5-(4-aminobutyl)-2-thiopheneoctanamine | 207909-01-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(4-aminobutyl)-2-thiopheneoctanamine
• 英文别名: N4T8N；8-[5-(4-Aminobutyl)thiophen-2-yl]octan-1-amine
• CAS: 207909-01-1
• 化学式: C₁₆H₃₀N₂S
• 分子量: 282.494
• InChiKey: PSYVYGLWUVDAGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-aminobutyl)-2-thiopheneoctanamine 在 盐酸 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 0.5h， 生成 N-{8-[5-(4-guanidinobutyl)thien-2-yl]octyl}guanidine dihydrochloride
  参考文献：
  名称：

  New polyamine-sensitive inhibitors of the NMDA receptor: Syntheses and pharmacological evaluation

  摘要：

  Derivatives of 5-(4-an-nobutyl)-2-thiophene-octylamine, a potent polyamine-sensitive inhibitor of the NMDA receptor, were synthesized and evaluated as inhibitors of [H-3]MK-801 binding to rat brain membranes. Alkylations of the terminal amino groups reduced inhibitory potency; only incorporation of the amino group of the short 4-aminobutyl arm into a piperidine ring was tolerated. Substitution of the thiophene nucleus with methyl or ethyl, and its replacement by a benzene nucleus, was of minor influence. The corresponding diguanidines exhibited high potency independent of chain length, whereas their sensitivity to spermine was sharply dependent on chain length. Insertion of an amide bond into the long octylamine arm increased sensitivity to spermine and to Tris buffer. Our results indicate that spermine sensitivity of [H-3]MK-801 binding inhibition is responsive to subtle changes in inhibitor structure and represents a promising target for pharmaceutical research. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.017
• 作为产物：
  描述：

  Methyl 8-[5-(4-methoxy-4-oxobutanoyl)thiophen-2-yl]octanoate 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 草酰氯 、 氨 、 一水合肼 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 生成 5-(4-aminobutyl)-2-thiopheneoctanamine
  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