KRGD peptide-modified carbolino-hexahydropyrazine-1,4-diketones and their preparation method, antithrombotic effect and use
A technology of hexahydropyrazine and antithrombotic drugs, which is applied in the field of biomedicine and can solve the problem of no antithrombotic compounds and the like
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Embodiment 1
[0028] Example 1 Preparation of (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1)
[0029] Put 400ml of water in a 500ml eggplant bottle, and slowly add 0.2ml of concentrated sulfuric acid. Add 5.0 g (24.5 mmol) of L-tryptophan to the obtained dilute sulfuric acid aqueous solution, and ultrasonically shake until the L-tryptophan is completely dissolved. 7.5 ml of 40% formaldehyde solution was added to the solution, and the reaction mixture was stirred at room temperature for 6 hours. The disappearance of L-tryptophan was detected by thin-layer chromatography, and the reaction was terminated. Concentrated ammonia water was slowly added dropwise to the reaction solution, the pH of the reaction mixture was adjusted to 6, and the reaction mixture was allowed to stand for 0.5 hours. Suction filtration under reduced pressure, the obtained precipitate was washed with water, and the filtered colorless solid was spread on a petri dish, and air-dried to obtain 5.14 g (97%) of t...
Embodiment 2
[0030] Example 2 Preparation of (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (2)
[0031] Add 50ml of methanol to a 100ml eggplant bottle, cool to below 0°C with an ice-salt bath, add 6ml (87mmol) SOCl dropwise under stirring 2 10 minutes after the dropwise addition, 5.0 g (23.1 mmol) (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid was added, the ice bath was removed, and the mixture was stirred overnight at room temperature. Stop the reaction after TLC monitors that the raw materials basically disappear, and the water pump depressurizes to extract methanol and excess SOCl 2 , the residue was dissolved in methanol, and the circulating water vacuum pump was used for three times (10ml×3). The residue was added with diethyl ether, and the circulating water was vacuum pumped, and repeated three times (10ml×3). Add 20ml of water and 20ml of ethyl acetate to the residue, and add saturated NaHCO 3 Adjust the pH of the solution to 7-8, separate the layers...
Embodiment 3
[0032] Example 3 Preparation of (3S)-N-[Boc-Asp(OBzl)]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (3)
[0033] Dissolve 1.61g (5mmol) Boc-Asp (OBzl) in 50ml of anhydrous dichloromethane, add 742mg (6mmol) HOBt and 1.42g (6mmol) DCC under ice-cooling, stir for 5-10 minutes and the reaction solution becomes turbid, add 1.15 g (5 mmol) (3S)-methyl 1,2,3,4-tetrahydro-β-carboline-3-carboxylate, the ice bath was removed after 30 minutes. After reacting at room temperature for 12 hours, TLC showed that the starting point disappeared, the reaction was stopped, DCU was filtered off, the filtrate was concentrated to dryness at 30°C under reduced pressure, and the residue was dissolved in ethyl acetate. Then successively washed three times with saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution, 5% aqueous potassium hydrogensulfate solution, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride soluti...
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