ethyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)piperazin-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: ethyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Ethyl-6-fluoro-7-[4-[2-hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid；1-ethyl-6-fluoro-7-[4-[2-hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• 化学式: C₂₃H₂₇FN₆O₆
• 分子量: 502.502
• InChiKey: ZFTADACEXQUZCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  诺氟沙星 在 碳酸氢钠 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 56.0h， 生成 ethyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)piperazin-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

• 喹诺酮唑醇类化合物及其制备方法和应用
  申请人：西南大学

  公开号：CN104086534B

  公开（公告）日：2016-07-06

  本发明公开了一类通式(I)及其中间体(II)结构的具有抗微生物活性的喹诺酮唑醇类化合物，及其在药学领域可接受的盐的制备；本发明还涉及喹诺酮唑醇类化合物及其盐在作为抗感染药方面的应用。本发明所涉及的制备原料商业化程度高、便宜易得，制备路线短、方法简便。本发明的喹诺酮唑醇类化合物对革兰氏阳性菌、革兰氏阴性菌和真菌都有一定的抑制活性，可用于制备抗细菌和/或抗真菌药物。通用分子式中R1、R2、R3、R4、X和Im如权利要求书所定义。
• Design, Synthesis, and Antimicrobial Evaluation of Novel Quinolone Imidazoles and Interactions with MRSA DNA
  作者：Ling Zhang、Kannekanti Vijaya Kumar、Syed Rasheed、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1111/cbdd.12532

  日期：2015.10

  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.
• 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.