1-cyclopropyl-6-fluoro-7-[4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid | 1146978-12-2

• 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: 1-cyclopropyl-6-fluoro-7-[4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-8-methoxy-7-[3-methyl-4-[5-(1-methyl-5-nitroimidazol-2-yl)-1,3,4-thiadiazol-2-yl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1146978-12-2
• 化学式: C₂₅H₂₅FN₈O₆S
• 分子量: 584.588
• InChiKey: JGUXHDGKEMBZJS-UHFFFAOYSA-N

物化性质

• 熔点：
  272-274 °C(Solvent: Dimethylformamide; Water)
• 沸点：
  854.4±75.0 °C(predicted)
• 密度：
  1.72±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  191
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2-chloro-5-(1-methyl-4-nitro-1H-2-imidazolyl)-1,3,4-thiadiazole 、 加替沙星 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以62%的产率得到1-cyclopropyl-6-fluoro-7-[4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of nitroaryl thiadiazole–gatifloxacin hybrids

  摘要：

  A number of gatifloxacin analogues containing a nitroaryl-1,3,4-thiadiazole moiety attached to the piperazine ring at C-7 position were prepared and evaluated as antibacterial agents against a panel of Gram-positive and Gram-negative bacteria. Among synthesized compounds, nitrofuran analog 6a exhibited more potent inhibitory activity against Gram-positive bacteria including Staphylococcus epidermidis (MIC = 0.0078 mu g/mL), Bacillus subtilis (MIC = 0.0039 mu g/mL), Enterococcus faecalis (MIC = 0.125 mu g/mL) and Micrococcus luteus (MIC = 0.125 mu g/ml.), with respect to other synthesized compounds and reference drug gatifloxacin. The target compounds were also assessed for their cytotoxic activity against normal mouse fibroblast (NIH/3T3) cells using MTT assay. The results indicated that these compounds exhibit antibacterial activity at non-cytotoxic concentrations. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.09.012

文献信息

• Synthesis and antibacterial activity of nitroaryl thiadiazole–gatifloxacin hybrids
  作者：Seyyedehsamira Jazayeri、Mohammad Hassan Moshafi、Loghman Firoozpour、Saeed Emami、Saeed Rajabalian、Mitra Haddad、Farahnaz Pahlavanzadeh、Manzarbanoo Esnaashari、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2008.09.012

  日期：2009.3

  A number of gatifloxacin analogues containing a nitroaryl-1,3,4-thiadiazole moiety attached to the piperazine ring at C-7 position were prepared and evaluated as antibacterial agents against a panel of Gram-positive and Gram-negative bacteria. Among synthesized compounds, nitrofuran analog 6a exhibited more potent inhibitory activity against Gram-positive bacteria including Staphylococcus epidermidis (MIC = 0.0078 mu g/mL), Bacillus subtilis (MIC = 0.0039 mu g/mL), Enterococcus faecalis (MIC = 0.125 mu g/mL) and Micrococcus luteus (MIC = 0.125 mu g/ml.), with respect to other synthesized compounds and reference drug gatifloxacin. The target compounds were also assessed for their cytotoxic activity against normal mouse fibroblast (NIH/3T3) cells using MTT assay. The results indicated that these compounds exhibit antibacterial activity at non-cytotoxic concentrations. (C) 2008 Elsevier Masson SAS. All rights reserved.