2-(2-Adamantan-1-yl-1H-imidazol-4-yl)-ethanol | 178920-27-9

• 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-Adamantan-1-yl-1H-imidazol-4-yl)-ethanol
• 英文别名: 2-[2-(1-adamantyl)-1H-imidazol-5-yl]ethanol
• CAS: 178920-27-9
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: HGLXQMDLZSBBDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 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-Adamantan-1-yl-1H-imidazol-4-yl)-ethanol 在 盐酸 、 氯化亚砜 、 氨 作用下， 反应 51.17h， 生成 2-(2-Adamantan-1-yl-1H-imidazol-4-yl)-ethylamine
  参考文献：
  名称：

  2-Alkyl-substituted histamines and hydroxyethylimidazoles with G-protein-stimulatory activity

  摘要：

  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.

  DOI：

  10.1016/0223-5234(96)89166-5
• 作为产物：
  描述：

  1,4-二羟基-2-丁酮 、 adamantane-1-carboximidic acid methyl ester; hydrochloride 在 氨 作用下， 以49%的产率得到2-(2-Adamantan-1-yl-1H-imidazol-4-yl)-ethanol
  参考文献：
  名称：

  2-Alkyl-substituted histamines and hydroxyethylimidazoles with G-protein-stimulatory activity

  摘要：

  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.

  DOI：

  10.1016/0223-5234(96)89166-5