6-氟-1,4-二氢-4-氧代-1-苯基-7-(1-哌嗪基)-3-喹啉羧酸 | 98106-13-9

• 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: 6-氟-1,4-二氢-4-氧代-1-苯基-7-(1-哌嗪基)-3-喹啉羧酸
• 中文别名: 6-氟-4-羰基-1-苯基-7-(哌嗪-1-基)-1,4-二氢喹啉-3-羧酸
• 英文名称: 1-phenyl-6-fluoro-7-piperazin-1-yl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-phenyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid；3-Quinolinecarboxylic acid, 6-fluoro-1,4-dihydro-4-oxo-1-phenyl-7-(1-piperazinyl)-；6-fluoro-4-oxo-1-phenyl-7-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 98106-13-9
• 化学式: C₂₀H₁₈FN₃O₃
• 分子量: 367.38
• InChiKey: LNDZQOCPDSKPRL-UHFFFAOYSA-N

物化性质

• 沸点：
  608.4±55.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-二氯-5-氟-Β-氧代苯丙酸乙酯 在 sodium hydroxide 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 6-氟-1,4-二氢-4-氧代-1-苯基-7-(1-哌嗪基)-3-喹啉羧酸
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

  摘要：

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

  DOI：

  10.1021/jm00149a003

文献信息

• Effect of Lipophilicity at N-1 on Activity of Fluoroquinolones against Mycobacteria
  作者：Thomas E. Renau、Joseph P. Sanchez、Martin A. Shapiro、Julie A. Dever、Stephen J. Gracheck、John M. Domagala

  DOI：10.1021/jm00015a021

  日期：1995.7

  The dramatic increase in drug resistant Mycobacterium tuberculosis has caused a resurgence in research targeted toward these organisms. As part of a systematic study to optimize the quinolone antibacterials against mycobacteria, we have prepared a series of N-1-phenylsubstituted derivatives to explore the effect of increasing lipophilicity on potency at this position. The compounds, synthesized by the modification of a literature procedure, were evaluated for activity against Gram-negative and Gram-positive bacteria, Mycobacterium fortuitum and Mycobacterium smegmatis, and the results correlated with log P, pK(a), and other attributes. The activity of the compounds against the rapidly growing, less hazardous organism M. fortuitum was used as a measure of M, tuberculosis activity. The results demonstrate that increasing lipophilic character by itself does not correlate with increased potency against mycobacteria. Rather, intrinsic activity against Gram-negative and/or Gram-positive bacteria is the governing factor for corresponding activity against mycobacteria.
• Quinoline antibacterial compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0131839B1

  公开（公告）日：1989-02-01
• CHU, DANIEL T.
  作者：CHU, DANIEL T.

  DOI：——

  日期：——
• US4730000A
  申请人：——

  公开号：US4730000A

  公开（公告）日：1988-03-08
• US4994599A
  申请人：——

  公开号：US4994599A

  公开（公告）日：1991-02-19