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

• 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: 1-[3-(4-Nitrophenoxy)-3-phenyl-propyl]imidazole
• 英文别名: 1-[3-(4-nitrophenoxy)-3-phenylpropyl]imidazole
• 化学式: C₁₈H₁₇N₃O₃
• 分子量: 323.351
• InChiKey: MWCAASWKRSZOFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 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：
  72.9
• 氢给体数：
  0
• 氢受体数：
  4

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-Nitrophenoxy)-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

• Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents
  作者：Kalpana Bhandari、Nagarapu Srinivas、Vijay K. Marrapu、Aditya Verma、Saumya Srivastava、Suman Gupta

  DOI：10.1016/j.bmcl.2009.10.117

  日期：2010.1

  A series of aryloxy alkyl/aryl alkyl imidazoles were synthesized and evaluated in vitro as antileishmanials against Leishmania donovani. All the 19 compounds exhibited 94–100% inhibition at 10 μg/mL against promastigotes and 12 compounds exhibited high inhibition with an IC50 in the range of 0.47–4.85 μg/mL against amastigotes. Promising compounds were tested further in vivo. Among all, compounds 4

  合成了一系列芳氧基烷基/芳基烷基咪唑，并作为抗利什曼原虫的体外抗疟药进行了体外评估。所有19种化合物在10μg/ mL的浓度下对前鞭毛体均表现出94-100％的抑制作用，而12种化合物在对amastigotes的IC 50为0.47-4.85μg/ mL时表现出高抑制性。有希望的化合物在体内进行了进一步测试。在所有化合物中，具有4-CF 3芳氧基部分的化合物4和23在体内对培养基的抑制作用为58–60％，从而为抗疟药提供了新的结构线索。