

  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，其中喹啉化合物的式子为：##STR1##以及其盐，其中R.sub.1和R.sub.2独立地为氢，低级烷基，卤素，三氟甲基，氨基，低级烷基氨基，低酰基氨基，氰基，芳基，芳基/低级烷基，硝基，低级炔基，低级烯基，低级烷基亚砜基，低级烷基磺酰基，低级烷氧羰基，羧基，低级烷氧基，低级烷酰基，或低级烯酰基，Y为氧，硫，氮或R.sub.3 N，其中R.sub.3为氢，低级烷基，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，羧基烷氧基，羧基，甲酰氧肟基，四唑基，羧基烷氧基烷基或羧基烷基，m为0或1，可用作药物，特别是用于哮喘的治疗，和/或作为用于治疗哮喘的化合物的中间体。
• 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.

  新的喹啉化合物及其相应的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##以及其盐，其中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/低碳基亚烷基、硝基、低炔基、低烯基、低烷基亚砜基、低烷基磺酰基、低烷氧羰基、羧基、低烷氧基、低烷酰基或低烯酰基，Y为氧、硫、氮或R.sub.3N，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、羧基烷氧基、羧基、甲酰肟基、四唑基、羧基烷氧基烷基或羧基烷基，m为0或1，可用作药物，特别是用于哮喘的治疗，和/或作为制备用于治疗哮喘的化合物的中间体。