Hydroxamic acid derivant, preparation method and antineoplastic application
A technology of compounds and isomers, applied in the treatment of tumor diseases, in the field of hydroxamic acid compounds, which can solve problems such as no anti-tumor activity
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Embodiment 1
[0102] Synthesis of compound 1
[0103]
[0104] (A), take 100mL of anhydrous methanol in a flask, put it into a low-temperature reactor at -10°C and fully cool it, then add 16mL of SOCl 2 (208mmol), the raw material 20g aspartic acid (150mmol) was added to the reactor in batches, stirred at 15-20°C for 25min, immediately poured into 600mL ether, crystals were precipitated, filtered, washed with ether, and dissolved in methanol to obtain crystals, and then add diethyl ether to repeat the above operation to obtain the pure product. The crystals were redissolved to adjust the pH to neutral, and concentrated to obtain compounds 1a-1c as white solids.
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[0106] Product
Embodiment 2
[0108] Synthesis of compounds 2a-2j
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[0110] (D), N 2 Under protection, 6.5mL of anhydrous formic acid (170mmol) and 8.7mL of acetic anhydride (92.5mmol) were added into a round-bottomed flask, sealed and stirred at 50-60°C for 2h, placed in an ice bath, and 12g of compound 1 (85mmol) were added in batches ), adding anhydrous THF, stirring at room temperature for 60 h, adding a large amount of ether after the reaction, and a white solid was precipitated.
[0111] (E), add 2.8g (14.2mmol) compound 1 in the round bottom flask, and add 50mL water, adjust pH with solid NaOAc to be 7. Add 10mL acetic anhydride, heat to reflux for 30min, cool to room temperature, add 25mL acetic anhydride, Stir the reaction at room temperature for 6 hours, spin dry to obtain an oily substance, add 15mL of acetic anhydride, incubate at 95-100°C for 20 minutes, filter, wash the filter residue with ethyl ester, spin the filtrate to remove the solvent, and separate the product by column ch...
Embodiment 3
[0117] Synthesis of compounds 3a-3r
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[0119] (G), 320 mg of benzyloxyhydroxylamine (O-Benzylhydroxylamine, 2 mmol) from which hydrochloride was removed was dissolved in CH 2 Cl 2 , add 200mg 4 Ȧ molecular sieves, add 90mg acetaldehyde (2.0mmol), N 2 Stir overnight at room temperature, filter molecular sieves, and concentrate the filtrate to obtain a yellow oily Schiff base. Dissolve Schiff's base in methanol, add 380mg NaBH 3 CN (6 mmol), adjust the pH value to 3 with concentrated hydrochloric acid, and stir overnight. After the reaction, adjust the pH value to 12, CH 2 Cl 2 After extraction and concentration, the compound 3 was obtained by silica gel column chromatography which had been treated with ammonia water.
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