1-Methyl-6-nitro-4-oxo-1,4-dihydro-chinolin-3-carbonsaeure | 103648-39-1

• 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: 1-Methyl-6-nitro-4-oxo-1,4-dihydro-chinolin-3-carbonsaeure
• 英文别名: 1-Methyl-6-nitro-4-oxoquinoline-3-carboxylic acid
• CAS: 103648-39-1
• 化学式: C₁₁H₈N₂O₅
• 分子量: 248.195
• InChiKey: JFZQVKYCBYXHOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-Methyl-6-nitro-4-oxo-1,4-dihydro-chinolin-3-carbonsaeure 在 potassium permanganate 、 邻苯二甲酸二丁酯 、 水 、 硝酸 、 铜 、 sodium carbonate 作用下， 生成 1-methyl-3,6-dinitro-1H-quinoline-2,4-dione
  参考文献：
  名称：

  Price, Australian Journal of Scientific Research, Series A: Physical Sciences, 1949, vol. 2, p. 272,278

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Carboxy-N-methyl-cyclohexa-4-pyridon 在 硝酸 作用下， 生成 1-Methyl-6-nitro-4-oxo-1,4-dihydro-chinolin-3-carbonsaeure
  参考文献：
  名称：

  Price, Australian Journal of Scientific Research, Series A: Physical Sciences, 1949, vol. 2, p. 272,279

  摘要：

  DOI：

文献信息

• 7-(Pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0179239A2

  公开（公告）日：1986-04-30

  1-Ethyt-6-ftuoro-1,4-dihydro-7-(2,6-dimethy)-4-pyridinyt)-4-oxo-3-quinolinecarboxylic acid or salt thereof, a novel compound useful highly potent antibacterial agent with a broad spectrum of anti-microbial activity, is prepared by nitrating the corresponding 6-desfluoro compound to produce the corresponding 6-nitro compound, reducing the latter compound to produce the corresponding 6-amino compound and converting the 6-amino via its diazonium salt to said 6-fluoro compound. Said novel acid is also prepared via intermediates prepared by heating 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid to produce a mixture of 4-(2-fluorophenyl)-2,6-di-methylpyridine and 2,4-dimethyl-5H-[1]benzopyrano[3,4-c)pyridin-5-one, separating the components of said mixture and nitrating 4-(2-fluorophenyl)-2,6-dimethylpyridine to produce 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine.

  1-乙基-6-氟-1,4-二氢-7-(2,6-二甲基)-4-吡啶)-4-氧代-3-喹啉羧酸或其盐是一种新型化合物，是一种具有广谱抗微生物活性的高效抗菌剂、其制备方法是：硝化相应的 6-去氟化合物，生成相应的 6-硝基化合物；还原后者，生成相应的 6-氨基化合物；然后通过重氮盐将 6-氨基化合物转化为所述 6-氟化合物。所述新型酸也可以通过加热 4-(2-氟苯基)-2,6-二甲基-3,5-吡啶二羧酸生成 4-(2-氟苯基)-2,6-二甲基吡啶和 2、4-(2-氟苯基)-2,6-二甲基吡啶和 2,4-二甲基-5H-[1]苯并吡喃并[3,4-c]吡啶-5-酮的混合物，分离所述混合物的组分并硝化 4-(2-氟苯基)-2,6-二甲基吡啶，生成 4-(2-氟-5-硝基苯基)-2,6-二甲基吡啶。
• Drummond; Lahey, Australian Journal of Scientific Research, Series A: Physical Sciences, 1949, vol. <A> 2, p. 630,635
  作者：Drummond、Lahey

  DOI：——

  日期：——
• Drummond; Lahey, Australian Journal of Scientific Research, Series A: Physical Sciences, 1949, vol. 2, p. 630,635
  作者：Drummond、Lahey

  DOI：——

  日期：——
• Price, Australian Journal of Scientific Research, Series A: Physical Sciences, 1949, vol. <A> 2, p. 272,273, 279
  作者：Price

  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.