6-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one | 1215036-46-6

• 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
• 英文名称: 6-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one
• 英文别名: 9-fluoro-2, 3-dihydro-6-[3-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)]-3-methyl-10-(4-methylpiperazin-1-yl)-[1,4]oxazino[2,3,4-ij]quinolin-7-one
• CAS: 1215036-46-6
• 化学式: C₁₉H₂₂FN₇O₂S
• 分子量: 431.494
• InChiKey: UEQPAQIQKILZCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  97.34
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 6-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one 、 丙酮 以 乙醇 为溶剂， 反应 6.0h， 以27%的产率得到9-fluoro-2,3-dihydro-6-[3-(4-amino-4,5-dihydro-1-(3-oxobutyl-5-sulfanylene-1H-1,2,4-triazol-3-yl))]-3-methyl-1,10-(4-methylpiperazin-1-y)-[1,4]oxazino[2,3,4-ij]quinolin-7-one
  参考文献：
  名称：

  Design, synthesis, and docking studies of novel ofloxacin analogues as antimicrobial agents

  摘要：

  A number of novel ofloxacin analogues were synthesized by modifying the carboxylic acid at C-6. To investigate the antimicrobial data on structural basis, in-silico docking studies of the tested compounds into the crystal structure of topoisomerase II using Autodock vina 4.0 program was performed in order to predict the affinity and orientation of the synthesized compounds at the activities. R (2) values show good agreement with predicted binding affinities obtained by molecular docking studies. Also, it is verified by in-vitro antimicrobial screening, where all the compounds were most active against Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis. Among these compounds 3a, 3b, 3f showed good MIC (0.125 mu g/ml).

  DOI：

  10.1007/s00044-011-9655-8
• 作为产物：
  描述：

  氧氟沙星 在 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 62.0h， 生成 6-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one
  参考文献：
  名称：

  Design, synthesis, and docking studies of novel ofloxacin analogues as antimicrobial agents

  摘要：

  A number of novel ofloxacin analogues were synthesized by modifying the carboxylic acid at C-6. To investigate the antimicrobial data on structural basis, in-silico docking studies of the tested compounds into the crystal structure of topoisomerase II using Autodock vina 4.0 program was performed in order to predict the affinity and orientation of the synthesized compounds at the activities. R (2) values show good agreement with predicted binding affinities obtained by molecular docking studies. Also, it is verified by in-vitro antimicrobial screening, where all the compounds were most active against Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis. Among these compounds 3a, 3b, 3f showed good MIC (0.125 mu g/ml).

  DOI：

  10.1007/s00044-011-9655-8

文献信息

• Synthesis and antitumor evaluation of fluoroquinolone C3 fused heterocycles (II): From triazolothiadiazines to pyrazolotriazoles
  作者：Guo Qiang Hu、Li Li Hou、Yong Yang、Lei Yi、Song Qiang Xie、Guo Qiang Wang、Nan Nan Duan、Tie Yao Chao、Xiao Yi Wen、Wen Long Huang

  DOI：10.1016/j.cclet.2011.01.018

  日期：2011.7

  To further expand an effective modified route for the shift from an antibacterial fluoroquinolone (FQ) to an antitumor FQ, two series of title compounds based on an isostere of the FQ C3 carboxylic group with two fused heterocyclic rings, [1,2,4]triazolo[3,4b][1,3,4]thiadiazine and pyrazolo[5,l-c][1,2,4]triazole, respectively, were designed and synthesized starting from the current antibacterial FQs, and their in vitro antitumor activity against L1210, CHO cell lines were evaluated via their respective IC(50) values. (C) 2011 Guo Qiang Hu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.