1-(3-phenoxy-3-phenylpropyl)-1H-imidazole | 1037716-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-phenoxy-3-phenylpropyl)-1H-imidazole
• 英文别名: 1-(3-Phenoxy-3-phenyl-propyl)imidazole；1-(3-phenoxy-3-phenylpropyl)imidazole
• CAS: 1037716-35-0
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: MLPKGIWIMKQFNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  咪唑 、 (3-氯-1-苯氧基丙基)苯 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以59%的产率得到1-(3-phenoxy-3-phenylpropyl)-1H-imidazole
  参考文献：
  名称：

  1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies

  摘要：

  New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 mu g/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC <= 5 mu g/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents.

  DOI：

  10.1021/jm800009r

文献信息

• 1-[(3-Aryloxy-3-aryl)propyl]-1<i>H</i>-imidazoles, New Imidazoles with Potent Activity against<i>Candida albicans</i>and Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies
  作者：Giuseppe La Regina、Felicia Diodata D’Auria、Andrea Tafi、Francesco Piscitelli、Stefania Olla、Fabiana Caporuscio、Lucia Nencioni、Roberto Cirilli、Francesco La Torre、Nadja Rodrigues De Melo、Steven L. Kelly、David C. Lamb、Marino Artico、Maurizio Botta、Anna Teresa Palamara、Romano Silvestri

  DOI：10.1021/jm800009r

  日期：2008.7

  New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 mu g/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC <= 5 mu g/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents.