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Amidocyanogen amido xanthone pyridine derivant, and preparation method and application thereof

A kind of technology of xanthone and pyridine, applied in the field of aminoalkylamido xanthone and pyridine derivatives and preparation thereof

Inactive Publication Date: 2011-04-27
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these cholinesterase inhibitor drugs can only relieve symptoms for a short time and are accompanied by relatively large side effects and other defects. It has been the direction of researchers' efforts to seek new cholinesterase inhibitors with low side effects and good curative effect.

Method used

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  • Amidocyanogen amido xanthone pyridine derivant, and preparation method and application thereof
  • Amidocyanogen amido xanthone pyridine derivant, and preparation method and application thereof
  • Amidocyanogen amido xanthone pyridine derivant, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of 2-(quinoline-8-oxyl group)-benzoic acid (compound 1)

[0036] 1.24g (5mmol) of o-iodobenzoic acid, 5mL of n-amyl alcohol, mix and stir until o-iodobenzoic acid is completely dissolved; then add 1.38g (10mmol) of anhydrous potassium carbonate, and under vigorous stirring, add 0.726g (5mmol) of 8-hydroxyquinoline, 0.0635g (1mmol) of copper powder and 0.190g (1mmol) of cuprous iodide were then stirred and refluxed at 160°C for 2.5h. The reaction liquid was poured into 200mL hot water, and suction filtered while it was hot to obtain dark yellow solid and light green mother liquor. The filtrate was cooled to room temperature, extracted with chloroform, the organic layer was washed with saturated potassium carbonate aqueous solution (15×3mL), the aqueous layer and the potassium carbonate washing solution were combined, and the pH value was adjusted to 1-2 with dilute hydrochloric acid, a large amount of precipitates were precipitated, and stood overnig...

Embodiment 2

[0040] Example 2: Synthesis of 7H-pyrido[4,3-c]xanthen-7-one (Compound 2)

[0041] Polyphosphoric acid (PPA) 3.5g, heated to 75°C in an oil bath, added 0.50g of compound 1 with stirring, heated to 140°C, heated and stirred for 2h. The reaction mixture was poured into 200 mL of ice water while it was hot, and the pH value was adjusted to 7-8 with concentrated ammonia water, and a large amount of white flocculent precipitates were precipitated. Cool, filter with suction, and dry to obtain 0.414g of solid. The crude yield is 88.1%. The crude product was recrystallized twice from methanol to obtain 0.39 g of light yellow needle crystals with a yield of 83.0%.

[0042] m.p.220~221℃; 1 H NMR (CDCl 3 , 500MHz) δ: 9.16(dd, J=1.1, 4.1Hz, 1H), 8.42(dd, J=1.4, 8.0Hz, 1H), 8.40(d, J=8.7Hz, 1H), 8.29(dd, J =1.1, 8.3Hz, 1H), 7.92(d, J=8.4Hz, 1H), 7.82(m, 1H), 7.74(d, J=8.7Hz, 1H), 7.66(dd, J=4.2, 8.3Hz , 1H), 7.48 (t, J=7.5Hz, 1H); IR (KBr) v: 2926, 1650, 1633, 1609, 1507, 1464, 1452,...

Embodiment 3

[0045] Example 3: Synthesis of 9-nitro-7H-pyrido[4,3-c]xanthene-7-one (compound 3)

[0046] Concentrated sulfuric acid 15mL, cooled with ice brine for 5min, added 0.61g (6mmol) KNO 3 , stirred until completely dissolved, kept the temperature at 0-5 °C, added 1.24 g (5 mmol) of compound 2 in batches, stirred at a temperature of 0-5 °C for 30 min, and slowly raised the temperature to room temperature and stirred for 3 h. Pour the reaction solution into 100mL of ice water with stirring, and a large amount of white flocculent precipitates precipitate out; adjust the pH value to 8-9 with concentrated ammonia water, cool to room temperature, filter with suction, wash with water, dry, and recrystallize nitrobenzene to obtain white Solid 1.35g, yield 96%.

[0047] m.p.>300℃; 1 H NMR (DMSO-d 6 , 500MHz) δ: 9.21(dd, J=1.4, 4.1Hz, 1H), 8.97(d, J=2.8Hz, 1H), 8.71(dd, J=2.9, 9.0Hz, 1H), 8.65(dd, J =1.4, 8.3Hz, 1H), 8.28(d, J=8.6Hz, 1H), 8.20(d, J=9.2Hz, 1H), 8.08(d, J=8.7Hz, 1H), 7.91(...

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Abstract

The invention discloses amidocyanogen amido xanthone pyridine derivant and the preparation method thereof. The derivant has the general expression (I) structure, wherein R<1> is -NHCO(CH2)nR<2> or H, and n ranges from 1 to 3. The derivant can be used for acetylcholinesterase inhibitor medicines, for instance the derivant can be used for preparing medicines for treating Alzheimer's disease, cerebral vascular dementia, glaucoma or myasthenia gravis pseudoparalytica.

Description

technical field [0001] The present invention relates to aminoalkanoamido xanthonopyridine derivatives and a preparation method thereof. The derivatives can be used as acetylcholinesterase inhibitors for the treatment of Alzheimer's disease (Alzheimer Disease, AD) and cerebrovascular dementia and other diseases. Background technique [0002] Acetylcholinesterase (AChE, EC 3.1.1.7.), also known as acetylcholinehydrolase, its main biological function is to rapidly hydrolyze the neurotransmitter acetylcholine (ACh) at cholinergic synapses. , so as to stop the transmission of nerve impulses. Its reaction formula is as follows: [0003] [0004] Butyrylcholinesterase (butyrylcholinesterase, BChE, EC 3.1.1.8), also known as pseudo or non-specific cholinesterase, is an enzyme that hydrolyzes butyrylcholine. It belongs to the serine esterase family, mainly distributed in serum and liver, and also exists in a small amount in muscle and brain tissue. BChE can hydrolyze many este...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052A61K31/4741A61K31/5377A61P25/28A61P27/06A61P21/04
Inventor 覃江克韩留玉杨政敏兰文丽唐煌苏桂发
Owner GUANGXI NORMAL UNIV
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