Thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside as well as preparation method and application of thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside

A technology of thioglycosidic bond stanol glycosides and thioglycosidic bond sterol glycosides is applied in the directions of metabolic diseases, steroids, antitoxic agents, etc., and can solve the problems of lack of access means, short drug half-life, and uneven structure, etc. Achieving the effect of simplifying experimental protocols, achieving productivity, and increasing flexibility

Active Publication Date: 2020-12-18
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 thioglycosid...

Method used

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  • Thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside as well as preparation method and application of thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside
  • Thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside as well as preparation method and application of thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside
  • Thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside as well as preparation method and application of thioglycosidic bond sterol glucoside and thioglycosidic bond stanol glucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Using brassicasterol (compound 1) as the raw material and fully acetyl-protected glucose (compound 5) as the glycosyl donor

[0047] Synthesis of compound 2

[0048] Natural sterol crude compound 1 (brassicasterol, 0.7g, 1.68mmol) was dissolved in anhydrous DCM (10mL) and anhydrous pyridine (0.24mL) pre-cooled to 0°C, and then trifluoromethanesulfonic anhydride ( 1.422g (2.8mmol) of anhydrous DCM (3.5mL) solution was slowly added dropwise to the solution of the above compound 1, the time for the addition was more than 30 minutes, and when adding DCM, it was necessary to ensure that the system was at 0°C, and the reaction was completed after the addition The system needs to continue to react at 0°C for 1 hour. After the reaction, wash with saturated sodium bicarbonate solution (50 mL), wash with magnesium sulfate (MgSO 4 ), filtered and concentrated by evaporation to obtain compound 2 (0.752g, 83%) substituted by trifluoromethanesulfonyl at the C-3 position, 1H NMR (30...

Embodiment 2

[0058] Using campestanol (compound 1) as raw material, perbenzoyl-protected glucose (compound 5) as glycosyl donor

[0059] Synthesis of compound 2

[0060] Crude natural stanol Compound 1 (0.7 g, 1.68 mmol) was dissolved in anhydrous DCM (10 mL) and anhydrous pyridine (0.24 mL) pre-cooled to 0 °C, followed by trifluoromethanesulfonic anhydride (1.422 g 2.8 mmol) of anhydrous DCM (3.5mL) solution was slowly added dropwise to the solution of Compound 1, the time for the addition was more than 30min, and when DCM was added, it was necessary to ensure that the system was at 0°C. After the addition, the reaction system needed to be at 0 The reaction was continued for 1 hour at °C. After the reaction, wash with saturated sodium bicarbonate solution (50mL), wash with magnesium sulfate (MgSO 4 ) was dried, filtered and concentrated by evaporation to obtain compound 2 (0.730g, 81%) substituted by trifluoromethanesulfonyl at the C-3 position, 1H NMR (300MHz, DMSO) δ1.24 (m, 3H), 1.90...

Embodiment 3

[0070] The preparation method of embodiment 3 is the same as that of embodiment 1, and the difference is that compound 1 is campesterol, and the consumption of trifluoromethanesulfonic anhydride in step (1) is 1 times of the molar number of compound 1; Reaction is at -10 ℃ Carry out; the consumption of potassium thioacetate in step (2) is 1 times of compound 2 moles; Reaction is carried out at-20 ℃; Reaction solvent used in step (3) is ethyl acetate; Reagent used is potassium hydroxide , the basic reagent consumption is 5 times of compound 3 moles; Reaction solvent used in step (4) is toluene, and used Lewis acid catalyst is trifluoromethanesulfonic acid, and the consumption of Lewis acid catalyst is 0.5 times of compound 3 moles; The inert protective gas is helium; in the step (5), the compound 6 is hydrolyzed and deprotected with a base, the base is potassium hydroxide (KOH), the reaction solvent used is ether, and the amount of the alkaline reagent is 0.5 times the mole numb...

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Abstract

The invention discloses thioglycosidic bond sterol glycoside and thioglycosidic bond stanol glycoside as well as a preparation method and application thereof, the structures of the thioglycosidic bondsterol glycoside or thioglycosidic bond stanol glycoside are respectively shown as a formula I and a formula II, and R1 in the formula I and the formula II represents a carbon chain formed by 8-10 carbon atoms. According to the method, substitution of trifluoromethanesulfonic anhydride on the C3th site of sterol/stanol is developed and optimized, sulfydryl substitution of the C3th site is achieved, glycosylation of the C3th site is achieved through fully-protected glucose, finally, a protecting group can be removed under the alkaline condition, and thioglycosidic bond sterol/stanol glucosideis obtained. The whole 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 theglycosylated product.

Description

technical field [0001] The invention belongs to glycosylated sterols / stanols, in particular to thioglucoside-bonded sterol glycosides and thioglucoside-bonded stanol glycosides and their preparation methods and applications. Background technique [0002] Phytosterols, also known as phytosterols, are steroidal compounds with plant active ingredients. They consist of three six-membered rings and one five-membered ring. There is a hydroxyl group at the C-3 position, and 8-10 side chains of carbon atoms. Those with a double bond at the C-5 position are called sterols, and those with a saturated C-5 position are called stanols. Common phytosterols include campesterol, sitosterol, stigmasterol, and brassicasterol, and common phytostanols include campestanol and sitostanol , stigmastanol, brassicastanol. Phytosterols / stanols have the functions of inhibiting cholesterol absorption, anti-inflammation, antipyretic, anti-oxidation, prevention and treatment of cardiovascular diseases...

Claims

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Application Information

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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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