4-hydroxy-quinoline-3,8-dicarboxylic acid | 402580-02-3

• 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: 4-hydroxy-quinoline-3,8-dicarboxylic acid
• 英文别名: 4-Hydroxy-chinolin-3,8-dicarbonsaeure；4-oxo-1H-quinoline-3,8-dicarboxylic acid
• CAS: 402580-02-3
• 化学式: C₁₁H₇NO₅
• mdl: MFCD16171427
• 分子量: 233.18
• InChiKey: YYLVBIBWUBXXRA-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-quinoline-3,8-dicarboxylic acid 在 重氮甲烷 、 喹啉 、 乙醚 、 copper oxide-chromium oxide 作用下， 生成 4-氧代-1,4-二氢-喹啉-8-羧酸甲酯
  参考文献：
  名称：

  Degradation Studies on Apo- and Dehydro-apo-β-erythroidine^1,2

  摘要：

  DOI：

  10.1021/ja01130a051
• 作为产物：
  描述：

  3-Ethoxycarbonyl-4-hydroxy-8-methoxycarbonyl-chinolin 在 sodium hydroxide 作用下， 生成 4-hydroxy-quinoline-3,8-dicarboxylic acid
  参考文献：
  名称：

  Degradation Studies on Apo- and Dehydro-apo-β-erythroidine^1,2

  摘要：

  DOI：

  10.1021/ja01130a051

文献信息

• Cyclization of Phenacyl 2-{[2,2-Di(ethoxycarbonyl)vinyl]amino}benzoate
  作者：Pavel Hradil、Lubomír Kvapil、Jan Hlaváč、Karel Lemr、Juraj Ševčík

  DOI：10.1135/cccc19980520

  日期：——

  Reaction of phenacyl anthranilate (1) with diethyl (ethoxymethylidene)malonate afforded phenacyl 2-[2,2-di(ethoxycarbonyl)vinyl]amino}benzoate (2) which on heating in polyphosphoric acid underwent degradation. Thermal cyclization of 2 in diphenyl ether gave phenacyl 3-(ethoxycarbonyl)-4-oxo-1,4-dihydroquinoline-8-carboxylate (4). The phenacyl group did not cyclize even on prolonged heating at 250 °C. Heating in sulfuric acid resulted in hydrolysis of the ethyl ester under formation of 4-oxo-8-[(phenacyloxy)carbonyl]-1,4-dihydroquinoline-3-carboxylic acid (6). The structure of 4 was confirmed by an independent synthesis.

  苯乙酰基蒽酸酯（1）与乙基（乙氧甲基）丙二酸二乙酯反应，形成苯乙酰基2-[2,2-二(乙氧羰基)乙烯基]氨基}苯甲酸酯（2），在聚磷酸中加热降解。在二苯醚中，2经热环化反应生成苯乙酰基3-(乙氧羰基)-4-氧代-1,4-二氢喹啉-8-羧酸酯（4）。即使在250℃的长时间加热下，苯乙酰基也不会环化。在硫酸中加热会导致乙酰基酯水解，生成4-氧代-8-[(苯乙酰氧)羰基]-1,4-二氢喹啉-3-羧酸（6）。4的结构已通过独立合成确认。
• Evaluation of 3-Carboxy-4(1<i>H</i>)-quinolones as Inhibitors of Human Protein Kinase CK2
  作者：Andriy G. Golub、Olexander Ya. Yakovenko、Volodymyr G. Bdzhola、Vladislav M. Sapelkin、Piotr Zien、Sergiy M. Yarmoluk

  DOI：10.1021/jm050048t

  日期：2006.11.1

  Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitorss3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC50 = 0.3 mu M) and 4-oxo-1,4-dihydrobenzo[h] quinoline-3-carboxylic acid (9) (IC50 = 1 AM), are ATP competitive (K-i values are 0.06 and 0.28 mu M, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.
• OZEKI KOHJI; ISHIZUKA YASUHIRO; SAWADA MASAHIRO; ICHIKAWA TERU; SATO MAKO+, J. PHARM. SOC. JAP., 107,(1987) N 2, 123-134
  作者：OZEKI KOHJI、 ISHIZUKA YASUHIRO、 SAWADA MASAHIRO、 ICHIKAWA TERU、 SATO MAKO+

