Acetyl amino acid acyl derivatives of betulin and its preparation method
A technology of acetyl amino acid and amino acid acyl, which is applied in the field of acetyl amino acid acyl derivatives of betulin and its preparation, can solve the problems of low price and poor anti-tumor activity, and achieve the effect of simple synthesis method and enhanced anti-tumor activity
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Embodiment 1
[0039] Example 1 Preparation of Derivative YWZ-001
[0040]
[0041] Add 1 mmol acetylglycine, 1.2 mmol 1-hydroxybenzotriazole (HOBT), 0.1 mmol 4-dimethylaminopyridine (DMAP) and 3 mmol N-ethyldiisopropylamine (DIPEA) to 5 Milliliter N,N-dimethylacetamide (DMAC) was magnetically stirred, and then continued to add 1 mmol 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC .HCl), under the protection of nitrogen, the carboxyl group was activated for 1 hour at 25°C.
[0042] Then, 1.0 mmol of betulin was added thereto and reacted at 25° C. for 12 hours. After the reaction, the reaction liquid was dropped into 250 ml of distilled water drop by drop, and a precipitate was precipitated out; the precipitated solution was suction filtered to obtain a solid, and then the solid was dried in a blast drying oven at 60°C and then subjected to silica gel column chromatography (petroleum ether: ethyl acetate=2:1 volume ratio), 0.35 g of white betulin acetamino acid acyl der...
Embodiment 2
[0045] Example 2 Preparation of Derivative YWZ-002
[0046]
[0047]1 mmol acetylalanine, 2 mmol 1-hydroxybenzotriazole (HOBT), 0.2 mmol 4-dimethylaminopyridine (DMAP) and 2 mmol) N-ethyldiisopropylamine (DIPEA) Add to 8 ml of N,N-dimethylacetamide (DMAC) and stir magnetically, then continue to add 1.5 mmol of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Salt (EDC.HCl), under the protection of nitrogen, the carboxyl group was activated at 20°C for 1.5 hours.
[0048] Then, 1.1 mmol of betulin was added thereto and reacted at 20° C. for 10 hours. After the reaction, the reaction solution was dropped into 280 ml of distilled water drop by drop, and a precipitate was precipitated; the precipitated solution was suction filtered to obtain a solid, and then the solid was dried in a blast drying oven at 40°C and then subjected to silica gel column chromatography (Petroleum ether:ethyl acetate=5:1 volume ratio), the white betulin acetamino acid acyl derivative YWZ-...
Embodiment 3
[0051] Example 3 Preparation of Derivative YWZ-003
[0052]
[0053] Add 1 mmol acetylvaline, 2 mmol 1-hydroxybenzotriazole (HOBT), 0.3 mmol 4-dimethylaminopyridine (DMAP) and 2.5 mmol N-ethyldiisopropylamine (DIPEA) Add 2 millimoles of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to 4 milliliters of N,N-dimethylacetamide (DMAC) with magnetic stirring (EDC.HCl), under the protection of nitrogen, the carboxyl group was activated at 40°C for 4 hours.
[0054] Then, 1.00 mmol of betulin was added thereto and reacted at 40° C. for 24 hours. After the reaction, the reaction solution was dropped into 240 ml of distilled water drop by drop, and a precipitate was precipitated; the precipitated solution was suction filtered to obtain a solid, and then the solid was dried in a blast drying oven at 60°C and then subjected to silica gel column chromatography (Petroleum ether:ethyl acetate=1:2 volume ratio), the white betulin acetamino acid acyl derivative YWZ-3 was obt...
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