N-(diaminomethylene)-4-[(3,5-dimethyl-1H-pyrazol-4-yl)diazenyl]benzenesulfonamide | 54987-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(diaminomethylene)-4-[(3,5-dimethyl-1H-pyrazol-4-yl)diazenyl]benzenesulfonamide
• 英文别名: N-carbamimidoyl-4-(3,5-dimethyl-1H-pyrazole-4-ylazo)-benzenesulfonamide；N-(Diaminomethylene)-4-[(3,5-dimethyl-1H-pyrazol-4-yl)diazenyl]benzenesulfonamide；2-[4-[(3,5-dimethyl-1H-pyrazol-4-yl)diazenyl]phenyl]sulfonylguanidine
• CAS: 54987-50-7
• 化学式: C₁₂H₁₅N₇O₂S
• 分子量: 321.363
• InChiKey: GQNVBHNAXBUIBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  160
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(diaminomethylene)-4-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzenesulfonamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 以70%的产率得到N-(diaminomethylene)-4-[(3,5-dimethyl-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

文献信息

• Pyrazole and Nicotinonitrile Derivatives Synthesized from Sulfa Drugs, and Their Antibacterial Activity
  作者：H. A. El-Sayed、A. H. Moustafa、A. A. Fadda、K. E. Abd El-Rahman

  DOI：10.1134/s1070363219020270

  日期：2019.2

  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.