N1-(3,4-dimethoxybenzyl)-N7-(1,2,3,4-tetrahydroacridin-9-yl)heptane-1,7-diamine | 1268720-60-0

• 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: N1-(3,4-dimethoxybenzyl)-N7-(1,2,3,4-tetrahydroacridin-9-yl)heptane-1,7-diamine
• 英文别名: N-[(3,4-dimethoxyphenyl)methyl]-N'-(1,2,3,4-tetrahydroacridin-9-yl)heptane-1,7-diamine
• CAS: 1268720-60-0
• 化学式: C₂₉H₃₉N₃O₂
• 分子量: 461.648
• InChiKey: DECRHYMHDWBJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(7-aminoheptyl)-1,2,3,4-tetrahydroacridin-9-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 N1-(3,4-dimethoxybenzyl)-N7-(1,2,3,4-tetrahydroacridin-9-yl)heptane-1,7-diamine
  参考文献：
  名称：

  设计，合成和评估新型他克林-多烷氧基苯杂化物作为胆碱酯酶和淀粉样β聚集的双重抑制剂

  摘要：

  一系列新的他克林-multialkoxybenzene杂种（的图9a - 9N）设计，合成和评价为胆碱酯酶（胆碱酯酶）和自诱导β的双重抑制剂-淀粉样蛋白（Aβ）聚集。所有合成的化合物均具有较高的乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）抑制活性，IC 50值在纳摩尔范围内，比单独使用他克林要好得多。Lineweaver-Burk图和分子建模研究表明，这些杂种同时针对AChE的催化活性位点（CAS）和外围阴离子位点（PAS）。此外，化合物9a – 9f具有亚甲二氧基苯部分的化合物显示出比参考化合物姜黄素更高的自我诱导的Aβ聚集抑制活性。这些化合物可以被选作多效药物，以进一步研究治疗AD。

  DOI：

  10.1016/j.bmc.2010.12.022

文献信息

• Synthesis and evaluation of heterobivalent tacrine derivatives as potential multi-functional anti-Alzheimer agents
  作者：Wen Luo、Yan-Ping Li、Yan He、Shi-Liang Huang、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2011.03.058

  日期：2011.6

  A new series of heterobivalent tacrine derivatives were designed, synthesized and evaluated as potential multi-functional anti-Alzheimer agents for their inhibitory activity on cholinesterases, antioxidant activity and self-induced beta-amyloid (A beta) aggregation. All these synthesized compounds had potent inhibition activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) at nanomolar range. A Lineweaver-Burk plot and molecular modeling study showed that these compounds targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. The compounds containing hydroxyl group showed potent peroxyl radical absorbance activity. In addition, compound 5j exhibited higher self-induced A beta aggregation inhibitory activity than curcumin, which could become a multifunctional agent for further development for the treatment of AD. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as dual inhibitors for cholinesterases and amyloid beta aggregation
  作者：Wen Luo、Yan-Ping Li、Yan He、Shi-Liang Huang、Jia-Heng Tan、Tian-Miao Ou、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.bmc.2010.12.022

  日期：2011.1

  evaluated as dual inhibitors of cholinesterases (ChEs) and self-induced β-amyloid (Aβ) aggregation. All the synthesized compounds had high acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitory activity with IC50 values at the nanomolar range, which were much better than tacrine alone. A Lineweaver–Burk plot and molecular modeling study showed that these hybrids targeted both the catalytic

  一系列新的他克林-multialkoxybenzene杂种（的图9a - 9N）设计，合成和评价为胆碱酯酶（胆碱酯酶）和自诱导β的双重抑制剂-淀粉样蛋白（Aβ）聚集。所有合成的化合物均具有较高的乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）抑制活性，IC 50值在纳摩尔范围内，比单独使用他克林要好得多。Lineweaver-Burk图和分子建模研究表明，这些杂种同时针对AChE的催化活性位点（CAS）和外围阴离子位点（PAS）。此外，化合物9a – 9f具有亚甲二氧基苯部分的化合物显示出比参考化合物姜黄素更高的自我诱导的Aβ聚集抑制活性。这些化合物可以被选作多效药物，以进一步研究治疗AD。