4-[3,5-dicyano-6-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylthio)-4-(4-chlorophenyl)-2-oxopyridin-1(2H)-yl]-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide | 1621153-41-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[3,5-dicyano-6-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylthio)-4-(4-chlorophenyl)-2-oxopyridin-1(2H)-yl]-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-[[4-(4-chlorophenyl)-3,5-dicyano-1-[4-[(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl]-6-oxo-2-pyridyl]sulfanyl]tetrahydropyran-2-yl]methyl acetate；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(4-chlorophenyl)-3,5-dicyano-1-[4-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-6-oxopyridin-2-yl]sulfanyloxan-2-yl]methyl acetate
• CAS: 1621153-41-0
• 化学式: C₃₈H₃₄ClN₅O₁₃S₂
• 分子量: 868.299
• InChiKey: GNPGLDWEEXXSKL-KMQJBDDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  288
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  磺胺异噁唑 在 sodium ethanolate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 丙酮 为溶剂， 反应 28.0h， 生成 4-[3,5-dicyano-6-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylthio)-4-(4-chlorophenyl)-2-oxopyridin-1(2H)-yl]-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, antimicrobial evaluation and molecular docking studies of some new thiophene, pyrazole and pyridone derivatives bearing sulfisoxazole moiety

  摘要：

  Development of new antimicrobial agents is a good solution to overcome drug-resistance problems. In this context, new functionalized thiophene, acrylamide, arylhydrazone, pyrazole and pyridone derivatives bearing sulfisoxazole moiety were designed, synthesized and evaluated for their in vitro antibacterial and antifungal activities. Among the synthesized compounds, thiophene 4d and 6-thioglucosylpyridone 17 displayed significant antibacterial activities against Escherichia coli (MIC, 0.007 μg/mL vs gentamycin 1.95 μg/mL) and Bacillis subtilis (MIC, 0.007 μg/mL vs ampicillin 0.24 μg/mL), respectively. Whereas, the pyrazole 6 showed the highest antifungal activity against Aspergillus fumigates (MIC, 0.03 μg/mL vs amphotericin B 0.12 μg/mL). In general, most of the synthesized compounds exhibited better antimicrobial activities than sulfisoxazole; this might be attributed to the synergistic effect of the sulfonamide and attached heterocyclic moieties as well as the increased lipophilic characters of the synthesized compounds. Molecular docking studies indicated that the synthesized compounds could occupy both p-amino benzoic acid (PABA) and pterin binding pockets of the dihydropteroate synthase (DHPS), suggesting that the target compounds could act by the inhibition of microbial DHPS enzyme. The results provide important information for the future design of more potent antimicrobial agents.

  DOI：

  10.1016/j.ejmech.2014.07.052

文献信息

• Design, synthesis, antimicrobial evaluation and molecular docking studies of some new thiophene, pyrazole and pyridone derivatives bearing sulfisoxazole moiety
  作者：Tamer Nasr、Samir Bondock、Sameh Eid

  DOI：10.1016/j.ejmech.2014.07.052

  日期：2014.9

  Development of new antimicrobial agents is a good solution to overcome drug-resistance problems. In this context, new functionalized thiophene, acrylamide, arylhydrazone, pyrazole and pyridone derivatives bearing sulfisoxazole moiety were designed, synthesized and evaluated for their in vitro antibacterial and antifungal activities. Among the synthesized compounds, thiophene 4d and 6-thioglucosylpyridone 17 displayed significant antibacterial activities against Escherichia coli (MIC, 0.007 μg/mL vs gentamycin 1.95 μg/mL) and Bacillis subtilis (MIC, 0.007 μg/mL vs ampicillin 0.24 μg/mL), respectively. Whereas, the pyrazole 6 showed the highest antifungal activity against Aspergillus fumigates (MIC, 0.03 μg/mL vs amphotericin B 0.12 μg/mL). In general, most of the synthesized compounds exhibited better antimicrobial activities than sulfisoxazole; this might be attributed to the synergistic effect of the sulfonamide and attached heterocyclic moieties as well as the increased lipophilic characters of the synthesized compounds. Molecular docking studies indicated that the synthesized compounds could occupy both p-amino benzoic acid (PABA) and pterin binding pockets of the dihydropteroate synthase (DHPS), suggesting that the target compounds could act by the inhibition of microbial DHPS enzyme. The results provide important information for the future design of more potent antimicrobial agents.