8-chloro-1-cyclopropyl-6-fluoro-7-(3-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propylamino)pyrrolidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• 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: 8-chloro-1-cyclopropyl-6-fluoro-7-(3-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propylamino)pyrrolidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 8-Chloro-1-cyclopropyl-6-fluoro-7-[3-[[2-hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl]amino]pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid；8-chloro-1-cyclopropyl-6-fluoro-7-[3-[[2-hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl]amino]pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid
• 化学式: C₂₄H₂₆ClFN₆O₆
• 分子量: 548.958
• InChiKey: FHJPTGUAWPLSFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  克林沙星 在 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 49.0h， 生成 8-chloro-1-cyclopropyl-6-fluoro-7-(3-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propylamino)pyrrolidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, and Antimicrobial Evaluation of Novel Quinolone Imidazoles and Interactions with MRSA DNA

  摘要：

  A novel series of quinolone imidazoles as new type of antimicrobial agents were synthesized. Most compounds exhibited good bioactivities especially against MRSA even superior to reference drugs. They induced bacterial resistance more slowly than clinical drugs and gave low cytotoxicity to human cells. The pKa values of these compounds showed appropriate ranges to pharmacokinetic behaviors. The interactions between compound 8b, Cu2+ ion, and MRSA DNA revealed that compound 8b could intercalate into DNA through copper ion bridge to form a steady 8b–Cu2+–DNA ternary complex which might further block DNA replication to exert the powerful bioactivities. Study of compound 8b with human serum albumin indicated that compound 8b could be effectively stored and carried by human serum albumin.

  DOI：

  10.1111/cbdd.12532

文献信息

• Design and biological evaluation of novel quinolone-based metronidazole derivatives as potent Cu2+ mediated DNA-targeting antibacterial agents
  作者：Ling Zhang、Kannekanti Vijaya Kumar、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2015.06.041

  日期：2015.9

  A series of novel quinolone-based metronidazole derivatives as new type of antimicrobial agents were developed and characterized. Most of them gave good antibacterial activity towards the Gram-positive and negative bacteria. Noticeably, quinolone derivative 3i exhibited low MIC value of 0.25 mu g/mL against Pseudomonas aeruginosa, which was even superior to reference drugs Norfloxacin, Ciprofloxacin and Clinafloxacin. The further research revealed that compound 3i could intercalate into P. aeruginosa DNA through copper ion bridge to form a steady 3i-Cu2+-DNA ternary complex which might further block DNA replication to exert the powerful bioactivities. (C) 2015 Elsevier Ltd. All rights reserved.