5-formyl-6-(p-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole-2-[N-(dimethylaminomethylidene)]sulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-formyl-6-(p-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole-2-[N-(dimethylaminomethylidene)]sulfonamide
• 英文别名: N'-[5-formyl-6-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]sulfonyl-N,N-dimethylmethanimidamide
• 化学式: C₁₅H₁₅N₅O₃S₂
• 分子量: 377.448
• InChiKey: DAYCITZPPIJIMJ-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  肼甲酰亚胺酰胺一氯化氢 、 5-formyl-6-(p-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole-2-[N-(dimethylaminomethylidene)]sulfonamide 以 乙醇 为溶剂， 反应 0.5h， 以70%的产率得到N'-[5-[(E)-(carbamimidoylhydrazono)methyl]-6-(p-tolyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]sulfonyl-N,N-dimethyl-formamidine
  参考文献：
  名称：

  Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives†

  摘要：

  6-Arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamides 3 on Vilsmeier-Haak reaction produced 5-formyl-6-arylimidazo[2, 1-b]1,3,3-thiadiazole-2-[N-(dimethylaminomethino)]sulfonamides 4, while 3 on treatment with potassium thiocyanate in the presence of bromine in acetic acid produced 5-thiocyanato-2-sulfonamides 6. Interaction of 4 with aminoguanidine hydrochloride in ethanol produced the corresponding 5-guanylhydrazone derivatives 5. Compounds 5 and 6 showed a high degree of antibacterial activity against both Escherichia coli and Staphylococcus aureus comparable to that of sulfamethoxazole and Norfloxacin. However, they were found to show moderate activity against Salmonella typhi, Pseudomonas aeruginosa and Pneumococci. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00166-5
• 作为产物：
  描述：

  2-溴-4'-甲基苯乙酮 以 乙醇 为溶剂， 生成 5-formyl-6-(p-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole-2-[N-(dimethylaminomethylidene)]sulfonamide
  参考文献：
  名称：

  Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives†

  摘要：

  6-Arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamides 3 on Vilsmeier-Haak reaction produced 5-formyl-6-arylimidazo[2, 1-b]1,3,3-thiadiazole-2-[N-(dimethylaminomethino)]sulfonamides 4, while 3 on treatment with potassium thiocyanate in the presence of bromine in acetic acid produced 5-thiocyanato-2-sulfonamides 6. Interaction of 4 with aminoguanidine hydrochloride in ethanol produced the corresponding 5-guanylhydrazone derivatives 5. Compounds 5 and 6 showed a high degree of antibacterial activity against both Escherichia coli and Staphylococcus aureus comparable to that of sulfamethoxazole and Norfloxacin. However, they were found to show moderate activity against Salmonella typhi, Pseudomonas aeruginosa and Pneumococci. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00166-5

文献信息

• Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives†
  作者：A Gadad

  DOI：10.1016/s0223-5234(00)00166-5

  日期：2000.9

  6-Arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamides 3 on Vilsmeier-Haak reaction produced 5-formyl-6-arylimidazo[2, 1-b]1,3,3-thiadiazole-2-[N-(dimethylaminomethino)]sulfonamides 4, while 3 on treatment with potassium thiocyanate in the presence of bromine in acetic acid produced 5-thiocyanato-2-sulfonamides 6. Interaction of 4 with aminoguanidine hydrochloride in ethanol produced the corresponding 5-guanylhydrazone derivatives 5. Compounds 5 and 6 showed a high degree of antibacterial activity against both Escherichia coli and Staphylococcus aureus comparable to that of sulfamethoxazole and Norfloxacin. However, they were found to show moderate activity against Salmonella typhi, Pseudomonas aeruginosa and Pneumococci. (C) 2000 Editions scientifiques et medicales Elsevier SAS.