3R-indole-methyl-6R-polar amino acid-modified piperazine-2,5-dione and synthesis, activity and application thereof
A technology of n-hexanoylamino and amino, applied in the field of biomedicine, can solve the problems of unsatisfactory clinical curative effect of tumor chemotherapy and no anti-tumor metastasis effect
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Embodiment 1
[0019] Example 1 Preparation of Boc-Lys(Cbz)-Trp-OBzl
[0020] Suspend 7.7g (20mmol) Boc-Lys (Cbz) in 100mL of anhydrous tetrahydrofuran (THF), and add 2.7g (20mmol) 1-hydroxybenzotriazole (HOBt) to the suspension successively under ice-cooling And 5.0g (25mmol) dicyclohexylcarbodiimide (DCC), then stirred for 30min. Afterwards, 8.0 g (25 mmol) Trp-OBzl was added. The reaction compound was added dropwise to N-methylmorpholine (NMM) to adjust the pH to 9. The reaction mixture was first stirred under ice bath for 1 h, and then stirred at room temperature for 12 h. The reaction compound was filtered, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 150 mL of ethyl acetate solution. The obtained ethyl acetate solution was sequentially washed with 5% KHSO 4 Wash 3 times with aqueous solution and 3 times with saturated NaCl aqueous solution. Ethyl acetate layer with anhydrous Na 2 SO 4 Dry for 12h, filter, and concentrate the filtrate to ...
Embodiment 2
[0021] Example 2 Preparation of Lys(Cbz)-Trp-OBzl
[0022] 3.8 g (5 mmol) Boc-Lys(Cbz)-Trp-OBzl was slowly mixed with 52 mL of hydrogen chloride in ethyl acetate (4M) under ice bath and stirring. The resulting solution was stirred for 5 h in an ice bath. After that, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 50 mL of anhydrous ethyl acetate, and the resulting solution was concentrated under reduced pressure. This operation was repeated three times. The residue was washed well with anhydrous ether to obtain 3.41 g (93%) of the title compound as a yellow powder. ESI-MS(m / e):557[M+H] + .
Embodiment 3
[0023] Example 3 Preparation of (3R,6R)-3-(benzyloxycarbonylamino-n-butyl)-6-(indole-3-methyl)-piperazine-2,5-dione (1)
[0024] 3.45 g (6.2 mmol) of Lys(Cbz)-Trp-OBzl were dissolved in 150 mL of ethyl acetate. After the obtained solution was washed three times with 5% aqueous sodium bicarbonate solution, the ethyl acetate solution was stirred at room temperature for 12 h to fully separate out the colorless solid. 1.8 g (51%) of the title compound were filtered off. ESI-MS(m / e):449[M+H] + .
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