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9-aminoalkylamido-1-azabenznthrone derivative and its synthesis and application

A technology of aminoalkanoyl amido and benzanthrone, which is applied in the field of 9-aminoalkanoyl amido-1-azabenzoanthrone derivatives, can solve the problem of increased activity of butyrylcholinesterase, etc. Achieve the effects of reducing drug side effects, enhancing drug efficacy, and significantly inhibiting selectivity and specificity

Inactive Publication Date: 2007-08-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, the latest research found that the activity of butyrylcholinesterase in the synapses of patients with Alzheimer's disease did not increase significantly

Method used

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  • 9-aminoalkylamido-1-azabenznthrone derivative and its synthesis and application
  • 9-aminoalkylamido-1-azabenznthrone derivative and its synthesis and application
  • 9-aminoalkylamido-1-azabenznthrone derivative and its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of 9-(2-chloroacetamido)-1-azabenzoanthrone

[0023] 1.0g (4mm) of 9-amino-1-azabenzanthrone was refluxed in 10ml of chloroacetyl chloride for 3-4 hours, cooled, filtered, washed with ether, and the filtrate was recrystallized with DMF-ethanol to obtain yellow needles (compound 1) 1.1 g (about 85% yield). 1 H NMR (DMSO, 300MHz): δ4.35(s, 2H), 7.98(d, 1H, J=5.6Hz), 8.01-8.09(m, 2H), 8.41(d, 1H, J=8.2Hz), 8.51(d, 1H, J=2.2Hz), 8.54(d, 1H, J=7.2Hz), 8.73-8, 78(m, 2H), 10.76(s, 1H-CONH); ESI-MS m / z : 324[M+H] + .

[0024] The structural formula of the synthesized compound 1 is as follows:

[0025]

Embodiment 2

[0026] Example 2: Synthesis of 9-(3-chloropropionamido)-1-azabenzanthrone

[0027] 1.0g (4mm) of 9-amino-1-azabenzanthrone was refluxed in 10ml of chloropropionyl chloride for 3-4 hours, cooled, filtered, washed with ether, and the filtrate was recrystallized with DMF-ethanol to obtain yellow needles (compound 2) 1.0 g (about 74% yield). 1 H NMR (DMSO, 300 MHz): δ2.92 (t, 2H, J = 6.2Hz), 3.93 (t, 2H, J = 6.2Hz), 7.98 (d, 1H, J = 5.6Hz), 8.01-8.11 (m, 2H), 8.42(d, 1H, J=8.2Hz), 8.54-8.56(m, 2H), 8.73-8.78(m, 2H), 10.55(s, 1H-CONH); ESI-MS m / z: 338 [M+H] + .

[0028] The synthetic compound 2 structural formula is as follows:

[0029]

Embodiment 3

[0030] Example 3: Synthesis of 9-(4-chlorobutanylamino)-1-azabenzanthrone

[0031] 1.0g (4mm) of 9-amino-1-azabenzanthrone was refluxed in 10ml of chlorobutyryl chloride for 2.5 hours, cooled, filtered, washed with ether, and the filtrate was recrystallized with DMF-ethanol to obtain yellow needle-like crystals (Compound 3) 1.0 g (about 74% yield). 1 H NMR (DMSO, 300MHz): δ2.09(m, 2H), 2.58(t, 2H, J=7.3Hz), 3.74(t, 2H, J=6.5Hz), 7.98(d, 1H, J=5.6 Hz), 8.01-8.10(m, 2H), 8.41(d, 1H, J=8.1Hz), 8.54-8.56(m, 2H), 8.72-8.78(m, 2H), 10.46(s, 1H-CONH) ;ESI-MS m / z: 352[M+H] + .

[0032] The synthetic compound 3 structural formula is as follows:

[0033]

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Abstract

The present invention is one kind of 9-aminoalkylamido-1-azabenzanthrone derivative and its synthesis process and application as acetylcholinesterase inhibitor. Experiment shows that 9-aminoalkylamido-1-azabenzanthrone derivative of the present invention has powerful acetylcholinesterase inhibiting performance and excellent inhibiting selectivity, and its inhibiting capacity on acetylcholinesterase is over 1000 times higher than that on butyrylcholinesterase. It is shown that the said compound may be developed into medicine for treating Alzheimer disease, cerebrovascular dementia and similar diseases.

Description

technical field [0001] The present invention relates to a class of 9-aminoalkanoyl amido-1-azabenzanthrone derivatives, their synthesis method and their use as acetylcholinesterase inhibitor drugs, such as for preparing and treating Alzheimer's disease (Alzheimer Disease , AD) and diseases such as cerebrovascular dementia. Background technique [0002] Acetylcholinesterase (AChE) is a key enzyme in biological nerve transmission. In cholinergic synapses, this enzyme degrades acetylcholine, terminates the excitatory effect of neurotransmitter acetylcholine on the postsynaptic membrane, and ensures that nerve signals are Normal transmission in living organisms. Cholinesterase is divided into acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) according to the specificity of its catalytic substrate. AChE, known as true or specific cholinesterase, is the most important hydrolase for maintaining cholinergic nerve impulses in the body. BuChE is known as pseudo or nonsp...

Claims

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Application Information

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IPC IPC(8): C07D221/18C07D401/12A61K31/473A61P25/28A61P27/06A61P21/04
Inventor 古练权唐煌黄志纾魏涌标宁方贤黄世亮
Owner SUN YAT SEN UNIV
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