Rutin aliphatic ester derivatives, preparation method and application thereof

A technology of fatty acid esters and derivatives, applied in the field of rutin derivatives, can solve the problems of low bioavailability, insoluble in fat, poor absorption, etc., achieve the effect of simple preparation method, low price, and improved absorption rate

Inactive Publication Date: 2010-05-12
上海双科医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although the above-mentioned rutin can prepare anti-cardiovascular and cerebrovascular diseases and anti-hepatitis B virus drugs, because rutin is almost insoluble in water and hardly soluble in fat, it is poorly absorbed in the intestinal tract after oral administration and has low bioavailability

Method used

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  • Rutin aliphatic ester derivatives, preparation method and application thereof
  • Rutin aliphatic ester derivatives, preparation method and application thereof
  • Rutin aliphatic ester derivatives, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of embodiment 1 rutin palmitate

[0036]

[0037] Dissolve 0.1mol rutin and 0.5mol palmitic acid in 500ml of tert-butanol, heat, add 2.5g of lipase Novozym435 at 60°C, stir, and react for 10 hours, add 50g of 3A molecular sieve, react for 96 hours, filter to remove molecular sieve and Enzyme, the solution was evaporated to dryness under reduced pressure, and the residue was subjected to silica gel column chromatography, eluent: ethyl acetate-methanol mixture (weight ratio 10:1), the product components were collected, and the solvent was evaporated to dryness to obtain rutin palmitate. Yield 70%. The following spectral data are shown for rutin palmitate.

[0038] Mp: 210-213°C. Electrospray mass spectrometry (ESI-MS) m / z: 871.5 [M+Na].

[0039] 1 H-NMR (C 5 D. 5 N): δ7.53 (2H, m, H-2' and H-6'), 6.79 (1H, d, J=9Hz, H-5'), 6.29 (1H, s, H-8), 6.12 (1H, s, H-6), 5.32 (1H, d, J=7.4Hz, H-1"), 4.65 (1H, t, J=9Hz, H-4'"), 4.48 (1H, s, H-1'"), 3.72-2.65 ...

Embodiment 2

[0041] The synthesis of embodiment 2 rutin myristate

[0042]

[0043] Dissolve 0.1mol of rutin and 0.15mol of myristic acid in 500ml of tert-butanol, heat, add 2.8g of lipase Novozym 435 at 75°C, stir, react for 8 hours, add 40g of 3A molecular sieve, react for 90 hours, filter to remove Molecular sieves and enzymes, the solution was evaporated to dryness under reduced pressure, the residue was subjected to silica gel column chromatography, eluent: ethyl acetate-methanol mixture (weight ratio 12:1), the product components were collected, the solvent was evaporated to dryness, and rutin nutmeg was obtained. Ester, yield 75%. The following spectral data are shown for rutin myristate.

[0044] Mp: 218-220°C. ESI-MS m / z: 843.5 [M+Na].

[0045] 1 H-NMR (C 5 D. 5 N): δ7.52 (2H, m, H-2' and H-6'), 6.78 (1H, d, J=9Hz, H-5'), 6.27 (1H, s, H-8), 6.14 (1H, s, H-6), 5.34 (1H, d, J=7.4Hz, H-1"), 4.67 (1H, t, J=9Hz, H-4'"), 4.49 (1H, s, H-1'"), 3.71-2.63 (9H, m, H2"-H6", H2'"-H5...

Embodiment 3

[0047] Example 3 Synthesis of rutin linolenate

[0048]

[0049] Dissolve 0.2 mol of rutin and 0.6 mol of linolenic acid in 800 ml of tert-butanol, heat, add 4 grams of lipase Novozym435 at 70 ° C, stir, and react for 10 hours, add 100 grams of 3A molecular sieves, react for 100 hours, filter to remove molecular sieves and Enzyme, the solution was evaporated to dryness under reduced pressure, and the residue was subjected to silica gel column chromatography, eluent: ethyl acetate-methanol mixture (weight ratio 15:1), the product components were collected, and the solvent was evaporated to dryness to obtain rutin linolenate. Yield 71%. The following spectral data are shown for rutin linolenate.

[0050] Mp: 202-204°C. ESI-MS m / z: 893.6 [M+Na].

[0051] 1 H-NMR (C 5 D. 5N): δ7.55 (2H, m, H-2' and H-6'), 6.83 (1H, d, J=9Hz, H-5'), 6.27 (1H, s, H-8), 6.11 (1H, s, H-6), 5.34 (1H, d, J=7.4Hz, H-1"), 4.61 (1H, t, J=9Hz, H-4'"), 4.43 (1H, s, H-1'"), 3.71-2.63 (9H, m, H2"-H6...

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Abstract

The invention provides rutin aliphatic ester derivatives, which are prepared by chemically synthesizing rutin and the aliphatic ester. The rutin aliphatic ester derivatives have an easily-obtained raw material, low cost, simple preparation method and high yield, and are suitable for industrialized production. The pharmacological test shows that the rutin aliphatic ester derivatives have obvious effect for inhibiting platelet aggregation and inhibiting the activity of hepatitis virus, and can be used for preparing an anti-angiocardiopathy medicine, an anti-cerebrovascular disease medicine, an anti-viral hepatitis B medicine and an anti-hepatitis C medicine.

Description

technical field [0001] The invention relates to rutin derivatives, in particular to rutin fatty acid ester derivatives and their preparation methods, and their application in the preparation of anti-cardiovascular and cerebrovascular disease drugs and antiviral hepatitis drugs. Background technique [0002] With the improvement of living standards, cardiovascular and cerebrovascular diseases have become a major threat to health. Nearly 3 million people die from cardiovascular and cerebrovascular diseases in my country every year, accounting for 51% of the total annual death causes in my country. And 75% of patients who survived lost their ability to work to varying degrees. The pathogenesis of many cardiovascular and cerebrovascular diseases such as thrombosis, atherosclerosis, inflammatory response, ischemia and reperfusion free radical injury are closely related to the mediation of platelet activating factor (PAF). [0003] Rutin has the effect of antagonizing PAF (Chen W...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C12P19/60A61K31/7048A61P9/00A61P31/14A61P7/02A61P31/12A61P31/20
Inventor 徐从立黄山
Owner 上海双科医药科技有限公司
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