8-[5-(8-Amino-8-oxooctyl)thiophen-2-yl]octanamide | 207908-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 8-[5-(8-Amino-8-oxooctyl)thiophen-2-yl]octanamide
• CAS: 207908-83-6
• 化学式: C₂₀H₃₄N₂O₂S
• 分子量: 366.568
• InChiKey: MNFUKMAZYAFUOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-[5-(8-Amino-8-oxooctyl)thiophen-2-yl]octanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 8-[5-(8-Aminooctyl)thiophen-2-yl]octan-1-amine
  参考文献：
  名称：

  Inverse agonists at the polyamine-sensitive modulatory site of the NMDA receptor: 50-fold increase in potency by insertion of an aromatic ring into an alkanediamine chain

  摘要：

  Polyamines like spermine and spermidine increase the opening frequency of the NMDA receptor associated ion channel and, as a consequence, specific binding of non-saturating concentrations of the channel radioligand [H-3]MK-801. Compounds exhibiting the contrary effect have been described as polyamine inverse agonists, with 1,12-dodecanediamine (N-12-N) being one of the most specific ones (IC50 16.5 mu M). Here we describe the synthesis of a series of long-chain alkanediamines, with a thiophene nucleus inserted at various positions, and report the discovery of 5-(4-aminobutyl)-2-thiopheneoctanamine (N-4-T-8-N), which inhibited specific binding of [H-3]MK-801 by 50 % at 0.33 mu M. In the presence of 100 mu M of spermine, 4.0 mu M N-4-T-8-N was necessary to achieve the same degree of inhibition. N-4-T-8-N is the most potent polyamine inverse agonist presently known and should be a useful tool to elucidate the physiological significance of the polyamine regulatory site of the NMDA receptor complex. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80070-1
• 作为产物：
  描述：

  8-[5-(7-Carboxyheptyl)thiophen-2-yl]octanoic acid 在 吡啶 、 草酰氯 、 氨 作用下， 生成 8-[5-(8-Amino-8-oxooctyl)thiophen-2-yl]octanamide
  参考文献：
  名称：

  Inverse agonists at the polyamine-sensitive modulatory site of the NMDA receptor: 50-fold increase in potency by insertion of an aromatic ring into an alkanediamine chain

  摘要：

  Polyamines like spermine and spermidine increase the opening frequency of the NMDA receptor associated ion channel and, as a consequence, specific binding of non-saturating concentrations of the channel radioligand [H-3]MK-801. Compounds exhibiting the contrary effect have been described as polyamine inverse agonists, with 1,12-dodecanediamine (N-12-N) being one of the most specific ones (IC50 16.5 mu M). Here we describe the synthesis of a series of long-chain alkanediamines, with a thiophene nucleus inserted at various positions, and report the discovery of 5-(4-aminobutyl)-2-thiopheneoctanamine (N-4-T-8-N), which inhibited specific binding of [H-3]MK-801 by 50 % at 0.33 mu M. In the presence of 100 mu M of spermine, 4.0 mu M N-4-T-8-N was necessary to achieve the same degree of inhibition. N-4-T-8-N is the most potent polyamine inverse agonist presently known and should be a useful tool to elucidate the physiological significance of the polyamine regulatory site of the NMDA receptor complex. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80070-1