4-喹啉甲酸 | 88569-39-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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
• 中文名称: 4-喹啉甲酸
• 中文别名: 7-氯-6-氟-1-(甲基氨基)-4-氧亚基-1,4-二氢喹啉-3-羧酸
• 英文名称: 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 7-chloro-6-fluoro-1-methylamino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid；7-chloro-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid；7-Chloro-6-fluoro-1,4-dihydro-1-methylamino-4-oxoquinoline-3-carboxylic acid；7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid；7-chloro-6-fluoro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid
• CAS: 88569-39-5
• 化学式: C₁₁H₈ClFN₂O₃
• 分子量: 270.648
• InChiKey: RCNJBEXSAWUACU-UHFFFAOYSA-N

物化性质

• 熔点：
  272-273 °C
• 沸点：
  443.0±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-喹啉甲酸 在 sodium hydroxide 、 palladium on activated charcoal 、 双氧水 作用下， 以 吡啶 为溶剂， 反应 36.0h， 生成 6-氟-1-[甲基(氧代)-lambda5-氮烷基]-7-(4-甲基-1-哌嗪基)-4-氧代-1,4-二氢-3-喹啉羧酸
  参考文献：
  名称：

  Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: synthesis and structure-activity relationships

  摘要：

  A series of novel 3-quinolinecarboxylic acid derivatives have been prepared and their antibacterial activity evaluated. These derivatives are characterized by fluorine attached to the 6-position and substituted amino groups appended to the 1- and 7-positions. Structure-activity relationship studies indicate that antibacterial potency is greatest when the 1-substituent is methylamino and the 7-substituent is either 4-methyl-1-piperazinyl, 16, or 1-piperazinyl, 21. Derivatives 16 and 21, the 1-methylamino analogues of pefloxacin and norfloxacin, respectively, show comparable in vitro and in vivo antibacterial potency to these two known agents. The activity (vs. Escherichia coli Vogel) of 16 (amifloxacin) is the following: in vitro MIC (microgram/mL) = 0.25; in vivo (mice) PD50 (mg/kg) = 1.0 (po), 0.6 (sc).

  DOI：

  10.1021/jm00375a003
• 作为产物：
  描述：

  2-(2,4-二氯-5-氟苯甲酰基)-3-乙氧基丙烯酸乙酯 在 氢氧化钾 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 4.67h， 生成 4-喹啉甲酸
  参考文献：
  名称：

  Grohe, Klaus; Heitzer, Helmut, Liebigs Annalen der Chemie, 1987, p. 871 - 880

  摘要：

  DOI：

文献信息

• Synthesis and Antibacterial Activity of Some Novel 1-Substituted 1,4-Dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic Acids. Potent Antistaphylococcal Agents
  作者：Michael Reuman、Sol J. Daum、Baldev Singh、Mark P. Wentland、Robert B. Perni、Patrick Pennock、Philip M. Carabateas、Monte D. Gruett、Manohar T. Saindane、Peter H. Dorff、Susan A. Coughlin、David M. Sedlock、James B. Rake、George Y. Lesher

  DOI：10.1021/jm00014a005

  日期：1995.7

  important for good Gram positive activity. For 1-cyclopropyl 7-(2,6-dimethyl-4-pyridinyl) derivatives, the 6-fluoro 4a, 8-fluoro 10d, 6,8-difluoro 10b, and 5,6,8-trifluoro 8, all provided equal antibacterial activity against Staphylococcus aureus ATCC 29213. There is also a correlation between the substitution on the 7-(4-pyridinyl) group and the Gram positive activity, particularly for S. aureus, clearly

  3-和4-（三烷基锡烷基）吡啶与7-溴或7-氯1取代的1,4-二氢-4-氧代-3-喹啉羧酸酯的钯催化偶联提供了相应的1取代的1， 4-二氢-4-氧代-7-吡啶基-3-喹啉羧酸。研究了这些衍生物的抗菌活性，发现革兰氏阳性活性的最佳1位和7位取代基分别是环丙基和4-（2,6-二甲基吡啶基）。我们发现对于所研究的氟取代的衍生物，氟在喹诺酮核上的位置或氟原子的数目对于良好的革兰氏阳性活性似乎并不重要。对于1-环丙基7-（2,6-二甲基-4-吡啶基）衍生物，6-氟4a，8-氟10d，6,8-二氟10b和5,6,8-三氟8 所有这些都对金黄色葡萄球菌ATCC 29213具有相同的抗菌活性。7-（4-吡啶基）基团的取代与革兰氏阳性活性之间也存在相关性，特别是对金黄色葡萄球菌，这清楚地表明2,6-二甲基吡啶基组是最佳的。在这项研究中，针对金黄色葡萄球菌ATCC 29213的最有效药物的MIC50值为0.0
• Substituted 4-pyridone 3-carboxylic acid derivatives, method for their
  申请人：Chemie Linz Gesellschaft m.b.H.

