2-[2-(3-bromophenyl)-1H-imidazol-5-yl]ethanol | 178920-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-(3-bromophenyl)-1H-imidazol-5-yl]ethanol
• CAS: 178920-25-7
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: WDUPPNINUUPEEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-(3-bromophenyl)-1H-imidazol-5-yl]ethanol 在 氯化亚砜 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-[2-(3-bromophenyl)-1H-imidazol-5-yl]-N,N-dimethylethanamine
  参考文献：
  名称：

  2-苯基组胺的Nα-烷基化衍生物：有效的组胺H1受体激动剂的合成和体外活性。

  摘要：

  已经制备了新的有效的Nα-烷基化的组胺H 1受体激动剂，并在功能上评估了部分激动剂的效力和选择性。Nα-甲基-2-（3-三氟甲基苯基）组胺收缩豚鼠的回肠段和主动脉环，相对效力分别为174％（95％confid。lim。161-188％）和217％（164-287％） ）（组胺：100％），是迄今为止描述的最有效的H1受体激动剂。

  DOI：

  10.1016/s0960-894x(98)00461-2
• 作为产物：
  描述：

  1,4-二羟基-2-丁酮 、 3-溴苯甲亚氨酸甲酯盐酸盐 在 氨 作用下， 以71%的产率得到2-[2-(3-bromophenyl)-1H-imidazol-5-yl]ethanol
  参考文献：
  名称：

  2-苯基组胺的Nα-烷基化衍生物：有效的组胺H1受体激动剂的合成和体外活性。

  摘要：

  已经制备了新的有效的Nα-烷基化的组胺H 1受体激动剂，并在功能上评估了部分激动剂的效力和选择性。Nα-甲基-2-（3-三氟甲基苯基）组胺收缩豚鼠的回肠段和主动脉环，相对效力分别为174％（95％confid。lim。161-188％）和217％（164-287％） ）（组胺：100％），是迄今为止描述的最有效的H1受体激动剂。

  DOI：

  10.1016/s0960-894x(98)00461-2

文献信息

• 2-Alkyl-substituted histamines and hydroxyethylimidazoles with G-protein-stimulatory activity
  作者：H Detert、C Leschke、W Tögel、R Seifert、W Schunacki

  DOI：10.1016/0223-5234(96)89166-5

  日期：1996.1

  Cationic-amphiphilic 2-substituted histamines activate pertussis toxin-sensitive guanine nucleotide-binding proteins (G-proteins) by a receptor-independent mechanism. From our recent studies it became apparent that lipophilicity is an important determinant for this G-protein activation, but the influence of basicity remained unknown. We prepared seven novel 2-alkyl-substituted histamines and five novel 2-alkyl-substituted hydroxyethylimidazoles and studied their effects on high-affinity guanosine triphosphate (GTP) hydrolysis in membranes of the human leukemia cell line, HL-60. 2-Octylhistamine was found to be the most effective GTPase activator among 2-substituted histamines presently available (150% stimulation above basal), and 2-tetradecylhistamine is the most potent substance in this regard (pEC(50) = 5.9). Branching of the alkyl chain and the introduction of an ether group adversely affected GTPase activation. Compared to a phenyl ring, a bulky adamantyl sphere enhanced G-protein-stimulatory activity. In the case of 2-(3-bromophenyl)histamine, 2-adamantylhistamine and 2-(3-phenylpropyl)histamine, replacement of the aminoethyl group by a hydroxyethyl group at the imidazole greatly reduced GTPase-activating properties, pointing to the importance of the basic domain in the activation process. Unexpectedly, however, in the case of a very lipophilic substituent (heptadecyl chain) the exchange of the aminoethyl group by a hydroxyethyl group had no substantial inhibitory effect, indicating that the presence of a primary amine is not a conditio sine qua non for a substance being a receptor-independent G-protein activator. Concerning histamine H-1-receptors the newly prepared compounds proved to be weak antagonists.
• Nα-alkylated derivatives of 2-phenylhistamines: Synthesis and in vitro activity of potent histamine H1-receptor agonists
  作者：K. Kramer、S. Elz、H.H. Pertz、W. Schunack

  DOI：10.1016/s0960-894x(98)00461-2

  日期：1998.9

  alpha-alkylated histamine H1-receptor agonists have been prepared and functionally evaluated for partial agonist potency and selectivity. N alpha-Methyl-2-(3-trifluoromethylphenyl)histamine contracts ileal segments and aortic rings of guinea-pig with a relative potency of 174% (95% confid. lim. 161-188%) and 217% (164-287%), respectively (histamine: 100%) and is the most potent H1 receptor agonist described

  已经制备了新的有效的Nα-烷基化的组胺H 1受体激动剂，并在功能上评估了部分激动剂的效力和选择性。Nα-甲基-2-（3-三氟甲基苯基）组胺收缩豚鼠的回肠段和主动脉环，相对效力分别为174％（95％confid。lim。161-188％）和217％（164-287％） ）（组胺：100％），是迄今为止描述的最有效的H1受体激动剂。