7-Piperazinyl-6-fluoro-1-(1-methylethenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid | 115274-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-Piperazinyl-6-fluoro-1-(1-methylethenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
• 英文别名: 6-Fluoro-4-oxo-7-piperazin-1-yl-1-prop-1-en-2-yl-1,8-naphthyridine-3-carboxylic acid
• CAS: 115274-39-0
• 化学式: C₁₆H₁₇FN₄O₃
• 分子量: 332.334
• InChiKey: YEABGOYSRWPXJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-Piperazinyl-6-fluoro-1-(2-(phenylsulfinyl)-1-methylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 various solvent(s) 为溶剂， 反应 3.92h， 生成 7-Piperazinyl-6-fluoro-1-(1-methylethenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives

  摘要：

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

  DOI：

  10.1021/jm00123a005

文献信息

• Pyridonecarboxylic acids as antibacterial agents. XII. Synthesis and antibacterial activity of enoxacin analogues with a variant at position 1.
  作者：YOSHIRO NISHIMURA、AKIRA MINAMIDA、JUN-ICHI MATSUMOTO

  DOI：10.1248/cpb.36.1223

  日期：——

  Synthesis and antibacterial activity of enoxacin analogues [1-substituted 6-fluoro-1, 4-dihydro-4-oxo-7-(1-piperazinyl)-1, 8-naphthyridine-3-carboxylic acids] were studied. Alkyl, hydroxyalkyl, chloroalkyl, aralkyl and alkenyl groups were selected as substituents at position 1. Among the compounds prepared in this work, the 1-(2-chloroethyl) analogue is the most active.

  研究了恩诺沙星类似物[1-取代的 6-氟-1，4-二氢-4-氧代-7-(1-哌嗪基)-1，8-萘啶-3-羧酸]的合成和抗菌活性。在第 1 位上选择了烷基、羟烷基、氯烷基、芳基和烯基作为取代基。在制备的化合物中，1-（2-氯乙基）类似物的活性最高。
• WEBER, ABRAHAM;BOUZARD, DANIEL;ESSIZ, MUNIR;CESARE, PIERRE D.;JACQUET, JE+
  作者：WEBER, ABRAHAM、BOUZARD, DANIEL、ESSIZ, MUNIR、CESARE, PIERRE D.、JACQUET, JE+

  DOI：——

  日期：——
• NISHIMURA, YOSHIRO;MINAMIDA, AKIRA;MATSUMOTO, JUN-ICHI, CHEM. AND PHARM. BULL., 36,(1988) N 3, 1223-1228
  作者：NISHIMURA, YOSHIRO、MINAMIDA, AKIRA、MATSUMOTO, JUN-ICHI

  DOI：——

  日期：——
• Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives
  作者：D. Bouzard、P. Di Cesare、M. Essiz、J. P. Jacquet、P. Remuzon、A. Weber、T. Oki、M. Masuyoshi

  DOI：10.1021/jm00123a005

  日期：1989.3

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.