N,N'-bis<6-<(2-hydroxybenzyl)amino>hex-1-yl>cystamine | 97125-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis<6-<(2-hydroxybenzyl)amino>hex-1-yl>cystamine
• 英文别名: N,N'-bis[6-[(2-hydroxybenzyl)amino]hex-1-yl]cystamine；Phenol, 2,2'-(12,13-dithia-2,9,16,23-tetraazatetracosane-1,24-diyl)bis-；2-[[6-[2-[2-[6-[(2-hydroxyphenyl)methylamino]hexylamino]ethyldisulfanyl]ethylamino]hexylamino]methyl]phenol
• CAS: 97125-00-3
• 化学式: C₃₀H₅₀N₄O₂S₂
• 分子量: 562.885
• InChiKey: KCCRQRMNWRIRHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N,N'-bis<6-<(2-hydroxybenzyl)amino>hex-1-yl>cystamine 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以78%的产率得到6-(2,4-dihydro-1,3-benzoxazin-3-yl)-N-[2-[2-[6-(2,4-dihydro-1,3-benzoxazin-3-yl)hexylamino]ethyldisulfanyl]ethyl]hexan-1-amine
  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：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 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

文献信息

• Benextramine-neuropeptide Y receptor interactions: contribution of the benzylic moieties to [3H]neuropeptide Y displacement activity
  作者：Michael B. Doughty、Chandra S. Chaurasia、Ke Li

  DOI：10.1021/jm00054a012

  日期：1993.1

  6-aminohexanoic acid, followed by deprotection of the t-Boc groups with 4 N HCl in dioxane. Acylation of this symmetric diamine with N-hydroxysuccinimide esters of appropriately substituted benzoic acids, followed by reduction of the resultant tetraamides with diborane in refluxing THF, afforded the target compounds. The BXT analog lacking the benzylic group (i.e., compound 11) had no [3H]NPY displacement activity

  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-
• ALVAREZ, M.;GRANADOS, R.;MAULEON, D.;ROSELL, G.;SALAS, M.;SALLES, J.;VALL+, J. MED. CHEM., 30,(1987) N 7, 1186-1193
  作者：ALVAREZ, M.、GRANADOS, R.、MAULEON, D.、ROSELL, G.、SALAS, M.、SALLES, J.、VALL+

  DOI：——

  日期：——
• Structure-activity relationships among di- and tetramine disulfides related to benextramine
  作者：M. Alvarez、R. Granados、D. Mauleon、G. Rosell、M. Salas、J. Salles、N. Valls

  DOI：10.1021/jm00390a011

  日期：1987.7

  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.