N-[(2,4-dichlorophenyl)methyl]-1,2,4-triazol-4-amine | 308288-18-8

• 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-[(2,4-dichlorophenyl)methyl]-1,2,4-triazol-4-amine
• CAS: 308288-18-8
• 化学式: C₉H₈Cl₂N₄
• 分子量: 243.095
• InChiKey: XFHSBTXBXLFGSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cinnamyl bromide 、 N-[(2,4-dichlorophenyl)methyl]-1,2,4-triazol-4-amine 在 四丁基硫酸氢铵 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到N-[(E)-cinnamyl]-N-[(2,4-dichlorophenyl)methyl]-1,2,4-triazol-4-amine
  参考文献：
  名称：

  A New Class of Antifungal Agents. Synthesis and Antimycotic Activity of DisubstitutedN-Azolylamines

  摘要：

  In this study we extended our exploration of the N-azolylamine moiety for its antifungal activity. We prepared a number of N-azolylamino derivatives. The synthetic sequence includes the preparation of aminoazole Schiff bases, and the reduction and the alkylation of the corresponding secondary amines. The title compounds were evaluated in vitro against several pathogenic fungi responsible for human disease. The most potent antimicrobial compound was the N-(biphenyl-4-yl)methyl-N-(2,4-dichlorophenyl)methyl-1H-imidazol-1-ylamine (21), which was found to be active against yeasts and dermatophytes; its potency and selectivity were comparable to those of miconazole.

  DOI：

  10.1002/1521-4184(20009)333:9<299::aid-ardp299>3.0.co;2-f
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 sodium tetrahydroborate 、 碳酸氢钠 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 水 为溶剂， 反应 47.0h， 生成 N-[(2,4-dichlorophenyl)methyl]-1,2,4-triazol-4-amine
  参考文献：
  名称：

  A New Class of Antifungal Agents. Synthesis and Antimycotic Activity of DisubstitutedN-Azolylamines

  摘要：

  In this study we extended our exploration of the N-azolylamine moiety for its antifungal activity. We prepared a number of N-azolylamino derivatives. The synthetic sequence includes the preparation of aminoazole Schiff bases, and the reduction and the alkylation of the corresponding secondary amines. The title compounds were evaluated in vitro against several pathogenic fungi responsible for human disease. The most potent antimicrobial compound was the N-(biphenyl-4-yl)methyl-N-(2,4-dichlorophenyl)methyl-1H-imidazol-1-ylamine (21), which was found to be active against yeasts and dermatophytes; its potency and selectivity were comparable to those of miconazole.

  DOI：

  10.1002/1521-4184(20009)333:9<299::aid-ardp299>3.0.co;2-f

文献信息

• A New Class of Antifungal Agents. Synthesis and Antimycotic Activity of DisubstitutedN-Azolylamines
  作者：Sabrina Castellano、Giorgio Stefancich、Chiara Musiu、Paolo La Colla

  DOI：10.1002/1521-4184(20009)333:9<299::aid-ardp299>3.0.co;2-f

  日期：2000.9

  In this study we extended our exploration of the N-azolylamine moiety for its antifungal activity. We prepared a number of N-azolylamino derivatives. The synthetic sequence includes the preparation of aminoazole Schiff bases, and the reduction and the alkylation of the corresponding secondary amines. The title compounds were evaluated in vitro against several pathogenic fungi responsible for human disease. The most potent antimicrobial compound was the N-(biphenyl-4-yl)methyl-N-(2,4-dichlorophenyl)methyl-1H-imidazol-1-ylamine (21), which was found to be active against yeasts and dermatophytes; its potency and selectivity were comparable to those of miconazole.