  DOI：——

  日期：——
• AGENTS FOR USE IN THE TREATMENT OF CARDIOVASCULAR AND INFLAMMATORY DISEASES STRUCTURALLY BASED ON 4(1 H)-QUINOLONE
  申请人：UCL Business PLC

  公开号：US20170066722A1

  公开（公告）日：2017-03-09

  The present invention provides a compound of formula I, a tautomer thereof, or a pharmaceutically acceptable salt or N-oxide thereof for use in the treatment or prevention of cardiovascular disease or of an inflammatory disease or condition: wherein: V is N or CR 3 ; X is N or CR 4 ; Y is N or CR 5 ; Z is N or CR 6 ; B is —(C═O)R 1 , a 5- to 10-membered heteroaryl group, or a group -L′″-NRR′, wherein R and R′ are the same or different and each represents a hydrogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group; R 1 is a 5- to 10-membered heterocyclyl group, or —OR′, wherein R′ is a hydrogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group, or R 1 is a proteinogenic α amino acid, which is linked to the carbonyl moiety in the compound of formula (I) via the α amino group, which amino acid is optionally esterified at the α carboxylic acid group with a C 1 -C 6 alkyl group or a C 6 -C 10 aryl group, or R 1 is —NR″R′″, —NR IV -L′″-CONR″R′″, or —NR IV -L′″-COOR, wherein R, R″, R′″ and R IV are the same or different and each represents a hydrogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group; either (a) W is N and R 9 and R 2 together form a bond, or (b) W is CR 8 , R 8 and R 9 together form a bond and R 2 is a hydrogen atom, or a C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, 5- to 10-membered heteroaryl, 5- to 10-membered heterocyclyl, -L′-A 2 , C 3 -C 10 cycloalkyl, or —COOR′ group, wherein R′ is a hydrogen atom or C 1 -C 6 alkyl group, or, when Z is a moiety CR 6 , R 2 may form, together with R 6 and the carbon and nitrogen atoms which connect R 2 and R 6 in the formula (I), a 5- to 6-membered heterocyclic ring; R 3 is a hydrogen atom, a halogen atom, or a hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, nitro, or —NR′R″ group, wherein R′ and R″ are the same or different and each represent a hydrogen atom or C 1 -C 6 alkyl group; R 4 and R 5 are the same or different and each represent a hydrogen atom, a halogen atom, or a hydroxyl, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, nitro, —NR′R″, —CO 2 R′″, C 6 -C 10 aryl, 5- to 10-membered heteroaryl, 5 to 10-membered heterocyclyl, or —CO—(C 1 -C 6 alkyl) group, wherein R′, R″ and R′″ are the same or different and each represent a hydrogen atom or C 1 -C 6 alkyl group, or R 4 and R 5 and the carbon atoms bonded to R 4 and R 5 together form a 5- to 6-membered heterocyclic ring; R 6 is a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or —CO 2 R′ group, wherein R′ is hydrogen or C 1 -C 6 alkyl, or, when W is a moiety CR 8 , R 6 may form, together with R 2 and the carbon and nitrogen atoms which connect R 6 and R 2 in the formula (I), a 5- to 6-membered heterocyclic ring; R 7 is a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl group, A 2 represents a C 6 -C 10 aryl or 5- to 10-membered heteroaryl group; L′, and L′″ are the same or different and each represent a C 1 -C 6 alkylene, C 2 -C 6 alkenylene, or C 2 -C 6 alkynylene group; said aryl, heteroaryl, cycloalkyl and heterocyclyl groups being unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, —SOR, —SO 2 R, —NR′R″, —NR′(C═O)R″, —COOR, nitro and cyano substituents, wherein R, R′ and R″ are the same or different and each represents a hydrogen atom or C 1 -C 4 alkyl group.
• Degradation Studies on Apo- and Dehydro-apo-β-erythroidine^1,2
  作者：M. F. Grundon、V. Boekelheide

  DOI：10.1021/ja01130a051

  日期：1952.5