4-(2-bromoethyl)-5-methyl-1H-imidazole hydrobromide | 126377-38-6

• 英文名称: 4-(2-bromoethyl)-5-methyl-1H-imidazole hydrobromide
• 英文别名: 4-(2-bromoethyl)-5-methyl-1H-imidazole;hydrobromide
• CAS: 126377-38-6
• 化学式: BrH*C₆H₉BrN₂
• 分子量: 269.967
• InChiKey: UDTHXHXHQDSIAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(2-bromoethyl)-5-methyl-1H-imidazole hydrobromide 在 N,N'-羰基二咪唑 作用下， 以 乙醇 为溶剂， 反应 17.5h， 生成 N-(2-{[2-(5-methyl-1H-imidazol-4-yl)ethyl]amino}ethyl)pyridine-4-carboxamide
  参考文献：
  名称：

  Cardiotonic agents. 6. Histamine analogs as potential cardiovascular selective H2 agonists

  摘要：

  Twenty-six alkyl and aralkyl histamine analogues were prepared as potential cardiotonic agents. Compounds were designed to allow interaction with a putative secondary aryl binding site at the H2 receptor, the presence of which was inferred from the structure of cyprohepatadine, which is known to have H2-antagonist properties. The compounds were examined for inotropic activity in ferret papillary muscle. Potent inotropic activity was generally found in N-alkyl- and N,N-dialkylimidazole-4-ethanamines, whereas N-(amidoalkyl)imidazole-4-ethanamines and N-alkylimidazole-4-propanamines were at best weakly active. Five compounds were examined in screens designed to assess hemodynamic effects and gastric acid secretion in vivo. Two of these compounds, alpha-(3-phenyl-2-transpropenyl)-1H-imidazole-4-ethanamine and N-heptyl-1H-imidazole-4-ethanamine, showed positive inotropic activity with minimal effects on heart rate and mean arterial pressure in vivo; however, both compounds were found to stimulate gastric acid secretion. These results demonstrate that selectivity between various H2-receptor-mediated activities can be obtained with substituted histamine analogues.

  DOI：

  10.1021/jm00168a024
• 作为产物：
  描述：

  5(4)-methyl-4(5)-(2-hydroxyethyl)imidazole 在 氢溴酸 作用下， 反应 96.0h， 以51%的产率得到4-(2-bromoethyl)-5-methyl-1H-imidazole hydrobromide
  参考文献：
  名称：

  Cardiotonic agents. 6. Histamine analogs as potential cardiovascular selective H2 agonists

  摘要：

  Twenty-six alkyl and aralkyl histamine analogues were prepared as potential cardiotonic agents. Compounds were designed to allow interaction with a putative secondary aryl binding site at the H2 receptor, the presence of which was inferred from the structure of cyprohepatadine, which is known to have H2-antagonist properties. The compounds were examined for inotropic activity in ferret papillary muscle. Potent inotropic activity was generally found in N-alkyl- and N,N-dialkylimidazole-4-ethanamines, whereas N-(amidoalkyl)imidazole-4-ethanamines and N-alkylimidazole-4-propanamines were at best weakly active. Five compounds were examined in screens designed to assess hemodynamic effects and gastric acid secretion in vivo. Two of these compounds, alpha-(3-phenyl-2-transpropenyl)-1H-imidazole-4-ethanamine and N-heptyl-1H-imidazole-4-ethanamine, showed positive inotropic activity with minimal effects on heart rate and mean arterial pressure in vivo; however, both compounds were found to stimulate gastric acid secretion. These results demonstrate that selectivity between various H2-receptor-mediated activities can be obtained with substituted histamine analogues.

  DOI：

  10.1021/jm00168a024

文献信息

• LAMPE, JOHN W.;HANNA, REDA G.;PISCITELLI, THOMAS A.;CHOU, YUO-LING;ERHARD+, J. MED. CHEM., 33,(1990) N, C. 1688-1697
  作者：LAMPE, JOHN W.、HANNA, REDA G.、PISCITELLI, THOMAS A.、CHOU, YUO-LING、ERHARD+

  DOI：——

  日期：——