1-[3-(4-Methylphenoxy)-3-phenyl-propyl]imidazole

• 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-(4-Methylphenoxy)-3-phenyl-propyl]imidazole
• 英文别名: 1-[3-(4-methylphenoxy)-3-phenylpropyl]imidazole
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: JOGOREDHESCZMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (1-溴-3-氯丙基)苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 84.5h， 生成 1-[3-(4-Methylphenoxy)-3-phenyl-propyl]imidazole
  参考文献：
  名称：

  Imidazole Analogues of Fluoxetine, a Novel Class of Anti-Candida Agents

  摘要：

  Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-1-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH3 > NO2 > CF3).

  DOI：

  10.1021/jm049856v

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.
• Imidazole Analogues of Fluoxetine, a Novel Class of Anti-<i>Candida</i> Agents
  作者：Romano Silvestri、Marino Artico、Giuseppe La Regina、Alessandra Di Pasquali、Gabriella De Martino、Felicia Diodata D'Auria、Lucia Nencioni、Anna Teresa Palamara

  DOI：10.1021/jm049856v

  日期：2004.7.1

  Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-1-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH3 > NO2 > CF3).