N,N'-Bis-(2-methyl-quinolin-4-yl)-octane-1,8-diamine; hydrochloride | 31892-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N'-Bis-(2-methyl-quinolin-4-yl)-octane-1,8-diamine; hydrochloride
• 英文别名: N,N'-bis(2-methylquinolin-4-yl)octane-1,8-diamine;hydrochloride
• CAS: 31892-51-0
• 化学式: C₂₈H₃₄N₄*2ClH
• 分子量: 499.527
• InChiKey: ZQCKKUIAQUBTNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,8-辛二胺 、 4-氯喹哪啶 以 戊醇 为溶剂， 以94%的产率得到N,N'-Bis-(2-methyl-quinolin-4-yl)-octane-1,8-diamine; hydrochloride
  参考文献：
  名称：

  Dual-site binding of bivalent 4-aminopyridine- and 4-aminoquinoline-based AChE inhibitors: contribution of the hydrophobic alkylene tether to monomer and dimer affinities

  摘要：

  Three series of 4-aminopyridine-and 4-aminoquinoline based symmetrical bivalent acetylcholinesterase (AChE) inhibitors were prepared and compared to previously synthesized dimers of 9-amino-1,2,3,4-tetrahydroacridine (tacrine). In each case significant, tether length-dependent increases in AChE inhibition potency and selectivity (up to 3000-fold) were observed relative to the corresponding monomer, indicating dual-site binding of these inhibitors to AChE. Assay of the corresponding alkylated monomers revealed that the alkylene tether played at least two complementary roles in the dimer series. In addition to reducing the entropy loss that occurs on binding both monomeric units of the dimer; the alkylene tether can also significantly improve potency through hydrophobic effects. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00178-9

文献信息

• Dual-site binding of bivalent 4-aminopyridine- and 4-aminoquinoline-based AChE inhibitors: contribution of the hydrophobic alkylene tether to monomer and dimer affinities
  作者：Yi Fan Han、Crystal P.-L Li、Ella Chow、Hong Wang、Yuan-Ping Pang、Paul R Carlier

  DOI：10.1016/s0968-0896(99)00178-9

  日期：1999.11

  Three series of 4-aminopyridine-and 4-aminoquinoline based symmetrical bivalent acetylcholinesterase (AChE) inhibitors were prepared and compared to previously synthesized dimers of 9-amino-1,2,3,4-tetrahydroacridine (tacrine). In each case significant, tether length-dependent increases in AChE inhibition potency and selectivity (up to 3000-fold) were observed relative to the corresponding monomer, indicating dual-site binding of these inhibitors to AChE. Assay of the corresponding alkylated monomers revealed that the alkylene tether played at least two complementary roles in the dimer series. In addition to reducing the entropy loss that occurs on binding both monomeric units of the dimer; the alkylene tether can also significantly improve potency through hydrophobic effects. (C) 1999 Elsevier Science Ltd. All rights reserved.