乙基1-氨基-7-氯-6-氟-4-氧代-1,4-二氢-3-喹啉羧酸酯 | 88569-30-6

• 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: 乙基1-氨基-7-氯-6-氟-4-氧代-1,4-二氢-3-喹啉羧酸酯
• 中文别名: 2(S)-[2-羰基-4(R)-丙基吡咯烷-1-基]丁酰胺；乙基1-氨基-7-氯-6-氟-4-氧亚基-1,4-二氢喹啉-3-甲酸基酯；乙基 1-氨基-7-氯-6-氟-4-氧亚基-1,4-二氢喹啉-3-甲酸基酯
• 英文名称: ethyl 1-amino-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate
• 英文别名: Ethyl 1-amino-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate；ethyl 1-amino-7-chloro-6-fluoro-4-oxoquinoline-3-carboxylate
• CAS: 88569-30-6
• 化学式: C₁₂H₁₀ClFN₂O₃
• 分子量: 284.674
• InChiKey: QXKFZOWUCALDEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙基1-氨基-7-氯-6-氟-4-氧代-1,4-二氢-3-喹啉羧酸酯 在 sodium hydroxide 、 乙酸酐 、 potassium carbonate 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 氨氟沙星
  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：

  7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 在 potassium carbonate 、 2,4-二硝基苯基羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以78%的产率得到乙基1-氨基-7-氯-6-氟-4-氧代-1,4-二氢-3-喹啉羧酸酯
  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.

  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。
• Synthesis of N-(1-Aziridinyl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acids
  作者：Sándor Bátori、Géza Tímári、András Messmer、Benjámin Podányi、Lelle Vasvárii-Debreczy、István Hermecz

  DOI：10.3987/com-97-7770

  日期：——

  A series of N-(1-aziridinyl)quinoline-3-carboxylic acid derivatives (e.g. 11a-f, 20a-g, 21a-d) have been synthesized by insertion reaction of nitrenes (e.g. ethyl 7-chloro-6-fluoro-1-nitreno-1,4-dihydro-4-oxoquinoline-3-carboxylate (9)) into double bond of different olefins (e.g. styrene (10a), see Schemes 2 and 4). The nitrenes were formed in situ by oxidation of N-aminoquinolin-4(1H)-one derivatives (8, 18a,b) using Pb(OAc)(4) as oxidizing agent.
• J. Med. Chem. 1984, 27, 1103-1108
  作者：

  DOI：——

  日期：——
• New quinolone compounds and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0090424B1

  公开（公告）日：1986-05-28
• WENTLAND, M. P.;BAILEY, D, M.
  作者：WENTLAND, M. P.、BAILEY, D, M.

  DOI：——

  日期：——