3-[4-(4-hydroxyphenyl)butyl]-1H-imidazole-2-thione | 95333-55-4

• 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: 3-[4-(4-hydroxyphenyl)butyl]-1H-imidazole-2-thione
• CAS: 95333-55-4
• 化学式: C₁₃H₁₆N₂OS
• 分子量: 248.349
• InChiKey: MHGCNYZQMMAZMH-UHFFFAOYSA-N

物化性质

• 沸点：
  421.6±47.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-[4-(4-甲氧基-苯基)-丁基]-1,3-二氢-咪唑-2-硫酮 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-[4-(4-hydroxyphenyl)butyl]-1H-imidazole-2-thione
  参考文献：
  名称：

  Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione

  摘要：

  The synthesis and characterization of some 1-(phenylalkyl)imidazole-2-thiones as a novel class of "multisubstrate" inhibitors of dopamine beta-hydroxylase (DBH) are described. These inhibitors incorporate structural features that resemble both tyramine and oxygen substrates, and as evidenced by steady-state kinetics, they appear to bind both the phenethylamine binding site and the active site copper atom(s) in DBH. A series of structural congeners that incorporate different bridging chain lengths between the phenyl ring (dopamine mimic) and the imidazole-2-thione group (oxygen mimic) define the optimum distance for inhibitory potency and the likely intersite distance in the DBH active site. Additional bridging analogues were prepared to determine the active site bulk tolerance and the effects of heteroatom replacement.

  DOI：

  10.1021/jm00162a008

文献信息

• Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione
  作者：Lawrence I. Kruse、Carl Kaiser、Walter E. DeWolf、James S. Frazee、Eleanor Garvey、Eileen L. Hilbert、Wayne A. Faulkner、Kathryn E. Flaim、John L. Sawyer、Barry A. Berkowitz

  DOI：10.1021/jm00162a008

  日期：1986.12

  The synthesis and characterization of some 1-(phenylalkyl)imidazole-2-thiones as a novel class of "multisubstrate" inhibitors of dopamine beta-hydroxylase (DBH) are described. These inhibitors incorporate structural features that resemble both tyramine and oxygen substrates, and as evidenced by steady-state kinetics, they appear to bind both the phenethylamine binding site and the active site copper atom(s) in DBH. A series of structural congeners that incorporate different bridging chain lengths between the phenyl ring (dopamine mimic) and the imidazole-2-thione group (oxygen mimic) define the optimum distance for inhibitory potency and the likely intersite distance in the DBH active site. Additional bridging analogues were prepared to determine the active site bulk tolerance and the effects of heteroatom replacement.