5-(12-chlorododecyl)imidazole-1-sulfonic acid dimethylamide | 645392-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(12-chlorododecyl)imidazole-1-sulfonic acid dimethylamide
• 英文别名: 5-(12-chlorododecyl)-N,N-dimethylimidazole-1-sulfonamide
• CAS: 645392-48-9
• 化学式: C₁₇H₃₂ClN₃O₂S
• 分子量: 377.979
• InChiKey: CSYPUVRQNQYOPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(12-chlorododecyl)imidazole-1-sulfonic acid dimethylamide 在 氢溴酸 、 sodium carbonate 、 一水合肼 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 VUF 5671
  参考文献：
  名称：

  Synthesis and Pharmacological Identification of Neutral Histamine H₁-Receptor Antagonists

  摘要：

  In the present study we searched for neutral antagonists for the human histamine H-1-receptor (H,R) by screening newly synthesized ligands that are structurally related to H1R agonists for their affinity using radioligand displacement studies and by assessing their functional activity via performing a NF-kappaB driven reporter-gene assay that allows for the detection of both agonistic and inverse agonistic responses. Starting from the endogenous agonist for the H1R, histamine, we synthesized and tested various analogues and ultimately identified several compounds with partial inverse agonistic properties and two neutral Hi-receptor antagonists, namely 2-[2-(4,4diphenylbutyl)-1H-imidazol-4-yl]ethylamine (histabudifen, 18d) (pK(i) = 5.8, alpha = 0.02) and 2-[2-(5,5-diphenylpentyl)-1H-imidazol-4-yl]ethylamine (histapendifen, 18e) (pK(i) = 5.9, alpha = -0.09).

  DOI：

  10.1021/jm030936t
• 作为产物：
  描述：

  1-chloro-12-iodododecane 、 N,N-二甲基咪唑-1-磺酰胺 、 叔丁基二甲基氯硅烷 生成 5-(tert-butyl-dimethylsilanyl)imidazole-1-sulfonic acid dimethylamide 、 5-(12-chlorododecyl)imidazole-1-sulfonic acid dimethylamide
  参考文献：
  名称：

  Synthesis and Pharmacological Identification of Neutral Histamine H₁-Receptor Antagonists

  摘要：

  In the present study we searched for neutral antagonists for the human histamine H-1-receptor (H,R) by screening newly synthesized ligands that are structurally related to H1R agonists for their affinity using radioligand displacement studies and by assessing their functional activity via performing a NF-kappaB driven reporter-gene assay that allows for the detection of both agonistic and inverse agonistic responses. Starting from the endogenous agonist for the H1R, histamine, we synthesized and tested various analogues and ultimately identified several compounds with partial inverse agonistic properties and two neutral Hi-receptor antagonists, namely 2-[2-(4,4diphenylbutyl)-1H-imidazol-4-yl]ethylamine (histabudifen, 18d) (pK(i) = 5.8, alpha = 0.02) and 2-[2-(5,5-diphenylpentyl)-1H-imidazol-4-yl]ethylamine (histapendifen, 18e) (pK(i) = 5.9, alpha = -0.09).

  DOI：

  10.1021/jm030936t