  公开号：US05045549A1

  公开（公告）日：1991-09-03

  New 4-Pyridone derivatives of General Formula are claimed ##STR1## in which R.sub.1 is methylamino,4-fluorophenyl, 2,4-difluorophenyl, R.sub.2 is hydrogen or a sulfur atom that is joined to the ring nitrogen by an ethylene bride, X is a hydrogen or a physiologically removable ester group and Y is a base of the general formula ##STR2## In formula IIa and IIb, R.sub.3 is hydrogen, lower alkyl, benzyl, formyl, acetonyl or a moiety of the formula ##STR3## Also claimed are the addition salts of compounds of formula I with pharmaceutically acceptable inorganic or organic acids or base and/or their hydrates. Also claimed are the methods of manufacture of compounds of formula I and their use as antibacterial agents.

  通用公式的新4-吡啶酮衍生物如下所述##STR1##其中R.sub.1为甲基氨基，4-氟苯基，2,4-二氟苯基，R.sub.2为氢或通过乙烯桥与环氮原子连接的硫原子，X为氢或生理可移除的酯基，Y为通用公式的碱##STR2##在公式IIa和IIb中，R.sub.3为氢，低碳烷基，苄基，甲酰基，丙酮基或公式##STR3##的基团。还声明了公式I化合物与药用可接受的无机或有机酸或碱的加合盐和/或其水合物。还声明了公式I化合物的制备方法及其用作抗菌剂的用途。
• A regiospecific synthesis of 1-methylamino-6-fluoro-7-(4-methylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  作者：Daniel T. W. Chu

  DOI：10.1002/jhet.5570220421

  日期：1985.7

  An efficient and regiospecific synthesis of 1-methylamino-6-fluoro-7-(4-methylpiperizin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (3) via an intramolecular nucleophilic displacement cyclization reaction is reported.

  通过分子内亲核取代环化反应有效和区域特异性合成1-甲基氨基-6-氟-7-（4-甲基哌嗪-1-基）-1,4-二氢-4-氧代喹啉-3-羧酸（3）被报道。
• Antibacterial agents III
  申请人：Warner-Lambert Company

  公开号：US04604401A1

  公开（公告）日：1986-08-05

  Novel 1-amino-naphthyridine- and quinoline-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.

  描述了作为抗菌剂的新型1-氨基萘啶和喹啉羧酸，以及它们的制备、配方和用于治疗细菌感染的方法。
• 1-Amino (or substituted
  申请人：Sterling Drug Inc.

  公开号：US04499091A1

  公开（公告）日：1985-02-12

  Novel 1-R-1,4-dihydro-4-oxo-6-fluoro-7-(Z.dbd.N--)-quinolinecarboxylic acids and esters thereof, where R is amino, lower-alkylamino, 2-propenylamino or di-lower-alkylamino, R" is hydrogen or lower-alkyl, and Z.dbd.N is a heterocyclic group, useful as antibacterial agents, are prepared by reacting the corresponding 7-chloroquinoline derivatives with the appropriate heterocyclic compound, Z.dbd.NH. A preferred group of compounds are those where Z.dbd.N is 1-piperazinyl or 4-lower-alkyl-1-piperazinyl.

  1-R-1,4-二氢-4-氧代-6-氟-7-(Z.dbd.N--)-喹啉羧酸及其酯类，其中R为氨基，低烷基氨基，2-丙烯基氨基或二-低烷基氨基，R"为氢或低烷基，Z.dbd.N为杂环基团，可用作抗菌剂，通过将相应的7-氯喹啉衍生物与适当的杂环化合物Z.dbd.NH反应制备而成。其中，首选化合物组是Z.dbd.N为1-哌嗪基或4-低烷基-1-哌嗪基。