3-[2-(4-甲氧基苯基)乙基]-1H-咪唑-2-硫酮 | 100134-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-[2-(4-甲氧基苯基)乙基]-1H-咪唑-2-硫酮
• 英文名称: 1-(4-methoxy-phenethyl)-1,3-dihydro-imidazole-2-thione
• 英文别名: 1-(4-Methoxy-phenaethyl)-1,3-dihydro-imidazol-2-thion；2H-Imidazole-2-thione, 1,3-dihydro-1-[2-(4-methoxyphenyl)ethyl]-；3-[2-(4-methoxyphenyl)ethyl]-1H-imidazole-2-thione
• CAS: 100134-69-8
• 化学式: C₁₂H₁₄N₂OS
• mdl: MFCD10692754
• 分子量: 234.322
• InChiKey: HLGQEPDUWMDPKD-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  367.3±44.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[2-(4-甲氧基苯基)乙基]-1H-咪唑-2-硫酮 在 乙醇 、 镍 作用下， 生成 1-(4-methoxy-phenethyl)-1H-imidazole
  参考文献：
  名称：

  Studies of Imidazoles. VII. Substituted 1-Phenethylimidazoles and Related Compounds^*,1

  摘要：

  DOI：

  10.1021/jo01362a008
• 作为产物：
  描述：

  4-甲氧基苯乙酰氯 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 3-[2-(4-甲氧基苯基)乙基]-1H-咪唑-2-硫酮
  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

• Studies of Imidazoles. VII. Substituted 1-Phenethylimidazoles and Related Compounds^*,1
  作者：W. N. CANNON、C. E. POWELL、R. G. JONES

  DOI：10.1021/jo01362a008

  日期：1957.11
• 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.