1,8-octanediguanidinium sulphate | 39756-29-1

• 分子结构分类: 有机化合物 - 有机盐 - 有机硫酸盐
• 英文名称: 1,8-octanediguanidinium sulphate
• 英文别名: octane-1,8-diguanidium sulfate；2-[8-(Diaminomethylideneamino)octyl]guanidine;sulfuric acid；2-[8-(diaminomethylideneamino)octyl]guanidine;sulfuric acid
• CAS: 39756-29-1
• 化学式: C₁₀H₂₄N₆*H₂O₄S
• 分子量: 326.42
• InChiKey: NROMIIREHKSQRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  221
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,8-辛二胺 、 S-甲基异硫脲硫酸盐 以 水 为溶剂， 反应 5.0h， 以60%的产率得到1,8-octanediguanidinium sulphate
  参考文献：
  名称：

  阻断神经元烟碱乙酰胆碱受体的烷二胍化合物的合成与药理作用。

  摘要：

  以来自漏斗网蜘蛛毒液的多胺毒素级分FTX和胍乙啶的胍基部分为模型，获得了一系列的氮杂烷-1，ω-双胍盐。其中一些阻滞了通过乙酰胆碱（nAChR）神经元烟碱受体的离子通量。阻断作用发生在亚微摩尔浓度，表明与nAChR具有高度选择性的相互作用。实际上，nAChR离子通道上的活性化合物无法识别牛肾上腺嗜铬细胞的电压依赖性Na +或Ca2 +通道。因此，这些化合物可能是阐明nAChR受体在中枢神经系统和外周神经系统中的功能的有用工具。

  DOI：

  10.1016/0968-0896(96)00108-3

文献信息

• Synthesis and pharmacology of Alkanediguanidinium compounds that block the neuronal nicotinic acetylcholine receptor
  作者：Mercedes Villarroya、Luis Gandía、Manuela G. López、Antonio G. García、Sénida Cueto、José-Luis García-Navio、Julio Alvarez-Builla

  DOI：10.1016/0968-0896(96)00108-3

  日期：1996.8

  Taking as models the polyamine toxin fraction FTX from the funnel-web spider venom, and the guanidinium moiety of guanethidine, a series of azaalkane-1, omega-diguanidinium salts were obtained. Some of them blocked ion fluxes through the neuronal nicotinic receptors for acetylcholine (nAChR). The blockade was exerted at submicromolar concentrations, suggesting a highly selective interaction with the

  以来自漏斗网蜘蛛毒液的多胺毒素级分FTX和胍乙啶的胍基部分为模型，获得了一系列的氮杂烷-1，ω-双胍盐。其中一些阻滞了通过乙酰胆碱（nAChR）神经元烟碱受体的离子通量。阻断作用发生在亚微摩尔浓度，表明与nAChR具有高度选择性的相互作用。实际上，nAChR离子通道上的活性化合物无法识别牛肾上腺嗜铬细胞的电压依赖性Na +或Ca2 +通道。因此，这些化合物可能是阐明nAChR受体在中枢神经系统和外周神经系统中的功能的有用工具。
• I 2 -Imidazoline Binding Site Affinity of a Structurally Different Type of Ligands
  作者：Christophe Dardonville、Isabel Rozas、Luis F Callado、J.Javier Meana

  DOI：10.1016/s0968-0896(01)00420-5

  日期：2002.5

  Two families of compounds with affinity towards the I-2 imidazoline binding sites are reported. The first is a family of compounds structurally related to agmatine with two guanidine or 2-aminoimidazoline groups at each end of an aliphatic chain of six, eight, nine or 12 methylene groups. Second, and following the model of clonidine, we propose another family of compounds also with two guanidine or 2-aminoimidazoline groups at each end of a chain consisting of two phenyl rings connected by groups such as CH2, CO, NH and SO2, The affinity of the compounds towards the I-2 imidazoline binding sites was then evaluated in human brain tissues. In order to determine their pharmacological selectivity versus alpha(2)-adrenoceptors. the affinity for these receptors was also evaluated for the compounds with the highest affinities at I-2 imidazoline binding sites. The results obtained show that many of the compounds exhibit a considerable affinity towards the I-2 imidazoline binding sites. The aliphatic derivatives, in particular, present a very interesting selectivity for the I-2 imidazoline binding sites versus the alpha(2) adrenoceptors. To better understand these findings, mono-guanidinium analogues of the aliphatic derivatives were synthesised and tested showing poor affinity for I-2 imidazoline binding sites. The importance of these results lies in the novelty of the chemical structures studied (dicationic aliphatic compounds particularly) because they are significantly different to those of the I-2 imidazoline binding site ligands reported to date. (C) 2002 Published by Elsevier Science Ltd.