1-[2-Biphenyl-4-yl-1-(4-methoxy-benzyl)-ethyl]-1H-imidazole

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-[2-Biphenyl-4-yl-1-(4-methoxy-benzyl)-ethyl]-1H-imidazole
• 英文别名: 1-[1-[(4-Methoxyphenyl)methyl]-2-(4-phenylphenyl)ethyl]imidazole；1-[1-(4-methoxyphenyl)-3-(4-phenylphenyl)propan-2-yl]imidazole
• 化学式: C₂₅H₂₄N₂O
• 分子量: 368.478
• InChiKey: SDAWROHZJFECJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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-Biphenyl-4-yl-2-imidazol-1-yl-3-(4-methoxy-phenyl)-propan-1-one 在 氢氧化钾 、 一水合肼 作用下， 以 乙二醇 为溶剂， 反应 3.0h， 生成 1-[2-Biphenyl-4-yl-1-(4-methoxy-benzyl)-ethyl]-1H-imidazole
  参考文献：
  名称：

  Synthesis and antimicrobial properties of 3-aryl-1-(1,1′-biphenyl-4-yl)-2-(1H-imidazol-1-yl)propanes as ‘carba-analogues’ of the N-arylmethyl-N-[(1,1′-biphenyl)-4-ylmethyl])-1H-imidazol-1-amines, a new class of antifungal agents

  摘要：

  A new series of 3-phenyl-1-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-yl)propane derivatives 2a-l (related to the antifungal bifonazole) was synthesized and tested for antimicrobial activity. A number of substituents on the phenyl ring were chosen to compare the relative biological properties with those of corresponding aza-analogues, previously described by us. The in vitro antifungal activities of the newly synthesized azoles were tested against several pathogenic fungi responsible for human disease. Test pathogens included representatives of yeasts (Candida albicans, Candida parapsilosis, Criptococcus neoformans), dermathophytes (Tricophyton verrucosum, Tricophyton rubrum, Microsporum gypseum) and moulds (Aspergillus fumigatus). Bifonazole and miconazole were used as reference drugs. Title compounds were prepared by alkylation of 1-biphenyl-4-yl-2-imidazol-1-yl-ethanone with the proper arylmethyl halide and subsequent reduction of corresponding ketones applying the Huang-Minlon modification of the Wolff-Kishner reaction.

  DOI：

  10.1016/s0014-827x(03)00094-6

文献信息

• Synthesis and antimicrobial properties of 3-aryl-1-(1,1′-biphenyl-4-yl)-2-(1H-imidazol-1-yl)propanes as ‘carba-analogues’ of the N-arylmethyl-N-[(1,1′-biphenyl)-4-ylmethyl])-1H-imidazol-1-amines, a new class of antifungal agents
  作者：Sabrina Castellano、Giorgio Stefancich、Annalisa Chillotti、Graziella Poni

  DOI：10.1016/s0014-827x(03)00094-6

  日期：2003.8

  A new series of 3-phenyl-1-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-yl)propane derivatives 2a-l (related to the antifungal bifonazole) was synthesized and tested for antimicrobial activity. A number of substituents on the phenyl ring were chosen to compare the relative biological properties with those of corresponding aza-analogues, previously described by us. The in vitro antifungal activities of the newly synthesized azoles were tested against several pathogenic fungi responsible for human disease. Test pathogens included representatives of yeasts (Candida albicans, Candida parapsilosis, Criptococcus neoformans), dermathophytes (Tricophyton verrucosum, Tricophyton rubrum, Microsporum gypseum) and moulds (Aspergillus fumigatus). Bifonazole and miconazole were used as reference drugs. Title compounds were prepared by alkylation of 1-biphenyl-4-yl-2-imidazol-1-yl-ethanone with the proper arylmethyl halide and subsequent reduction of corresponding ketones applying the Huang-Minlon modification of the Wolff-Kishner reaction.