6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(4-thiomorpholinyl)-3-quinolinecarboxylic acid | 88569-77-1

• 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: 6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(4-thiomorpholinyl)-3-quinolinecarboxylic acid
• 英文别名: 6-fluoro-1-(methylamino)-4-oxo-7-thiomorpholin-4-ylquinoline-3-carboxylic acid
• CAS: 88569-77-1
• 化学式: C₁₅H₁₆FN₃O₃S
• 分子量: 337.375
• InChiKey: HEASXVRPOKETGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 在 sodium hydroxide 、 乙酸酐 、 potassium carbonate 、 2,4-二硝基苯基羟胺 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(4-thiomorpholinyl)-3-quinolinecarboxylic acid
  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

文献信息

• 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.

  小说1-R-1,4-二氢-4-氧化-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，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。优选的化合物组包括Z.dbd.N为1-哌嗪基或4-低烷基-1-哌嗪基。
• New quinolone compounds and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0090424A1

  公开（公告）日：1983-10-05

  Novel 1-R-1,4-dihydro-4-oxo-6-fluoro-7-(Z=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=N is a heterocyclic group, useful as antibacterial agents, are prepared by reacting the corresponding 7-chloroquinoline derivatives with the appropriate heterocyclic compound, Z=NH. A preferred group of compounds are those where Z=N is 1-piperazinyl of 4-lower-alkyl-1-piperazinyl.

  新型 1-R-1,4-二氢-4-氧代-6-氟-7-(Z=N-)-喹啉羧酸及其酯类，其中 R 为氨基、低级烷基氨基、2-丙烯基氨基或二低级烷基氨基，R "为氢或低级烷基，Z=N 为杂环基团，可作为抗菌剂，通过相应的 7-氯喹啉衍生物与适当的杂环化合物 Z=NH 反应制备。 优选的一组化合物是 Z=N 为 1-哌嗪基或 4-低级烷基-1-哌嗪基的化合物。
• US4499091A
  申请人：——

  公开号：US4499091A

  公开（公告）日：1985-02-12
• Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: synthesis and structure-activity relationships
  作者：Mark P. Wentland、Denis M. Bailey、James B. Cornett、Richard A. Dobson、Ronald G. Powles、Roland B. Wagner

  DOI：10.1021/jm00375a003

  日期：1984.9

  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).