4-{5-[(2,4-Dinitrophenyl)sulfanyl]furan-3-yl}pyridine | 593247-77-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-{5-[(2,4-Dinitrophenyl)sulfanyl]furan-3-yl}pyridine
• 英文别名: 4-[5-(2,4-dinitrophenyl)sulfanylfuran-3-yl]pyridine
• CAS: 593247-77-9
• 化学式: C₁₅H₉N₃O₅S
• 分子量: 343.32
• InChiKey: ZIQZZVFHTHFBIH-UHFFFAOYSA-N

物化性质

• 沸点：
  532.1±50.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{5-[(2,4-Dinitrophenyl)sulfanyl]furan-3-yl}pyridine 在 吡啶 、 五氯化磷 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  TAK-599, a novel N-Phosphono type prodrug of anti-MRSA cephalosporin T-91825: synthesis, physicochemical and pharmacological properties

  摘要：

  Crystalline 1 (TAK-599) is a novel N-phosphono prodrug of anti-methicillin-resistant Staphylococcus aureus (MRSA) cephalosporin 2a (T-91825) that has high affinity for penicillin-binding protein (PBP) 2' (IC50; 0.90 mug/mL) and shows potent in vitro anti-MRSA activity (MIC against MRSA N133; 1.56 mug/mL), comparable to that of vancomycin (1.56 mug/mL). Although 2a had insufficient water solubility (2.3 mg/mL) for parenteral administration, 1 showed excellent water solubility (> 100 mg/mL, pH 7) as well as good chemical stability in the solid state and solution. In pharmacokinetic studies, when 1 was administered intravenously to rats and monkeys, it was rapidly converted into 2a in the blood. These results show that 1 (TAK-599) is a highly promising parenteral cephalosporin targeted for MRSA infection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00126-3
• 作为产物：
  描述：

  4-(furan-3-yl)pyridine 、 2,4-二硝基苯硫氯 在 三氯化铝 作用下， 以 硝基甲烷 为溶剂， 以90%的产率得到4-{5-[(2,4-Dinitrophenyl)sulfanyl]furan-3-yl}pyridine
  参考文献：
  名称：

  TAK-599, a novel N-Phosphono type prodrug of anti-MRSA cephalosporin T-91825: synthesis, physicochemical and pharmacological properties

  摘要：

  Crystalline 1 (TAK-599) is a novel N-phosphono prodrug of anti-methicillin-resistant Staphylococcus aureus (MRSA) cephalosporin 2a (T-91825) that has high affinity for penicillin-binding protein (PBP) 2' (IC50; 0.90 mug/mL) and shows potent in vitro anti-MRSA activity (MIC against MRSA N133; 1.56 mug/mL), comparable to that of vancomycin (1.56 mug/mL). Although 2a had insufficient water solubility (2.3 mg/mL) for parenteral administration, 1 showed excellent water solubility (> 100 mg/mL, pH 7) as well as good chemical stability in the solid state and solution. In pharmacokinetic studies, when 1 was administered intravenously to rats and monkeys, it was rapidly converted into 2a in the blood. These results show that 1 (TAK-599) is a highly promising parenteral cephalosporin targeted for MRSA infection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00126-3