Alpha, beta-unsaturated cyclohexanone derivatives and application thereof

A technology of cyclohexanone and derivatives, which is applied in the field of α,β-unsaturated cyclohexanone derivatives, can solve the problems of consuming large resources and money, and achieve good application prospects

Inactive Publication Date: 2016-11-09
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Every health system in the world is severely impacted by dementia and consumes a lot of resources and money to care for people with dementia

Method used

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  • Alpha, beta-unsaturated cyclohexanone derivatives and application thereof
  • Alpha, beta-unsaturated cyclohexanone derivatives and application thereof
  • Alpha, beta-unsaturated cyclohexanone derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of compound 2,6-bis(2-chloro-3-methoxybenzylidene)cyclohexanone (3a):

[0058] Cyclohexanone (10mmol, 1eq) and 2-chloro-3-methoxybenzaldehyde (20mmol, 2eq) were added to a round bottom flask containing 25mL of ethanol, and the temperature was maintained 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 85%.

[0059] Mp: 112-114°C; 1 H NMR (500MHz, CDCl 3 )δ: 7.89(s, 2H), 6.90(t, J=8.5Hz, 2H), 6.89(d, J=8.5Hz, 2H), 6.50(d, J=8.5Hz, 2H), 3.72(s, 6H), 2.35(t, J=8.0Hz, 4H), 1.81(m, 2H); 13 C NMR (500MHz, CDCl 3 )δ: 185.2, 152.4, 146.7, 145.2, 144.1, 135.6, 131.2, 107.2, 98.2, 56.7, 28.2, 27.1; HRMS...

Embodiment 2

[0061] 2,6-bis(2-chloro-3,4-dimethoxybenzylidene)cyclohexanone (3b)

[0062] The starting materials are cyclohexanone (10mmol, 1eq) and 2-chloro-3,4-dimethoxybenzaldehyde (20mmol, 2eq). Others are the same as in Example 1, and the yield is 82%.

[0063] Mp:117-118℃; 1 H NMR (500MHz, CDCl 3 )δ: 7.79(s, 2H), 6.92(d, J=8Hz, 2H), 6.54(d, J=8Hz, 2H), 3.70(s, 12H), 2.36(t, J=8.0Hz, 4H) ,1.86(m,2H); 13 C NMR (500MHz, CDCl 3 )δ: 186.2, 150.8, 146.4, 144.5, 142.6, 136.2, 130.1, 108.7, 98.3, 56.6, 56.1, 28.7, 26.9; HRMS (ESI) m / z: 464.35 [M+H] + ,Microanalysis calculated for C 24 h 24 Cl 2 o 5 (463.35), C:62.21%, H:5.22%. Found C:62.25%, H:5.25%.

Embodiment 3

[0065] 2,6-bis(2-bromo-3,4,5-trimethoxybenzylidene)cyclohexanone (3c)

[0066] The starting materials are cyclohexanone (10mmol, 1eq) and 2-bromo-3,4,5-trimethoxybenzaldehyde (20mmol, 2eq). Others are the same as in Example 1, and the yield is 74%.

[0067] Mp: 102-103°C; 1 H NMR (500MHz, CDCl 3 )δ: 7.82(s, 2H), 6.89(s, 2H), 3.75(s, 18H), 2.32(t, J=8.0Hz, 4H), 1.82(m, 2H); 13 C NMR (500MHz, CDCl 3 )δ: 185.4, 151.2, 146.5, 144.2, 144.9, 135.9, 130.5, 108.4, 98.6, 56.5, 56.1, 55.5, 28.5, 27.3; HRMS (ESI) m / z: 613.32 [M+H] + ,Microanalysis calculated for C 26 h 28 Br 2 o 7 (612.30),C:51.00%,H:4.61%.Found C:51.22%,H:4.59%.

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Abstract

The invention discloses an alpha, beta-unsaturated cyclohexanone derivatives and application thereof as medicaments for preventing, treating or dignozing Alzheimer's disease. The alpha, beta-unsaturated cyclohexanone derivatives comprise 2,6-bis(2-chloro-3- methoxybenzylidene)cyclohexnone, 2,6-bis(2-chloro-3,4-dimethoxybenzylidene)cyclohexnone, 2,6-bis(2-bromo-3,4,5-trimethoxybenzylidene)cyclohexnone, 2,6-bis(2-chloro-3-methoxybenzylidene)-4-methylcyclohexnone, 2,6-bis(2-chloro-3,4-dimethoxybenzylidene)-4-methylcyclohexnone and the like. Through bioactivity determination, the alpha, beta-unsaturated cyclohexanone derivatives are proved to possess pharmacological activity related to resistance to Alzheimer's disease, is applicable as medicaments to prevent, treat and diagnose Alzheimer's disease, and possesses relatively good potential application prospect.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, and specifically relates to an α, β-unsaturated cyclohexanone derivative and an application thereof. Background technique [0002] Dementia is one of the most disabling conditions in the elderly. Every health system in the world is severely impacted by dementia, requiring enormous resources and money to care for people with dementia. Alzheimer's disease is the most common disease that causes dementia, and its main symptom is persistent loss of memory and other neurological functions. Alzheimer's disease can completely incapacitate patients for up to 10 years, resulting in a huge financial and emotional burden for patients and their families. [0003] Based on the "cholinergic hypothesis", damage to choline function, especially to the hippocampus and neocortex in the brain that process emotional responses, behavior, memory and learning, is the main cause of Alzheimer's disease. The most obviou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/753C07D213/68C07D309/38A61K31/122A61K31/45A61K31/351A61P25/28
CPCC07C49/753C07D213/68C07D309/38
Inventor 秦华利郝建宏冷静查高峰
Owner WUHAN UNIV OF TECH
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