N,N'-bis(6-aminohexyl)cystamine | 68536-04-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: N,N'-bis(6-aminohexyl)cystamine
• 英文别名: N'-[2-[2-(6-aminohexylamino)ethyldisulfanyl]ethyl]hexane-1,6-diamine
• CAS: 68536-04-9
• 化学式: C₁₆H₃₈N₄S₂
• 分子量: 350.637
• InChiKey: HWCJBHIDZTXVIO-UHFFFAOYSA-N

物化性质

• 沸点：
  495.9±45.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(6-aminohexyl)cystamine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 6.0h， 生成 N,N'-bis<6-<(2-hydroxybenzyl)amino>hex-1-yl>cystamine
  参考文献：
  名称：

  Structure-activity relationships among di- and tetramine disulfides related to benextramine

  摘要：

  The synthesis and irreversible alpha-blocking activity in the rat vas deferens of a series of tetra- and diamine disulfides 2-38, structural analogues of benextramine (BHC), are described. All compounds containing a central cystamine moiety displayed an irreversible alpha-adrenergic blockade at concentrations ranging from 10(-4) to 6 X 10(-6)M. Potency was increased in cystamines N,N'-disubstituted with 6-aminohexyl groups, especially when the outer nitrogen atoms bear arylalkyl substituents or are enclosed in a ring. However, N,N,N',N'-tetrasubstituted cystamines were poor blockers. Structural specificity in the outer portion of the tetramine disulfide is low, since many types of substituents gave rise to potent alpha-blockers. Even replacement of the outer amines with nonbasic ethers or amides was observed to maintain irreversible alpha-blockade.

  DOI：

  10.1021/jm00390a011
• 作为产物：
  描述：

  N,N'-bis(6-aminohexanoyl)cystamine 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N,N'-bis(6-aminohexyl)cystamine
  参考文献：
  名称：

  Benextramine-neuropeptide Y受体的相互作用：苄基部分对[3H] neuropeptide Y置换活性的贡献。

  摘要：

  使用溶液相肽合成方法合成了N，N'-双[6-[（[2-甲氧基苄基）氨基]己-1-基]胱胺的类似物（benextramine，BXT，2），并分析了取代特异性结合的活性1 nM N- [丙酰-3H]神经肽Y（[3H] NPY）来自大鼠脑中对苯乙胺敏感的神经肽Y（NPY）结合位点。我们对这些类似物的新合成方法开始于，将胱胺与叔丁氧羰基（t-Boc）保护的6-氨基己酸的N-羟基琥珀酰亚胺酯酰化，然后用在二恶烷中的4 N HCl脱保护t-Boc基团。用适当取代的苯甲酸的N-羟基琥珀酰亚胺酯将该对称的二胺酰化，然后在回流的THF中用乙硼烷还原所得的四酰胺，得到目标化合物。缺乏苄基的BXT类似物（即化合物11）在浓度高达1.4 x 10（-3）M时没有[3H] NPY置换活性。邻位，间位和对位的活性范围是9倍在对苯达拉明敏感的NPY大鼠大脑结合位点的甲氧基，氯代和羟基苯达拉明类似物的区域异构体与在α-

  DOI：

  10.1021/jm00054a012

文献信息

• Analogues of Prazosin That Bear a Benextramine-Related Polyamine Backbone Exhibit Different Antagonism toward α₁-Adrenoreceptor Subtypes
  作者：Maria L. Bolognesi、Gabriella Marucci、Piero Angeli、Michela Buccioni、Anna Minarini、Michela Rosini、Vincenzo Tumiatti、Carlo Melchiorre

  DOI：10.1021/jm000995w

  日期：2001.2.1

  Hybrid tetraaamine disulfides 4-9 were synthesized by combining the structural features of prazosin (1), a competitive alpha (1)-adrenoreceptor antagonist, and benextramine (2), an irreversible alpha (1)/alpha (2)-adrenoreceptor antagonist, and their biological profiles at alpha (1)-adrenoreceptor subtypes were assessed by functional experiments in isolated rat vas deferens (alpha (1A)), spleen (alpha (1B)), and aorta (alpha (1D)). To verify the role of the disulfide moiety on the interaction with alpha (1)-adrenorcceptor subtypes, carbon analogues 10-15 were included in this study. All quinazolines lacking the disulfide bridge behaved, like 1, as competitive antagonists, whereas all polyamine disulfides displayed a nonhomogeneous mechanism of inhibition at the three subtypes since they were, like 2, noncompetitive antagonists at the alpha (1A) and alpha (1B) subtypes while being, unlike 2, competitive antagonists at the alpha (1D). In particular, the blocking effects were characterized by a decrease of the maximal response to noradrenaline that was affected only slightly by washings. Probably the alpha (1A) and alpha (1B) subtypes bear in the binding pocket a suitable thiol function that would suffer an interchange reaction with the disulfide moiety of the antagonist and which is missing, or not accessible, in the alpha (1D) subtype. Polyamines 8, 9, and 14, among others, emerged as promising tools for the characterization of al-adrenoreceptors, owing to their receptor subtype selectivity. Finally, the effect of nonbasic substituents on the phenyl ring of prazosin analogues 16-28 on potency and selectivity for the different subtypes can hardly be rationalized.
• Melchiorre; Gulini; Giardina, European Journal of Medicinal Chemistry, 1984, vol. 19, # 1, p. 37 - 42
  作者：Melchiorre、Gulini、Giardina、et al.

  DOI：——

  日期：——
• Brasili; Giannella; Melchiorre, European Journal of Medicinal Chemistry, 1981, vol. 16, # 2, p. 115 - 118
  作者：Brasili、Giannella、Melchiorre、et al.

  DOI：——

  日期：——
• Molecular properties of the adrenergic .alpha. receptor. 2. Optimum covalent inhibition by two different prototypes of polyamine disulfides
  作者：Carlo Melchiorre、Man Sen Yong、Bruno G. Benfey、Bernard Belleau

  DOI：10.1021/jm00209a007

  日期：1978.11
• ANGELI, P.;BRASILI, L.;BRANCIA, E.;GIARDINA, D.;QUAGLIA, W.;MELCHIORRE, C+, J. MED. CHEM., 1985, 28, N 11, 1643-1647
  作者：ANGELI, P.、BRASILI, L.、BRANCIA, E.、GIARDINA, D.、QUAGLIA, W.、MELCHIORRE, C+

  DOI：——

  日期：——