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Nitric oxide-donating chrysin derivatives, preparation method thereof, medical use thereof

A technology of nitric oxide and chrysin, which is applied in the field of diabetic cardiovascular complications, metabolic syndrome and related diseases, nitric oxide donor chrysin derivatives, and the treatment of diabetes

Inactive Publication Date: 2010-07-07
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This combination of new drugs mainly includes nitrosothiol / drug conjugates; nitrate / drug conjugates; furazan nitrogen oxide / drug conjugates, many of which have been patented and used clinically

Method used

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  • Nitric oxide-donating chrysin derivatives, preparation method thereof, medical use thereof
  • Nitric oxide-donating chrysin derivatives, preparation method thereof, medical use thereof
  • Nitric oxide-donating chrysin derivatives, preparation method thereof, medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061]

[0062] Chrysin (1) 0.01mol, anhydrous potassium carbonate 0.005mol and acetone 150ml, heated to boiling until the solution becomes clear, then add 0.05mol of 1,2-dibromobutane dropwise, and reflux for 24h. Suction filtration, take the filtrate and concentrate to obtain a yellow solid, wash the solid with petroleum ether, 1% sodium hydroxide, wash several times with water, and dry to obtain the intermediate product, light yellow solid (2); yield 74.5%, mp 146 ~147℃. 1 H NMR(CDCl 3 )δ(ppm): 12.71(s, 1H), 7.87~7.89(m,2H), 7.52~7.56(m,3H), 6.74(s,1H), 6.49~6.50(d,1H), 6.361~6.367 (d, 1H), 4.07 to 4.10 (m, 2H)), 3.48 to 3.51 (m, 2H), 1.98 to 2.12 (m, 4H). The intermediate product (2) 0.005mol and 50ml of anhydrous acetonitrile were heated to 50°C, and 20ml of acetonitrile solution containing 0.025mol of silver nitrate was added, and the temperature was continued to rise to 70°C and reacted for 1h in the dark. The silver bromide precipitate was removed by suction filtration...

Embodiment 2

[0064]

[0065] Chrysin (1) 0.01mol, anhydrous potassium carbonate 0.005mol and acetone 150ml, heated to boiling until the solution becomes clear, add bromoacetate, 0.02mol, and reflux for 24h. After suction filtration, the filtrate was concentrated to obtain a yellow solid. The solid was washed with petroleum ether, 1% sodium hydroxide, washed with water several times, and dried to obtain a light yellow solid (5). The yield was 71%. mp160°C. 1 H NMR(CDCl 3 )δ(ppm): 12.75(s, 1H), 7.87-7.89(m, 2H), 7.51-7.57(m, 3H), 6.68(s, 1H), 6.52-6.53(d, 1H), 6.372-6.377 (d, 1H), 4.7 (s, 2H), 4.27-4.32 (m, 2H), 1.30-1.34 (m, 3H). Use 0.005 mol of this light yellow solid (5), 30 ml of methanol, and 0.032 mol of potassium hydroxide, heat to reflux, and stir for 8 hours to obtain a yellow solid insoluble in methanol. Distill the methanol out under reduced pressure, add water to dissolve, adjust the PH to 2 with 1mol / L hydrochloric acid. A yellow solid was obtained by suction filtration, washe...

Embodiment 3

[0067]

[0068] Suspend 0.005mol of 7-carboxymethylchrysin (6) in 60ml of anhydrous dichloromethane, furoxan oxide (10) 0.005mol, DCC, 0.005mol and DMAP 0.002mol, and stir overnight at 25°C to form a white precipitate . The precipitate was filtered off, and the filtrate was concentrated to a dark yellow slightly sticky solid. Add appropriate amount of dichloromethane to dissolve, then add petroleum ether to precipitate a light yellow powdery solid, and wash with 5% potassium carbonate solution and water 3 times each, dry the obtained solid and recrystallize it with ethyl acetate-petroleum ether to give a light yellow Solid (9). The yield is 63%, mp174-175℃, 1 H NMR (CDCl3) δ (ppm): 12.76 (s, 1H), 7.87-7.89 (m, 2H), 7.63-7.65 (m, 2H), 7.49-7.57 (m, 6H), 6.68 (s, 1H) , 6.46-6.47 (d, 1H), 6.32-6.33 (d, 1H), 5.31 (s, 2H), 4.76 (s, 2H).

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Abstract

The invention relates to the fields of pharmaceutical chemistry and particularly provides a series of nitric oxide-donating chrysin derivatives, which are prepared by modifying the chrysin at position 5 and position 7. The nitric oxide-donating chrysin derivatives release nitric oxide and chrysin derivatives in vivo and therefore can conduct functions of reducing blood sugar and blood pressure, promoting angiogenesis, improving a vascular endothelial function and lipid metabolism disorders and can be used in the preparation of medicaments for treating diabetes, diabetic cardiovascular complications, metabolic syndrome and endothelial dysfunction.

Description

Technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to nitric oxide donor chrysin derivatives, their preparation methods, and the medical use of these compounds, especially as drugs for the treatment of diabetes, diabetic cardiovascular complications, metabolic syndrome and related diseases the use of. Background technique [0002] Flavonoids are a class of low-molecular-weight natural plant components, which are widely found in vegetables, fruits and medicinal plants, with small side effects and extensive pharmacological effects. It can prevent and treat diabetes by means of anti-oxidation, inhibition of α-glucosidase, insulin-like effect, inhibition of the absorption of sugar in the small intestine, and anti-viral infection, and can resist platelet aggregation, microangiopathy and protein non-enzymatic glycosylation Play a role in preventing and treating diabetes complications. [0003] Chrysin is a kind of flavonoids with the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D413/12A61K31/352A61P3/10A61P9/00
Inventor 邹晓青彭圣明李元建姜德建邓汉武
Owner CENT SOUTH UNIV
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