1-(2,4-dichlorophenyl)-2-hydroxy-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one | 134529-55-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2,4-dichlorophenyl)-2-hydroxy-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one
• 英文别名: 1-(2,4-Dichlorophenyl)-2-hydroxy-3-imidazol-1-yl-2-phenylpropan-1-one
• CAS: 134529-55-8
• 化学式: C₁₈H₁₄Cl₂N₂O₂
• 分子量: 361.227
• InChiKey: MZYZSZQULDGUQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-2-hydroxy-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one 在 (diethylamido)sulfur trifluoride 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 1-(2,4-dichlorophenyl)-2-fluoro-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one
  参考文献：
  名称：

  2-Chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one hydrochloride, a novel, nonmutagenic antibacterial with specific activity against anaerobic bacteria

  摘要：

  1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one (2) is identified as a potent antibacterial agent. A compound, 2-chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one (5) has been designed with the intention of its acting as a pro-drug, liberating the lethal species 2 specifically within the target anaerobic bacterial cell following bioreduction by bacterial ferredoxin or related electron transfer proteins. The synthesis and biological activity of 5 is described and compared with the activities of the analogous alpha-bromo ketone 6 and alpha-fluoro ketone 7. Synthesis of 6, 7, and the corresponding alpha-hydroxy ketone 11 is also described.

  DOI：

  10.1021/jm00112a006
• 作为产物：
  描述：

  alpha- 溴苯乙烯 在 sodium hydroxide 、 barium manganate 、 双氧水 、 magnesium 作用下， 以 甲醇 、 异丙醇 、 甲苯 为溶剂， 反应 17.0h， 生成 1-(2,4-dichlorophenyl)-2-hydroxy-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one
  参考文献：
  名称：

  2-Chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one hydrochloride, a novel, nonmutagenic antibacterial with specific activity against anaerobic bacteria

  摘要：

  1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one (2) is identified as a potent antibacterial agent. A compound, 2-chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one (5) has been designed with the intention of its acting as a pro-drug, liberating the lethal species 2 specifically within the target anaerobic bacterial cell following bioreduction by bacterial ferredoxin or related electron transfer proteins. The synthesis and biological activity of 5 is described and compared with the activities of the analogous alpha-bromo ketone 6 and alpha-fluoro ketone 7. Synthesis of 6, 7, and the corresponding alpha-hydroxy ketone 11 is also described.

  DOI：

  10.1021/jm00112a006

文献信息

• 2-Chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one hydrochloride, a novel, nonmutagenic antibacterial with specific activity against anaerobic bacteria
  作者：Jon P. Dickens、George J. Ellames、Nigel J. Hare、Kevin R. Lawson、William R. McKay、Anthony P. Metters、Peter L. Myers、Anthony M. S. Pope、Roger M. Upton

  DOI：10.1021/jm00112a006

  日期：1991.8

  1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one (2) is identified as a potent antibacterial agent. A compound, 2-chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan-1-one (5) has been designed with the intention of its acting as a pro-drug, liberating the lethal species 2 specifically within the target anaerobic bacterial cell following bioreduction by bacterial ferredoxin or related electron transfer proteins. The synthesis and biological activity of 5 is described and compared with the activities of the analogous alpha-bromo ketone 6 and alpha-fluoro ketone 7. Synthesis of 6, 7, and the corresponding alpha-hydroxy ketone 11 is also described.