Imidazol-1-yl-thiophen-2-ylmethyl-amine | 308288-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Imidazol-1-yl-thiophen-2-ylmethyl-amine
• 英文别名: N-(2-thienylmethyl)imidazol-1-amine；N-(thiophen-2-ylmethyl)imidazol-1-amine
• CAS: 308288-14-4
• 化学式: C₈H₉N₃S
• 分子量: 179.246
• InChiKey: OLFNZXPTAJCIQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-叔丁基苄溴 、 Imidazol-1-yl-thiophen-2-ylmethyl-amine 在 18-冠醚-6 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 4.25h， 以49%的产率得到(4-tert-Butyl-benzyl)-imidazol-1-yl-thiophen-2-ylmethyl-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：

  Imidazol-1-yl-[1-thiophen-2-yl-meth-(E)-ylidene]-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以100%的产率得到Imidazol-1-yl-thiophen-2-ylmethyl-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.