3-Methyl-2-(2-phenylethyl)imidazol-4-amine | 145798-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methyl-2-(2-phenylethyl)imidazol-4-amine
• CAS: 145798-99-8
• 化学式: C₁₂H₁₅N₃
• 分子量: 201.271
• InChiKey: UAVLHLYBTDUJMW-UHFFFAOYSA-N

物化性质

• 沸点：
  425.7±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-methyl-5-nitro-2-[(E)-2-phenylvinyl]-1H-imidazole 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 生成 3-Methyl-2-(2-phenylethyl)imidazol-4-amine
  参考文献：
  名称：

  Synthesis and Electrochemistry of 2-Ethenyl and 2-Ethanyl Derivatives of 5-Nitroimidazole and Antimicrobial Activity against Giardia lamblia

  摘要：

  Infections with the diarrheagenic pathogen, Giardia lamblia, are commonly treated with the 5-nitroimidazole (5-NI) metronidazole (Mz), and yet treatment failures and Mz resistance occur. Using a panel of new 2-ethenyl and 2-ethanyl 5-NI derivatives, we found that compounds with a saturated bridge between the 5-NI core and a pendant ring system exhibited only modestly increased antigiardial activity and could not overcome Mz resistance. By contrast, olefins with a conjugated bridge connecting the core and a substituted phenyl or heterocyclic ring showed greatly increased antigiardial activity without toxicity, and several overcame Mz resistance and were more effective than Mz in a murine giardiasis model. Determination of the half-wave potential of the initial one-electron transfer by cyclic voltammetry revealed that easier redox activation correlated with greater antigiardial activity and capacity to overcome Mz resistance. These studies show the potential of combining systematic synthetic approaches with biological and electrochemical evaluations in developing improved 5-NI drugs.

  DOI：

  10.1021/jm900356n

文献信息

• Al-Shaar, Adnan H. M.; Gilmour, David W.; Lythgoe, David J., Journal of the Chemical Society. Perkin transactions I, 1992, # 21, p. 2779 - 2788
  作者：Al-Shaar, Adnan H. M.、Gilmour, David W.、Lythgoe, David J.、McClenaghan, Ian、Ramsden, Christopher A.

  DOI：——

  日期：——