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Application of 2-gylcosyl chinoline compound in preparing acetylcholine esterase resisting medicines

The technology of acetylcholinesterase and glycosyl quinoline is applied in the application field of 2-glycosyl quinoline compounds in the preparation of anti-acetylcholinesterase drugs, and achieves the effects of high bioavailability, strong solubility and broad application prospects

Inactive Publication Date: 2013-10-09
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nagarajan et al disclosed a one-pot synthesis method for 2-glycosyl quinoline compounds in Carbohydrate Research [J]. Esterase drugs have not been reported

Method used

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  • Application of 2-gylcosyl chinoline compound in preparing acetylcholine esterase resisting medicines
  • Application of 2-gylcosyl chinoline compound in preparing acetylcholine esterase resisting medicines
  • Application of 2-gylcosyl chinoline compound in preparing acetylcholine esterase resisting medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The synthesis of embodiment 1 intermediate β-D-acetonyl glucoside

[0025] Preparation route:

[0026]

[0027] Weigh 1~5g of D-glucose and 0.5~2.5g of sodium bicarbonate into a round bottom flask, add distilled water and stir at room temperature for 10~30min, then add 1~5g of acetylacetone and stir in an oil bath at 50~120℃ Under the reaction 2 ~ 10h. Stop the reaction, cool and then extract with carbon dichloride, adjust the pH to 7 with dilute hydrochloric acid, remove water under reduced pressure and then add methanol, the inorganic salt precipitates because it is insoluble in methanol, and can be removed by filtration (or through a silica gel column). The product can be obtained by removing the solvent under reduced pressure. The yield is about 77%, m.p: 122-124°C.

Embodiment 2

[0028] Embodiment 2, the synthesis of compound A1

[0029] Preparation route:

[0030]

[0031] Weigh 0.5 mmol of 2-aminobenzaldehyde and 0.5 mmol of β-acetonyl glucoside into a round bottom flask, add methanol, and stir at room temperature to dissolve them. Add 25 mol% pyrrolidine (relative to 2-aminobenzaldehyde), and follow the reaction with TLC in an oil bath at 60-120°C until the reaction remains unchanged. The reaction was stopped and cooled, and the solvent in the reaction was removed under reduced pressure, and the pure product was obtained by passing through the column with ethyl acetate:isopropanol:water=16:2:1 (v / v / v).

[0032] White solid; m.p: 257-258°C; IR (KBr, cm -1 ): 3482(vs), 3385(s), 3329(s), 3104(m), 2908(m), 1601(m), 1563(w), 1427(m), 1298(s), 1127(m ), 1088(vs), 1033(s), 838(m), 763(m); 1 H NMR (DMSO-d 6 ): δ8.23(dd, J=2.8Hz, J=5.2Hz, 1H, Ar-H), 7.94(t, J=7.2Hz, 2H, Ar-H), 7.72(s, 1H, Ar-H ), 7.55(d, J=8.0Hz, 2H, Ar-H), 5.20(s, 1H), 5.00(s, 1H),...

Embodiment 3

[0033] The synthesis of embodiment 3 compound A2

[0034] The preparation method is the same as in Example 2, except that 3,6-dimethoxy-2-aminobenzaldehyde is used instead of 2-aminobenzaldehyde to obtain compound A2.

[0035]

[0036] White solid; m.p: 121-122°C; IR (KBr, cm -1 ): 3522(s), 3268(s), 2871(s), 1619(s), 1604(s), 1346(s), 1263(vs), 1117(vs), 1090(vs), 1043(s) ), 908(m), 723(m); 1 H NMR (DMSO-d 6 ): δ8.33(s, 1H, Ar-H), 7.52(s, 1H, Ar-H), 7.02(s, 1H, Ar-H), 6.85(s, 1H, Ar-H), 5.25( s, 1H), 4.96(s, H), 4.88(s, 1H), 4.30(s, 1H), 4.15(s, 1H), 3.89(s, 3H), 3.88(s, 3H), 3.17(s , 2H), 3.09-2.97(m, 3H), 2.87(d, J=8.0H, 1H);13 C NMR (DMSO-d 6 ): δ164.6, 153.9, 153.2, 144.5, 135.0, 127.5, 124.4, 113.1, 108.7, 85.7, 84.5, 79.3, 75.5, 66.4, 60.9, 60.8.0, 46.5; ESI-MS m / z calcd for C 18 h 23 NO 7 ([M+1] + ): 365.15, Found: ([M+1] + ): 366.44, ([M+23] + ): 388.32, ([2M+23] + ): 752.87; Anal.Calcd for C 18 h 23 NO 7 : C, 59.17; H, 6.34; N, 3.83; Found: C, 59.25...

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Abstract

The invention discloses application of 2-gylcosyl chinoline compound in preparing acetylcholine esterase resisting medicines. The 2-gylcosyl chinoline compound is of a structural formula as shown in formula (I), wherein R1, R2, R3 and R4 independently choose -H, -OCH3 or -Br. A preparation method of the 2-gylcosyl chinoline compound can be produced according to the prior art. The 2-gylcosyl chinoline compound is strong in dissolubility in water, high in biological utilization, strong in restrain activity on acetylcholine esterase and wide in application prospect on preparing acetylcholine esterase resisting medicines. The 2-gylcosyl chinoline compound is simple in preparation path, low in cost, small in environment pollution and suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the fields of medicine and chemical industry, and in particular relates to the application of a 2-glycosyl quinoline compound in the preparation of anti-acetylcholinesterase drugs. Background technique [0002] Alzheimer's disease (AD), also known as senile dementia or Alzheimer's disease, is a central nervous system degenerative disease mainly characterized by progressive cognitive impairment and memory impairment. The main clinical manifestations of the disease are memory loss, persistent cognitive decline, movement disorders, and gradual loss of independent living ability in severe cases, accompanied by a series of psychiatric symptoms. Prevalence studies put the number of Alzheimer's cases in the United States at 4.5 million in 2000. For every 5-year increase in age, the percentage of patients with Alzheimer's disease will double. At present, AD disease has become the second largest disease that threatens the health of mi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/4709A61P25/28
Inventor 龙玉华张寒梅刘真权周亭邹致富
Owner SOUTH CHINA NORMAL UNIVERSITY
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