10-(3-pyrrolidinopropylamino)-7H-dibenzo[de,h]quinolin-7-one | 1365641-16-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 异卟啉
• 英文名称: 10-(3-pyrrolidinopropylamino)-7H-dibenzo[de,h]quinolin-7-one
• 英文别名: 4-(3-Pyrrolidin-1-ylpropylamino)-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-8-one
• CAS: 1365641-16-2
• 化学式: C₂₃H₂₃N₃O
• 分子量: 357.455
• InChiKey: AROJOJHHBFSORT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(3-氨基丙基)吡咯烷 、 10-chloro-1-aza-benzanthrone 在 sodium iodide 作用下， 以 戊醇 为溶剂， 以36%的产率得到10-(3-pyrrolidinopropylamino)-7H-dibenzo[de,h]quinolin-7-one
  参考文献：
  名称：

  Novel oxoisoaporphine-based inhibitors of acetyl- and butyrylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation

  摘要：

  A series of novel oxoisoaporphine-based inhibitors (10-aminoalkylamino-1-azabenzanthrone ArNH(CH2)(n)(NRR2)-R-1) of acetylcholinesterase (AChE) has been designed, synthesized, and tested for their ability to inhibit AChE, butyrylcholinesterase (BChE) and AChE-induced beta-amyloid (A beta) aggregation. The synthetic compounds exhibited high AChE inhibitory activity with IC50 values in the submicromolar range in most cases. Non-competitive binding mode was found for these derivatives by the graphical analysis of steady-state inhibition data. Moreover, all compounds exhibit significant inhibitory activity on AChE-induced A beta aggregation with inhibitory potency from 54.5% to 93.5%. Finally, six out of twelve synthetic compounds were predicted to be able to cross the blood-brain barrier (BBB) to reach their targets in the central nervous system (CNS) according to a parallel artificial membrane permeation assay for BBB. The result encourages us to study this class of compounds thoroughly and systematically. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.090

文献信息

• Novel oxoisoaporphine-based inhibitors of acetyl- and butyrylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation
  作者：Huang Tang、Hai-Tao Zhao、Shu-Ming Zhong、Zhi-Yu Wang、Zhen-Feng Chen、Hong Liang

  DOI：10.1016/j.bmcl.2012.01.090

  日期：2012.3

  A series of novel oxoisoaporphine-based inhibitors (10-aminoalkylamino-1-azabenzanthrone ArNH(CH2)(n)(NRR2)-R-1) of acetylcholinesterase (AChE) has been designed, synthesized, and tested for their ability to inhibit AChE, butyrylcholinesterase (BChE) and AChE-induced beta-amyloid (A beta) aggregation. The synthetic compounds exhibited high AChE inhibitory activity with IC50 values in the submicromolar range in most cases. Non-competitive binding mode was found for these derivatives by the graphical analysis of steady-state inhibition data. Moreover, all compounds exhibit significant inhibitory activity on AChE-induced A beta aggregation with inhibitory potency from 54.5% to 93.5%. Finally, six out of twelve synthetic compounds were predicted to be able to cross the blood-brain barrier (BBB) to reach their targets in the central nervous system (CNS) according to a parallel artificial membrane permeation assay for BBB. The result encourages us to study this class of compounds thoroughly and systematically. (C) 2012 Elsevier Ltd. All rights reserved.