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C-glycoside and C-glycoside compound containing substituted aromatic rings as well as preparation and use thereofb

A technology of compound and sugar carbon glycosides, which is applied in the field of medicine, can solve the problem of nerve damage without therapeutic effect

Inactive Publication Date: 2008-09-03
INST OF RADIATION MEDICINE ACAD OF MILITARY MEDICAL SCI OF THE PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the existing anti-myocardial ischemic drugs have no therapeutic effect on nerve damage caused by cerebral ischemia and hypoxia

Method used

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  • C-glycoside and C-glycoside compound containing substituted aromatic rings as well as preparation and use thereofb
  • C-glycoside and C-glycoside compound containing substituted aromatic rings as well as preparation and use thereofb
  • C-glycoside and C-glycoside compound containing substituted aromatic rings as well as preparation and use thereofb

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: (3',4',5'-trimethoxyphenyl)methyl-1-thio-β-D-glucopyranoside (S01)

[0030] A: (3′,4′,5′-trimethoxyphenyl)methyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

[0031] 1.31g (5mmol) 1-bromomethyl-3,4,5-trimethoxybenzene and 1.82g (5mmol) 2,3,4,6-tetra-O-acetyl-β-D-1-sulfur Dissolve glucopyranose in 30mL of acetone, add 0.69g (5mmol) of anhydrous potassium carbonate, and heat to reflux for 6h. After cooling, filter, wash the solid with acetone, and concentrate the filtrate to remove the solvent to obtain 2.70 g of syrup, and the yield of the crude product is 99.2%. R f =0.25, petroleum ether (60-90°C):ethyl acetate=2:1.

[0032] B: (3′,4′,5′-trimethoxyphenyl)methyl-1-thio-β-D-glucopyranoside (S01)

[0033] 2.70g (4.96mmol) of (3',4',5'-trimethoxyphenyl)methyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D- Glucopyranoside was dissolved in 30 mL of methanol, 4.14 g (30 mmol) of anhydrous potassium carbonate was added, and the reaction was stirred at room temperatur...

Embodiment 2

[0034] Example 2: (4'-methylphenyl)methyl-1-thio-β-D-glucopyranoside (S02)

[0035] A: (4′-methylphenyl)methyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

reference example 1

[0036] Reference Example 1 Step A reaction synthesis, to obtain 2.20g syrup, crude product yield 94.0%. R f =0.71, petroleum ether (60-90°C):ethyl acetate=2:1.

[0037] B: (4′-methylphenyl)methyl-1-thio-β-D-glucopyranoside (S02)

[0038] Reference Example 1 Step B reaction synthesis, prepared 1.17g syrup, yield 83.0%. 1 HNMR (CD 3 OD) δ (ppm): 2.29 (3H, s, -CH 3 ), 3.17-3.31 (4H, H-5, H-4, H-3, H-2), 3.65 (1H, dd, H-6a, J 1 =6.2Hz,J 2 = 12.2Hz), 3.79 (1H, d, -CHPh', J = 13.2Hz), 3.88 (1H, dd, H-6b, J 1 =2.2Hz,J 2= 12.2Hz), 3.99 (1H, d, -CHPh', J = 13Hz), 4.13 (1H, d, H-1, J = 9.6Hz), 7.10 (2H, d, Ph', J = 7.8Hz) , 7.22 (2H, d, Ph', J = 8.1 Hz). -c ESI m / z: 299(M-1), 359(M+Na+2H 2 O), 599(2M-1).

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Abstract

The invention discloses C-glycoside with substituted aromatic ring, S-glycoside compounds, pharmaceutical compositions with effective dose compounds, and applications of the compounds and compositions for preparing cardio-cerebrovascular anti-hypoxic ischemia medicine and neuroprotection medicine. In the compounds are c-glycoside compounds when X represents CH2, wherein when Y represents CH2, n may be 0 or 1, when n is 0, m is 0, and when n is 1, m is 0 or 1; when Y represents NH, n=m=1; when X represents S, the compounds is S-glycoside compounds, wherein Y represents CH2, n may be 1, 2 or 3, and m is 0; R represents mono-substituted, disubstituted, tri-substituted hydrogen C1-C3 straight-chain or branched chain alkyl and hydroxyl, or C1-C3 straight-chain or carboxylic acid ester. 14 compounds found have better protective action to hypoxia-reoxygenation injury of myocardium than or equal to salidroside; 15 compounds have stronger neuroprotection activity than or equal to gastrodine.

Description

technical field [0001] The present invention belongs to the field of medicine, and relates to a drug for treating cardiovascular and cerebrovascular diseases, in particular to a class of glycosides and glucosinolate compounds (I) substituted with aromatic rings and their pharmaceutical compositions, and the compounds and compositions in the treatment of cardiovascular and cerebrovascular diseases. Applications in the field of anti-ischemic hypoxia and neuroprotection. Background technique [0002] Cardiovascular and cerebrovascular diseases have been on the rise year by year in my country in recent years, and have become the leading cause of death among adults in my country. Analyze the progress of this type of disease, among them, transient cerebral ischemia, due to insufficient cerebral blood supply, can cause temporary dysfunction, and repeated attacks can develop into complete stroke; coronary artery disease can cause myocardial ischemia and hypoxia, Angina pectoris occ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H5/10C07D309/10A61K31/7028A61K31/351A61P9/10A61P25/00
Inventor 彭涛王林韩凤昭温晓雪张首国刘靖张熙
Owner INST OF RADIATION MEDICINE ACAD OF MILITARY MEDICAL SCI OF THE PLA
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