1-[2-(4-chlorobenzyloxy)phenyl]-2-(1H-imidazol-1-yl)ethanone | 1353432-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-(4-chlorobenzyloxy)phenyl]-2-(1H-imidazol-1-yl)ethanone
• CAS: 1353432-33-3
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: IMKSDLCBOHQMAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[2-(4-chlorobenzyloxy)phenyl]-2-(1H-imidazol-1-yl)ethanone 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 1-[2-(4-chlorobenzyloxy)phenyl]-2-(1H-imidazol-1-yl)ethanone hydrochloride
  参考文献：
  名称：

  Synthesis and Antifungal Activity of 1-[(2-Benzyloxy)Phenyl]-2-(Azol-1-yl)Ethanone Derivatives: Exploring the Scaffold Flexibility

  摘要：

  Based on the N‐(phenethyl)azole backbone of azole antifungals, we designed 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3, containing benzyloxyphenyl scaffold of croconazole. Also these compounds can be considered as flexible analogs, resulted from C2–C3 disconnection of 3′‐chloro‐3‐imidazolylflavanone 1, recently described as antifungal agent. Thus, in this report, we describe the synthesis of 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3 and their biological evaluation against different pathogenic fungi. By comparing the antifungal activity profile of flexible compounds 2 and 3 with that of rigid analog 1, it can be inferred that lower susceptibilities (higher minimum inhibitory concentrations) were observed with flexible compounds. However, among the synthesized compounds, 1‐[2‐(2,4‐dichlorobenzyloxy)phenyl]‐2‐(1H‐imidazol‐1‐yl)ethanone hydrochloride (2g) showed comparable or more potent antifungal activity in comparison with fluconazole as a standard drug.

  DOI：

  10.1111/j.1747-0285.2011.01243.x
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 potassium carbonate 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 29.0h， 生成 1-[2-(4-chlorobenzyloxy)phenyl]-2-(1H-imidazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis and Antifungal Activity of 1-[(2-Benzyloxy)Phenyl]-2-(Azol-1-yl)Ethanone Derivatives: Exploring the Scaffold Flexibility

  摘要：

  Based on the N‐(phenethyl)azole backbone of azole antifungals, we designed 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3, containing benzyloxyphenyl scaffold of croconazole. Also these compounds can be considered as flexible analogs, resulted from C2–C3 disconnection of 3′‐chloro‐3‐imidazolylflavanone 1, recently described as antifungal agent. Thus, in this report, we describe the synthesis of 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3 and their biological evaluation against different pathogenic fungi. By comparing the antifungal activity profile of flexible compounds 2 and 3 with that of rigid analog 1, it can be inferred that lower susceptibilities (higher minimum inhibitory concentrations) were observed with flexible compounds. However, among the synthesized compounds, 1‐[2‐(2,4‐dichlorobenzyloxy)phenyl]‐2‐(1H‐imidazol‐1‐yl)ethanone hydrochloride (2g) showed comparable or more potent antifungal activity in comparison with fluconazole as a standard drug.

  DOI：

  10.1111/j.1747-0285.2011.01243.x