1-(4-acetylphenyl)-3-[4-(3-piperidin-1-ylpropoxy)benzene]sulfonylurea | 1375454-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-acetylphenyl)-3-[4-(3-piperidin-1-ylpropoxy)benzene]sulfonylurea
• 英文别名: 1-(4-Acetylphenyl)-3-[4-(3-piperidin-1-ylpropoxy)phenyl]sulfonylurea
• CAS: 1375454-19-5
• 化学式: C₂₃H₂₉N₃O₅S
• 分子量: 459.566
• InChiKey: QCLNKICPVIDCPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-苯氧基溴丙烷 在 氯磺酸 、 氨 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 27.92h， 生成 1-(4-acetylphenyl)-3-[4-(3-piperidin-1-ylpropoxy)benzene]sulfonylurea
  参考文献：
  名称：

  Novel sulfonylurea derivatives as H3 receptor antagonists. Preliminary SAR studies

  摘要：

  The combination of antagonism at histamine H-3 receptor and the stimulation of insulin secretion have been proposed as an approach to new dual therapeutic agents for the treatment of type 2 diabetes mellitus associated with obesity. We have designed and synthesized a new series of non-imidazole derivatives, based on a basic amine ring connected through an alkyl spacer of variable length to a phenoxysulfonylurea moiety. These compounds were initially evaluated for histamine H-3 receptor binding affinities, suggesting that a propoxy chain linker between the amine and the core ring could be essential for optimal binding affinity. Compound 56, 1-(naphthalen-1-yl)-3-[(p-(3-pyrrolidin-1-ylpropoxy) benzene)]sulfonylurea exhibited the best H-3 antagonism affinity. However, since all these derivatives failed to block K-ATP channels, the link of these two related moieties should not be considered a good pharmacophore for obtaining new dual H-3 antagonists with insulinotropic activity, suggesting the necessity to propose a new chemical hybrid prototype. (C)2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.049