1-(N,N-dimethylsulfamoyl)-5-(8-aminooctyl)imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(N,N-dimethylsulfamoyl)-5-(8-aminooctyl)imidazole
• 英文别名: 5-(8-aminooctyl)-N,N-dimethylimidazole-1-sulfonamide
• 化学式: C₁₃H₂₆N₄O₂S
• 分子量: 302.441
• InChiKey: DESCWWRYEFBJMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(叔丁氧基羰基)磺酰氯 、 1-(N,N-dimethylsulfamoyl)-5-(8-aminooctyl)imidazole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  组胺同源物的4-氯苄基磺酰胺和磺酰胺衍生物：有效的组胺H3受体拮抗剂的设计。

  摘要：

  制备了组胺同源物的4-氯苯基甲磺酰胺和（4-氯苄基）磺酰胺衍生物，发现它们是有效的和选择性的组胺H3受体拮抗剂。使用咪唑-4-基丁基类似物可实现高受体亲和力和低生物测定数据差异。

  DOI：

  10.1016/s0960-894x(99)00535-1
• 作为产物：
  描述：

  1-(N,N-dimethylsulfamoyl)-5-(8-phthalimidooctyl)imidazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以98%的产率得到1-(N,N-dimethylsulfamoyl)-5-(8-aminooctyl)imidazole
  参考文献：
  名称：

  Homologs of Histamine as Histamine H3 Receptor Antagonists: A New Potent and Selective H3 Antagonist, 4(5)-(5-Aminopentyl)-1H-imidazole

  摘要：

  The influence of alkyl chain length variation on the histamine H-3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(omega-aminoalkyl)-1H-imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the H-3 activity, the affinities of these compounds for the H-1 and H-2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H-3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-imidazole (impentamine, 1e) is the most potent and selective H-3 antagonist from this series of 4(5)-(omega-aminoalkyl)-1H-imidazoles 1, with a pA(2) value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed.

  DOI：

  10.1021/jm00002a008

文献信息

• US6080871A
  申请人：——

  公开号：US6080871A

  公开（公告）日：2000-06-27
• 4-Chlorobenzyl sulfonamide and sulfamide derivatives of histamine homologues: The design of potent histamine H3 receptor antagonists
  作者：Matthew J. Tozer、Ildiko M. Buck、Tracey Cooke、S.Barret Kalindjian、Iain M. McDonald、Michael J. Pether、Katherine I.M. Steel

  DOI：10.1016/s0960-894x(99)00535-1

  日期：1999.11

  4-Chlorophenylmethanesulfonamide and (4-chlorobenzyl)sulfamide derivatives of histamine homologues were prepared and found to be potent and selective histamine H3 receptor antagonists. High receptor affinity and low differences in the data from the bioassays were achieved with the imidazol-4-ylbutyl analogues.

  制备了组胺同源物的4-氯苯基甲磺酰胺和（4-氯苄基）磺酰胺衍生物，发现它们是有效的和选择性的组胺H3受体拮抗剂。使用咪唑-4-基丁基类似物可实现高受体亲和力和低生物测定数据差异。
• Homologs of Histamine as Histamine H3 Receptor Antagonists: A New Potent and Selective H3 Antagonist, 4(5)-(5-Aminopentyl)-1H-imidazole
  作者：Roeland C. Vollinga、Wiro M. P. B. Menge、Rob Leurs、Hendrik Timmerman

  DOI：10.1021/jm00002a008

  日期：1995.1

  The influence of alkyl chain length variation on the histamine H-3 receptor activity of histamine homologs 1 was investigated. A series of 4(5)-(omega-aminoalkyl)-1H-imidazoles 1 was prepared with an alkyl chain length varying from one methylene group to 10 methylene groups. Besides the H-3 activity, the affinities of these compounds for the H-1 and H-2 receptors were determined. The ethylene chain of histamine is optimal for agonistic activity on all three histamine receptor subtypes. For the H-3 receptor, elongation of the alkyl chain from three methylene groups on leads to compounds with antagonistic properties. 4(5)-(5-Aminopentyl)-1H-imidazole (impentamine, 1e) is the most potent and selective H-3 antagonist from this series of 4(5)-(omega-aminoalkyl)-1H-imidazoles 1, with a pA(2) value of 8.4 (on guinea pig jejunum). A specific antagonistic binding site for this compound is proposed.