N-(diaminomethylene)-4-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)diazenyl]benzenesulfonamide | 54987-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(diaminomethylene)-4-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)diazenyl]benzenesulfonamide
• 英文别名: N-carbamimidoyl-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylazo)-benzenesulfonamide；2-[4-[(3,5-dimethyl-1-phenylpyrazol-4-yl)diazenyl]phenyl]sulfonylguanidine
• CAS: 54987-51-8
• 化学式: C₁₈H₁₉N₇O₂S
• 分子量: 397.461
• InChiKey: ZBVHMAKDNUKQQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  磺胺脒 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 N-(diaminomethylene)-4-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)diazenyl]benzenesulfonamide
  参考文献：
  名称：

  Pyrazole and Nicotinonitrile Derivatives Synthesized from Sulfa Drugs, and Their Antibacterial Activity

  摘要：

  Utility of sulfadiazine and sulfaguanidine in synthesis of new series of pyrazoles and 2-pyridones is described. Diazotization of sulfadiazine that results in formation of diazonium salt 2 followed by coupling of the latter with active methylene compounds leads to hydrazinyl derivatives 3a-3d. Heterocyclization of compounds 3a-3c with hydrazine derivatives gives to a series of pyrazole derivatives 4-6. Similarly, a series of pyrazole derivatives 12-14 is developed from sulfaguanidine. Condensation of hydrazinyl derivatives 3a-3c with cyanoacetamide in the presence of a catalytic amount of piperidine gives 2-oxonicotinonitriles 15a-15c. Tests of the new synthesized compounds against four pathogenic gram (+ve) and gram (-ve) bacteria demonstrate their activity higher than that of the standard Amoxicillin.

  DOI：

  10.1134/s1070363219020270