Toluene-4-sulfonate2-((E)-2-{4-[(4-amino-benzoyl)-hydrazonomethyl]-phenyl}-vinyl)-1,3-dimethyl-3H-imidazol-1-ium; | 123508-47-4

• 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: Toluene-4-sulfonate2-((E)-2-{4-[(4-amino-benzoyl)-hydrazonomethyl]-phenyl}-vinyl)-1,3-dimethyl-3H-imidazol-1-ium
• 英文别名: 4-amino-N-[[4-[2-(1,3-dimethylimidazol-1-ium-2-yl)ethenyl]phenyl]methylideneamino]benzamide;4-methylbenzenesulfonate
• CAS: 123508-47-4
• 化学式: C₇H₇O₃S*C₂₁H₂₂N₅O
• 分子量: 531.635
• InChiKey: IRAUZVNTDOTRPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Toluene-4-sulfonate2-[(E)-2-(4-formyl-phenyl)-vinyl]-1,3-dimethyl-3H-imidazol-1-ium; 、 4-氨基苯甲酰肼 以 乙醇 为溶剂， 反应 4.0h， 生成 Toluene-4-sulfonate2-((E)-2-{4-[(4-amino-benzoyl)-hydrazonomethyl]-phenyl}-vinyl)-1,3-dimethyl-3H-imidazol-1-ium;
  参考文献：
  名称：

  Cationic antiprotozoal drugs. Trypanocidal activity of 2-(4'-formylphenyl)imidazo[1,2-a]pyridinium guanylhydrazones and related derivatives of quaternary heteroaromatic compounds

  摘要：

  A series of quaternary 2-phenylimidazo[1,2-a]pyridinum salts has been prepared and evaluated for antiparasitic activity. Primary attention was focused on derivatives with amido, substituted hydrazone, and heterocyclic functionality at the para position of the phenyl substituent. Guanylhydrazones and N-substituted guanylhydrazones of the 4'-formyl-substituted compounds are very active against the blood state Trypanosoma rhodesiense in mice by subcutaneous or oral administration. The most potent compounds attain 100% survival for 30 days at doses of less than 1.0 mg/kg (sc) and greater than 5.0 mg/kg (po). Weaker activity is noted for certain other 4'-substituents such as carboxamidines and carboxamide oximes. Considerable variation in structure, including replacing of the imidazo [1,2-a]pyridinium ring by other cationic heterocyclic rings and insertion of linking groups between the heterocyclic ring and phenyl group, can be done, and a high level of activity is maintained. Relationships between these structural changes and biological activity are discussed.

  DOI：

  10.1021/jm00163a049

文献信息

• Cationic antiprotozoal drugs. Trypanocidal activity of 2-(4'-formylphenyl)imidazo[1,2-a]pyridinium guanylhydrazones and related derivatives of quaternary heteroaromatic compounds
  作者：Richard J. Sundberg、Daniel J. Dahlhausen、G. Manikumar、B. Mavunkel、A. Biswas、V. Srinivasan、H. A. Musallam、Willis A. Reid、Arba L. Ager

  DOI：10.1021/jm00163a049

  日期：1990.1

  A series of quaternary 2-phenylimidazo[1,2-a]pyridinum salts has been prepared and evaluated for antiparasitic activity. Primary attention was focused on derivatives with amido, substituted hydrazone, and heterocyclic functionality at the para position of the phenyl substituent. Guanylhydrazones and N-substituted guanylhydrazones of the 4'-formyl-substituted compounds are very active against the blood state Trypanosoma rhodesiense in mice by subcutaneous or oral administration. The most potent compounds attain 100% survival for 30 days at doses of less than 1.0 mg/kg (sc) and greater than 5.0 mg/kg (po). Weaker activity is noted for certain other 4'-substituents such as carboxamidines and carboxamide oximes. Considerable variation in structure, including replacing of the imidazo [1,2-a]pyridinium ring by other cationic heterocyclic rings and insertion of linking groups between the heterocyclic ring and phenyl group, can be done, and a high level of activity is maintained. Relationships between these structural changes and biological activity are discussed.