N-Adamantan-1-yl-N'-{4-[4-(adamantan-1-ylamino)-butylamino]-butyl}-butane-1,4-diamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-Adamantan-1-yl-N'-{4-[4-(adamantan-1-ylamino)-butylamino]-butyl}-butane-1,4-diamine
• 英文别名: N,N'-bis[4-(1-adamantylamino)butyl]butane-1,4-diamine
• 化学式: C₃₂H₅₈N₄
• 分子量: 498.839
• InChiKey: FEXNVNVPGQVKBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N¹,N⁵,N¹⁰,N¹⁴-tetrakis(p-toluenesulfonyl)-N¹,N¹⁴-bis(1-adamantyl)homospermine 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-Adamantan-1-yl-N'-{4-[4-(adamantan-1-ylamino)-butylamino]-butyl}-butane-1,4-diamine
  参考文献：
  名称：

  Impact of Polyamine Analogs on the NMDA Receptor

  摘要：

  Several N,N'-terminal dialkylated homologs of the tetraamine spermine exhibit a pronounced biphasic activity at the N-methyl-D-aspartate (NMDA) receptor-channel complex in rat cerebral cortex membranes in the presence of 100 mu M L-glutamate and 100 mu M glycine. At low micromolar polyamine concentrations, these analogs enhance binding of [H-3]-(+)-5-methyl-10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine ([H-3]MK-801) similar to spermine (SPM). At higher concentrations (e.g., greater than or equal to 10 mu M), the analogs are antagonists of [H-3]MK-801 binding. The most potent analog, N-1,N-14-bis(1-adamantyl)homospermine, is almost totally devoid of agonist activity and is a potent antagonist at concentrations greater than or equal to 5 mu M. Three structural features of the tetraamines studied appear to correlate with potency of inhibition: (1) N-terminally alkylated polyamines > terminal primary amines (e.g., SPM); (2) length of the polyamine backbone, e.g., DMHSPM > DMNSPM; and (3) size of the terminal alkyl groups, i.e., adamantyl > tert-butyl > ethyl > methyl. These findings emphasize the potential. of the tetraamine backbone as a pharmacophore to modulate NMDA receptor-channel function.

  DOI：

  10.1021/jm00003a004