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Alpha, beta-unsaturated carbonyl tetralone derivative and application thereof

A carbonyl tetralone and tetralone technology are applied in the field of α, β-unsaturated carbonyl tetralone derivatives, which can solve the problems that have not been fully proven to have curative effects, and achieve the effect of good application prospects.

Inactive Publication Date: 2017-01-04
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional positioning therapy is just one of the methods that has not been fully proven effective, and requires a change in assumptions to allow researchers to design and develop new drugs

Method used

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  • Alpha, beta-unsaturated carbonyl tetralone derivative and application thereof
  • Alpha, beta-unsaturated carbonyl tetralone derivative and application thereof
  • Alpha, beta-unsaturated carbonyl tetralone derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Synthesis of compound 2-(2-bromo-3,4,5-trimethoxy-benzylidene)-4-methyl-tetralone (3f):

[0073] Add 4-methyl-tetralone (10mmol, 1eq) and 2-bromo-3,4,5-trimethoxybenzaldehyde (10mmol, 1eq) respectively in a round bottom flask containing 15mL of ethanol, and keep the temperature at 5°C. Afterwards, 40% sodium hydroxide ethanol solution was added. The mixture was stirred at 27°C for 1-24h. The appearance and color change of the precipitate indicated product formation. The reaction was monitored by TLC. When the reaction was complete, acidified ice was added to quench the reaction. Recrystallization or column chromatography was then performed to obtain a purified product with a yield of 69%.

[0074] Mp:90-91℃; 1 H NMR (500MHz, CDCl 3 )δ:7.69(s,H),7.27(d,J=7.5Hz,H),7.19(d,J=7.5Hz,H),7.07(t,J=7.5Hz,H),6.91(t, J=7.0Hz,H),6.47(s,H),3.56(s,9H),2.19(d,J=8.5Hz,2H),1.79(m,H);1.19(d,J=8.5Hz, 3H); 13C NMR (500MHz, CDCl3) δ: 184.5, 150.7, 149.1, 147.1, 146.8, 145.2, 137.3, ...

Embodiment 2

[0076] Synthesis of compound 2-(2-bromo-3,4,5-trimethoxy-benzylidene)-6-hydroxy-tetralone (3i):

[0077] The starting materials are 6-hydroxy-tetralone (10mmol, 1eq) and 2-bromo-3,4,5-trimethoxybenzaldehyde (10mmol, 1eq), the others are the same as in Example 4, and the yield is 72% .

[0078] Mp:94-95℃; 1 H NMR (500MHz, CDCl3 )δ:7.68(s,H),7.15(d,J=7.5Hz,H),7.02(t,J=7.0Hz,H),6.90(d,J=7.5Hz,H),6.42(s, H), 5.81(s, H), 3.52(s, 9H), 2.52(t, J=8.0Hz, 2H), 2.13(t, J=8.0Hz, 2H); 13 C NMR (500MHz, CDCl 3 )δ: 184.9, 159.6, 149.2, 147.2, 146.1, 140.2, 137.8, 134.4, 134.0, 130.5, 126.2, 122.4, 120.2, 105.5, 96.1, 56.8, 56.0, 55.8, 31.2, 27.8; HRMS (ESI) m / z :420.46[M+H] + ,Microanalysis calculated for C 20 h 19 BrO 5 (419.27),C:57.29%,H:4.57%.Found C:57.52%,H:4.65%.

Embodiment 3

[0080] Synthesis of compound 2-(2-bromo-3,4,5-trimethoxy-benzylidene)-7-methoxy-tetralone (3o):

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Abstract

The invention discloses an alpha, beta-unsaturated carbonyl tetralone derivative and application thereof. The alpha, beta-unsaturated carbonyl tetralone derivative has the following structural formula, wherein R1 represents methylene or -HC-CH3; R2 represents hydrogen atoms or methoxyl; R3 represents hydrogen atoms, chlorine atoms, methoxyl, bromine atoms, fluorine atoms or nitryl; R4 represents hydrogen atoms or methoxyl; R5 represents hydrogen atoms, hydroxyl or methoxyl; R'3 and R'4 respectively represent hydrogen atoms or methoxyl; R'6 represents chlorine atoms or bromine atoms. The synthetic compound has pharmacological activities associated with anti-Alzheimer's disease, and is suitable for serving as a drug that can prevent, treat and diagnose Alzheimer's disease, and has a good potential application prospect. (Please see the formula in the description).

Description

technical field [0001] The invention belongs to the technical field of pharmacy, and specifically relates to an α,β-unsaturated carbonyl tetralone derivative and an application thereof. Background technique [0002] Neurodegenerative diseases are complex diseases in which cell death is controlled by multiple pathways. Traditional localized therapy is just one of the methods that has not been fully proven to be effective, and requires a change in assumptions to allow researchers to design and develop new drugs. In our study, we investigated the efficacy of a series of α,β-unsaturated carbonyltetralone derivatives for the treatment of Alzheimer's disease. In addition, they also studied the cytotoxicity induced by β-amyloid. The following six compounds 3f, 3o, 3u, 3ae, 3af, and 3ag can protect neurons in PC12 cells from Aβ-induced cell death. Most of the in vitro cell experiments demonstrated that these compounds have potential inhibitory activities of monoamine oxidase b, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/755A61P25/28
CPCC07C49/755
Inventor 秦华利冷静尚振鹏查高峰方菀茵陈兴
Owner WUHAN UNIV OF TECH
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