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Thioglycosidic sterol glycoside and thioglycosidic stanol glycoside, preparation method and application thereof

A technology of thioglycosidic bond stanol glycosides and thioglycosidic bond sterol glycosides is applied in metabolic diseases, steroids, organic chemistry, etc., and can solve the problems of lack of access means, short drug half-life, and inhomogeneous structure. To achieve the effect of simplifying the experimental scheme, improving stability, and increasing flexibility

Active Publication Date: 2022-05-03
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Purpose of the invention: Aiming at the limitations of the existing oxyglycoside sterol / stanol glycosides, the present invention provides a class of thioglycoside sterol glycosides or thioglycoside stanol glycosides, which solves the problem of the current low molecular weight acetyl sulfate The problems of heterogeneous structure of heparin, lack of means of obtaining, and short half-life of the drug

Method used

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  • Thioglycosidic sterol glycoside and thioglycosidic stanol glycoside, preparation method and application thereof
  • Thioglycosidic sterol glycoside and thioglycosidic stanol glycoside, preparation method and application thereof
  • Thioglycosidic sterol glycoside and thioglycosidic stanol glycoside, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Rapeseed sterol (compound 1) was used as raw material and total acetyl protected glucose (compound 5) was used as sugar donor

[0047] Synthesis of compound 2

[0048] Dissolve crude natural sterol compound 1 (rapeseed sterol, 0.7G, 1.68mmol) in anhydrous DCM (10ml) and anhydrous pyridine (0.24ml) pre cooled to 0 ℃, and then slowly add anhydrous DCM (3.5ml) solution containing trifluoromethylsulfonic anhydride (1.422g, 2.8mmol) to the solution of the above compound 1 drop by drop. The dropping time needs to exceed 30min, and when adding DCM, it is necessary to ensure that the system is 0 ℃, After dropping, the reaction system needs to react continuously at 0 ℃ for 1 hour. After the reaction, wash with saturated sodium bicarbonate solution (50 ml) and magnesium sulfate (MgSO) 4 ）After drying, filtration, evaporation and concentration, compound 2 (0.752g, 83%) substituted by trifluoromethylsulfonyl at position C-3 was obtained, 1H NMR (300MHz, DMSO) δ 1.24(m, 3H),1.90-1.65(m,...

Embodiment 2

[0058] Rapeseed oil stanol (compound 1) was used as raw material and total benzoyl protected glucose (compound 5) was used as sugar donor

[0059] Synthesis of compound 2

[0060] Dissolve crude natural sterol compound 1 (0.7G, 1.68mmol) in anhydrous DCM (10ml) and anhydrous pyridine (0.24ml) pre cooled to 0 ℃, and then slowly add anhydrous DCM (3.5ml) solution of trifluoromethyl sulfonic anhydride (1.422g, 2.8mmol) to the solution of compound 1 drop by drop. The dropping time needs to exceed 30min, and when DCM is added, it needs to ensure that the system is 0 ℃, and the reaction system needs to react continuously at 0 ℃ for 1 hour after dropping. After the reaction, wash with saturated sodium bicarbonate solution (50ml) and magnesium sulfate (MgSO 4 ）After drying, filtration, evaporation and concentration, compound 2 (0.730g, 81%) substituted by trifluoromethylsulfonyl at position C-3 was obtained, 1H NMR (300MHz, DMSO) δ 1.24(m,3H),1.90-1.65(m,2H),1.90-1.65(m,2H),4.73(m,1H),1.5...

Embodiment 3

[0070] The preparation method of example 3 is the same as that of example 1, except that compound 1 is rapeseed sterol, and the amount of trifluoromethyl sulfonic anhydride in step (1) is twice the number of moles of compound 1; The reaction was carried out at - 10 ℃; In step (2), the amount of potassium thioacetate is 1 times the number of moles of compound 2; The reaction was carried out at - 20 ℃; The reaction solvent used in step (3) is ethyl acetate; The reaction reagent used is potassium hydroxide, and the amount of basic reagent is 5 times the number of moles of compound 3; The reaction solvent used in step (4) is toluene, the Lewis acid catalyst used is trifluoromethane sulfonic acid, and the amount of Lewis acid catalyst is 0.5 times the number of moles of compound 3; The inert shielding gas is helium; In step (5), compound 6 is hydrolyzed and deprotected with alkali. The alkali is potassium hydroxide (KOH), the reaction solvent is ether, and the amount of alkaline reagen...

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Abstract

The invention discloses a class of thioglucoside-bonded sterol glycosides and thioglucoside-bonded stanol glycosides and their preparation methods and applications. The structures of thioglycoside-bonded sterol glycosides and thioglucoside-bonded stanol glycosides are respectively shown in formula I and Ⅱ, R in Ⅰ and Ⅱ 1 Indicates a carbon chain composed of 8‑10 carbon atoms. The invention develops and optimizes the substitution of trifluoromethanesulfonic anhydride on the C-3 position of sterols / stanols, and then realizes the substitution of C-3 sulfhydryl groups, and then utilizes fully protected glucose to realize the C-3-position sugar group Finally, the protective group can be removed under alkaline conditions to obtain thioglycosidic sterol / stanol glycosides. The entire synthetic process route is efficient and concise, and the thioglycosidic bond also improves the stability of the glycosidic bond and the stability and biological activity of the glycosylated product.

Description

technical field [0001] The invention belongs to glycosylated sterol / stanol, in particular to thioglycoside linked sterol glycoside and thioglycoside linked stanol glycoside, and a preparation method and application thereof. Background technology [0002] Phytosterols, also known as phytosterols, belong to steroids with plant active components. They are composed of three six membered rings and one five membered ring. There is a hydroxyl group at position C-3 and a side chain composed of 8-10 carbon atoms at position C-17. The one with double bond at C-5 position is called sterol, and the one with saturated C-5 position is called stanol. Common phytosterols include campesterol, sitosterol, stigmasterol and brassicasterol. Common phytosterols include campestanol, sitostanol, stigmastanol and brassicasterol. Phytosterol / stanol has the functions of inhibiting cholesterol absorption, anti-inflammatory and antipyretic, anti-oxidation, preventing and treating cardiovascular diseases,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J31/00A61P35/00A61P29/00A61P3/06A61P9/00A61P39/06
CPCC07J31/003A61P35/00A61P29/00A61P3/06A61P9/00A61P39/06Y02P20/55
Inventor 黄和张幸乔梦李昺之
Owner NANJING NORMAL UNIVERSITY
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