Benzofuran category compound, its preparing method and usage

A technology of benzopyran and compounds, which is applied in the preparation of anti-type II diabetes drugs and the synthesis of benzopyran compounds, which can solve the problems of high liver toxicity

Inactive Publication Date: 2003-10-01
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1997, troglitazone, the first thiazolidinedione insulin sensitizer, was launched on the market. This drug and its similar drugs, pioglitazone and rosiglitazone, which were later marketed, can control blood sugar well in clinical practice. , but thiazolidinediones have shown varying degrees of liver toxicity after their marketing [Henry, R.R.Endocrinol.Metab.Clin.North Am.1997, 26, 553], among which troglitazone withdrawn from the market

Method used

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  • Benzofuran category compound, its preparing method and usage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Example 1: 7-Benzyloxy-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester (compound 1)

[0129]7-Hydroxy-3-coumarin carboxylate methyl ester (0.2g, 1mmol) was dissolved in N,N'-dimethylformamide (2mL), added benzyl bromide (0.36ml, 3mmol) and finely ground carbonic acid Potassium (0.5g), stirred at 70°C for 12 hours. Add water (10 mL), extract with ethyl acetate (2×10 mL), combine ethyl acetate, wash with water, and dry over anhydrous sodium sulfate. Concentrate under reduced pressure to about 5 mL. A solid precipitated after standing, and was filtered with suction to obtain 0.21 g of the title compound, with a yield of 67.7%. m.p.129-130°C. 1 H NMR (CDCl 3 ): δ=3.92(s, 3H), 5.19(s, 2H), 6.85(d, J=2.4Hz, 1H), 6.95(dd, J=8.8Hz, 2.4Hz, 1H), 7.40(m, 5H ), 7.52(d, J=8.8Hz, 1H), 8.55(s, 1H); elemental analysis, C 18 h 14 o 5 (310): calculated value C, 69.68; H, 4.52. found value C, 69.63; H, 4.51; , 1026, 794.5, 725.1, 692.3, 636.4cm -1 ; EI-MS (m / z): 310 (12, M ...

Embodiment 2

[0130] Example 2: 7-Benzyloxy-2-oxo-2H-1-chromene-3-carboxylic acid (Compound 2)

[0131] Compound 1 (0.1 g, 0.32 mmol) was dissolved in ethanol (0.5 mL), 10% aqueous sodium hydroxide solution (0.5 mL) was added, and the reaction was refluxed for 1 hour. After cooling, add concentrated hydrochloric acid (0.3 mL), continue stirring for 10 minutes, add water (5 mL), suction filter the produced solid, wash the filter cake with water, and dry to obtain the title compound 0.09 g, yield 90%. m.p.196-197°C. 1 H NMR (DMSO-d6): δ=5.25(s, 2H), 7.08(dd, J=2.2Hz, 8.8Hz, 1H), 7.12(d, J=2.2Hz, 1H), 7.30-7.50(m, 5H), 7.83(d, J=8.8Hz, 1H), 8.73(s, 1H); elemental analysis, C 17 h 12 o 5 (296): Calculated C, 68.92; H, 4.05; Found C, 68.50; H, 4.12; cm -1 ; EI-MS (m / z): 296 (4, M + ), 91(100).

Embodiment 3

[0132] Example 3: Methyl 7-(2-phenyl)ethoxy-2-oxo-2H-1-benzopyran 3-carboxylate (Compound 3)

[0133] Dissolve methyl 7-hydroxy-3-coumarincarboxylate (0.6g, 3mmol) and 2-phenylethanol (0.36mL, 3mmol) in anhydrous tetrahydrofuran (60mL), add triphenylphosphine (1.2g , 4.5mmol), diethyl azodicarboxylate (0.72mL, 4.5mmol) was slowly added dropwise at 0°C, and stirred at room temperature for 24 hours. The solvent was distilled off under reduced pressure, and the residue was precipitated in methanol as a white solid, which was recrystallized from methanol to obtain 0.45 g of the title compound, with a yield of 46.3%. m.p.100-101°C. 1 H NMR (CDCl 3 ): δ=3.12(t, J=6.8Hz, 2H), 3.92(s, 3H), 4.14(t, J=7.1Hz, 2H), 6.79(d, J=2.4Hz, 1H), 6.88(dd , J=2.4Hz, 8.8Hz, 1H), 7.21-7.35(m, 5H), 7.47(d, J=8.7Hz, 1H), 8.50(s, 1H); elemental analysis, C 19 h 16 o 5 (324): calculated value C, 70.37; H, 4.94. found value C, 70.25; H, 4.93; , 1114.7, 1018.2, 835, 749.5, 738.6, 700, 594cm -1 ; EI-...

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Abstract

A benzopyran compound or its salts, their preparing process and their application in preparing medicine for treating B-type diabetes are disclosed.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and endocrine therapy, in particular to the synthesis of benzopyran compounds and their use in the preparation of anti-II diabetes drugs. Background of the invention [0002] Type II diabetes mellitus is a metabolic disorder, and the patients mainly manifest as elevated blood glucose concentration (fasting blood glucose concentration greater than 130 mg / dL) and diabetes. Sustained hyperglycemia can lead to many complications, such as retinal, renal, and nervous system lesions, especially cardiovascular complications are the main cause of death and disability in diabetic patients [Shinkai, H.Exp.Opin.Ther.Patents.2000, 10:596]. Therefore, it is extremely important to control the patient's blood sugar level to delay or block the occurrence of complications. At present, sulfonylureas, drugs that promote insulin secretion, and biguanides are mainly used clinically to control blood sugar in patien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/352A61K31/404A61K31/422A61K31/4433A61P3/10C07D311/20C07D405/12C07D413/12
Inventor 杨玉社汤磊嵇汝运陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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