1s-methyl-β-tetrahydrocarbolinyl-k(pak)-rgdv, its synthesis, activity and application
A technology of -arg-gly-asp-val, methyl, applied in 1S-methyl-β-tetrahydrocarboline-K(PAK)-RGDV, its synthesis, activity and application fields, can solve the preparation difficulties , reductive environmental sensitivity, difficulty in preservation, etc.
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Embodiment 1
[0017] Example 1 Preparation of benzyl 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (1)
[0018] 1 mL of concentrated sulfuric acid with a concentration of 98% was added dropwise to 800 mL of distilled water, and after stirring evenly, 10.0 g (34 mmol) of L-Trp-OBzl was added into it three times. Stir for five minutes to thoroughly suspend L-Trp-OBzl and the aqueous sulfuric acid solution. After that, 10 mL of 40% acetaldehyde aqueous solution was added dropwise to the suspension. The reaction mixture was stirred for 12 h, and then 3 mL of concentrated ammonia water was added dropwise to adjust the pH of the reaction solution to 8. The reaction compound was allowed to stand for 1 h until the product was fully separated out. The solid was filtered off and dried to give 9.84 g (90%) of a pale yellow solid as benzyl 1R-methyl-1,2,3,4-tetrahydro-β-carboline-3S-carboxylate and 1S-methyl - Mixture of benzyl 1,2,3,4-tetrahydro-β-carboline-3S-carboxylate. ESI-MS(m / e): 321...
Embodiment 2
[0019] Example 2 Preparation of N-Boc-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (2)
[0020] 9.84g (30.8mmol) of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate benzyl ester obtained in Example 1 was treated with 20mL of N,N-dimethylformamide (DMF) dissolved. Add 6.98 g (32.0 mmol) (Boc) to the solution at 0°C 2 O. The resulting solution was adjusted to pH 12 with triethylamine and stirred at room temperature for 48h. The reaction mixture was concentrated under reduced pressure to remove DMF. The residue was dissolved with 100 mL of ethyl acetate. The obtained ethyl acetate solution was washed with 5% potassium hydrogen sulfate aqueous solution (50 mL×3) and saturated sodium chloride aqueous solution (50 mL×3) successively. The separated ethyl acetate layer was dried over anhydrous sodium sulfate for 12 h, filtered, and the filtrate was concentrated under reduced pressure to obtain an oily substance. The oil was separated on a silica ge...
Embodiment 3
[0021] Example 3 Preparation of Boc-1S-methyl-1,2,3,4-tetrahydro-β-carboline-3S-carboxylic acid (3)
[0022] To the solution of 1.0 g (2.38 mmol) N-Boc-1S-methyl-1,2,3,4-tetrahydro-β-carboline-3S-carboxylic acid benzyl ester and 40 mL of anhydrous tetrahydrofuran was added 100 mg of Pd / C, stir to make a homogeneous suspension. The air in the reaction system was evacuated under reduced pressure, hydrogen was introduced, and stirred at room temperature for 10 h. TLC (dichloromethane / methanol, 40 / 1) showed N-Boc-1S-methyl-1,2,3,4-tetrahydro- The benzyl β-carboline-3S-carboxylate disappeared completely. The Pd / C was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain a colorless powder with ESI-MS (m / e) of 329 [M-H] - .
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