3-(2-(1-methylpyrrolyl)-propionamino)-7,8-dehydrorutaecarpine | 1443150-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(2-(1-methylpyrrolyl)-propionamino)-7,8-dehydrorutaecarpine
• 英文别名: 3-(1-methylpyrrolidin-1-ium-1-yl)-N-(14-oxo-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,11,15(20),16,18-nonaen-17-yl)propanamide
• CAS: 1443150-42-2
• 化学式: C₂₆H₂₆N₅O₂
• 分子量: 440.525
• InChiKey: BDUDWPYTOJWNKS-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-Nitro-2-(trifluoromethyl)-1,2-dihydro-3,1-benzoxazin-4-one 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 24.5h， 生成 3-(2-(1-methylpyrrolyl)-propionamino)-7,8-dehydrorutaecarpine
  参考文献：
  名称：

  Synthesis and evaluation of 7,8-dehydrorutaecarpine derivatives as potential multifunctional agents for the treatment of Alzheimer's disease

  摘要：

  A series of 7,8-dehydrorutaecarpine derivatives were synthesized and characterized as potential multifunctional agents for treatment of Alzheimer's disease (AD). All of these synthetic compounds showed high acetylcholinesterase (AChE) inhibitory activity with IC50 values ranged from 0.60 to 196.7 nM, and good selectivity for AChE over butyrylcholinesterase (BuChE) (125- to 3225-fold). A Lineweaver-Burk plot and molecular modeling study indicated these compounds could bind to both catalytic active site and the peripheral anionic site of AChE. Besides, compounds showed higher activity of inhibiting AChE-induced amyloid-beta (A beta) aggregation than curcumin, higher anti-oxidative activity than Trolox, and could also be good metal chelators. Considering their low cytotoxicity, our results indicated that these derivatives provide good templates for developing new multifunctional agents for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.014

文献信息

• Synthesis and evaluation of 7,8-dehydrorutaecarpine derivatives as potential multifunctional agents for the treatment of Alzheimer's disease
  作者：Yan He、Pei-Fen Yao、Shuo-bin Chen、Zhi-hong Huang、Shi-Liang Huang、Jia-Heng Tan、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2013.02.014

  日期：2013.5

  A series of 7,8-dehydrorutaecarpine derivatives were synthesized and characterized as potential multifunctional agents for treatment of Alzheimer's disease (AD). All of these synthetic compounds showed high acetylcholinesterase (AChE) inhibitory activity with IC50 values ranged from 0.60 to 196.7 nM, and good selectivity for AChE over butyrylcholinesterase (BuChE) (125- to 3225-fold). A Lineweaver-Burk plot and molecular modeling study indicated these compounds could bind to both catalytic active site and the peripheral anionic site of AChE. Besides, compounds showed higher activity of inhibiting AChE-induced amyloid-beta (A beta) aggregation than curcumin, higher anti-oxidative activity than Trolox, and could also be good metal chelators. Considering their low cytotoxicity, our results indicated that these derivatives provide good templates for developing new multifunctional agents for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.