3S-indoleethyl-6S-polar amino acid modified piperazine-2,5-dione, and synthesis, activity and application thereof
An amino, diketone technology, applied in the field of biomedicine, can solve the problems of unsatisfactory clinical efficacy 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) of Boc-Lys(Cbz) in 100mL of anhydrous tetrahydrofuran (THF), and add 2.7g (20mmol) of 1-hydroxybenzotriazole (HOBt) to the suspension in an ice bath. And 5.0g (25mmol) of dicyclohexylcarbodiimide (DCC), and then stirred for 30min. After that, 8.0 g (25 mmol) of Trp-OBzl was added. The reaction compound was added dropwise with N-methylmorpholine (NMM) to adjust the pH to 9. The reaction mixture was first stirred under an ice bath for 1 h, and then 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 resulting ethyl acetate solution was sequentially used with 5% KHSO 4 Wash with aqueous solution 3 times and saturated NaCl aqueous solution 3 times. Anhydrous Na for ethyl acetate layer 2 SO 4 Dry for 12h, filter, and concentrate the filtrate to dryness under re...
Embodiment 2
[0021] Example 2 Preparation of Lys(Cbz)-Trp-OBzl
[0022] 3.8 g (5 mmol) Boc-Lys(Cbz)-Trp-OBzl and 52 mL of hydrogen chloride in ethyl acetate were slowly mixed with stirring in an ice bath. The resulting solution was stirred in an ice bath for 5h. 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 thoroughly with anhydrous ether to obtain 3.45 g (92%) of the title compound as a yellow powder. ESI-MS(m / e):557[M+H] + .
Embodiment 3
[0023] Example 3 Preparation of (3S,6S)-3-(benzyloxycarbonylamino-n-butyl)-6-(indole-3-ethyl)-piperazine-2,5-dione (1)
[0024] 3.45 g (6.2 mmol) Lys(Cbz)-Trp-OBzl was dissolved in 150 mL ethyl acetate. After the obtained solution was washed three times with a 5% aqueous sodium bicarbonate solution, the ethyl acetate solution was stirred at room temperature for 12 hours to allow colorless solids to be analyzed. 1.9 g (55%) of the title compound was filtered off. ESI-MS(m / e):449[M+H] + .
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