1-苄基-4-((5,6-二甲氧基-2,3-二氢-1H-茚-2-基)甲基)哌啶盐酸盐 | 1034439-57-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-苄基-4-((5,6-二甲氧基-2,3-二氢-1H-茚-2-基)甲基)哌啶盐酸盐
• 中文别名: 1-苄基-4-((5,6-二甲氧基-2,3-二氢-1H-茚-2
• 英文名称: 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindane hydrochloride
• 英文别名: Deoxy Donepezil Hydrochloride；1-benzyl-4-[(5,6-dimethoxy-2,3-dihydro-1H-inden-2-yl)methyl]piperidine;hydrochloride
• CAS: 1034439-57-0
• 化学式: C₂₄H₃₁NO₂*ClH
• 分子量: 401.977
• InChiKey: PJOSEOQZAOZSMV-UHFFFAOYSA-N

物化性质

• 熔点：
  202-205°C
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微）、水（轻微、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  多奈哌齐杂质D 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以161 mg的产率得到1-苄基-4-((5,6-二甲氧基-2,3-二氢-1H-茚-2-基)甲基)哌啶盐酸盐
  参考文献：
  名称：

  Novel Donepezil-Based Inhibitors of Acetyl- and Butyrylcholinesterase and Acetylcholinesterase-Induced β-Amyloid Aggregation

  摘要：

  A novel series of donepezil-tacrine hybrids designed to simultaneously interact with the active, peripheral and midgorge binding sites of acetylcholinesterase (AChE) have been synthesized and tested for their ability to inhibit AChE, butyrylcholinesterase (BChE), and AChE-induced A beta aggregation. These compounds consist of a unit of tacrine or 6-chlorotacrine, which occupies the same position as tacrine at the AChE active site, and the 5,6-dimethoxy-2-[(4-piperidinyl)methyl]-1-indanone moiety of donepezil (or the indane derivative thereof), whose position along the enzyme gorge and the peripheral site can be modulated by a suitable tether that connects tacrine and donepezil fragments. All of the new compounds are highly potent inhibitors of bovine and human AChE and BChE, exhibiting IC50 values in the subnanomolar or low nanomolar range in most cases. Moreover, six out of the eight hybrids of the series, particularly those bearing an indane moiety, exhibit a significant A beta antiaggregating activity, which makes them promising anti-Alzheimer drug candidates.

  DOI：

  10.1021/jm8001313

文献信息

• Fractal analysis of catalyst surface morphologies on hydrogenation in process of 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride synthesis
  作者：Želimir Jelčić、Zrinka Mastelić Samardžić、Stanka Zrnčević

  DOI：10.1016/j.apcata.2013.02.011

  日期：2013.4

  Catalytic hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride (1) to 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride (2) was investigated in batch-slurry reactor. The 5% Pt/C catalysts were chosen for optimizing the catalytic activity. The catalyst activity has been changed by using the differently morphologically structured fractal catalysts. The kinetic terms of hydrogenation for (1) change with the fractal dimensions of the 5% Pt/C catalyst. The most active and selective (with the highest reaction rate for production of (2), and with the least impurities level) is the catalyst K3, and the worst the catalyst K4. This most active and selective catalyst has an intermediate fractal surface dimension, D-F,D-ads = 2.77, and the worst catalyst is represented by almost smooth surface with a high D-F,D-ads = 2.82. The interface D[BW] fractal indices (derived from the thresholded SEM images, at the magnifications in the range 600-2000x) are largest ones for the most suitable catalyst K3, and lowest for the catalyst K4. (C) 2013 Elsevier B.V. All rights reserved.