Glucosamine modified RGD oligopeptides derivative, preparation method and application thereof
An amino acid and amino acid-based technology, applied in the direction of peptides, tetrapeptide components, drug combinations, etc., can solve the problems of small adverse reactions and obvious side effects
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preparation example 1
[0072] Preparation Example 1 Arg(NO 2 ) preparation
[0073] In an ice-salt bath, concentrated nitric acid (6 mL) and concentrated sulfuric acid (6 mL) were added to a 100 ml eggplant bottle, and arginine (Arg) (3.55 g, 20.38 mmol) was added in batches to the above mixture, and the reaction was carried out for about 2 h. Add ice water (7mL) dropwise to the reaction mixture, slowly adjust the pH to 8 with concentrated ammonia water, then adjust the pH to 6 with acetic acid, a large amount of white solid precipitates, filter, and mix dichloromethane and methanol at 80°C The solvent recrystallized the colorless solid to give the title compound (2.98 g, 13.60 mmol) as a colorless solid. Yield 67%.
preparation example 2Bo
[0074] Preparation example 2Boc-Arg (NO 2 ) preparation
[0075] Add R(NO 2 ) (2.18g, 9.95mmol), then add water (20mL), adjust the pH to 9 with 2N NaOH under ice cooling, the mixture is still white and turbid. Di-tert-butyl dicarbonate (Boc 2 O) (2.48g, 11.38mmol), reacted at room temperature, adjusted the pH of the reaction mixture to 9, the mixed solution gradually became clear, TLC (thin layer chromatography) monitored the reaction was complete for about 48h. The reaction solution was concentrated to dryness under reduced pressure, a small amount of water (50 mL) was added to the residue, and the pH was adjusted to 2 with saturated potassium bisulfate, extracted with ethyl acetate (40 mL×3), and the organic layer was washed with saturated sodium chloride (20 mL× 3), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain the target compound (2.53 g, 7.90 mmol) as a colorless solid with a yield of 79%. ...
preparation example 3To
[0076] Preparation Example 3 Preparation of Tos Gly-OBzl
[0077] Add glycine (Gly) (3.75g, 50.00mmol), benzyl alcohol (60mL, 600mmol), p-toluenesulfonic acid (11.40g, 60mmol) and cyclohexane (60mL) into a 250ml eggplant bottle. The reaction was carried out at 100°C in an oil bath, and the reaction was completed in about 60 hours as monitored by TLC. The reactant was cooled to room temperature, a large amount of diethyl ether (150 mL) was added, and the target compound (16.5 g, 49.0 mmol) was obtained by filtration as a colorless solid. Yield 98%.
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