Aromatic glucosamine derivative, its preparation method and antitumor application
A tumor and compound technology, applied in the field of medicine, can solve problems such as difficult tumor treatment
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Embodiment 1
[0050] Embodiment 1: the synthesis of compound II-1
[0051]
[0052] (1) Preparation of 2-chloro-5-nitro-4'-ethoxybenzophenone
[0053] Weigh 2.06g (10mmol) of 2-chloro-5-nitrobenzoic acid and dissolve it in 5mL of thionyl chloride, add 3 drops of pyridine dropwise, then stir and react at 50°C for 3 hours, track by TLC, the reaction of raw materials is complete, stop reaction. The thionyl chloride was removed by rotary evaporation under reduced pressure, and it was directly put into the next reaction without treatment.
[0054] 2.12g (15mmol) of anhydrous AlCl 3 Add to 18mLCH 2 Cl 2 1.35 g (11 mmol) of phenetole was added slowly while keeping the temperature at 0-5° C. After the addition was completed, it was stirred at 0° C. for 15-20 minutes. Then the 2-chloro-5-nitrobenzoyl chloride prepared in the previous step was dissolved in 6mL CH 2 Cl 2 Add it to the phenetole system at a rate that keeps the temperature at 0-5°C, and react for 12 hours to obtain a black-gre...
Embodiment 2
[0061] Embodiment 2: the synthesis of compound II-2
[0062]
[0063] (1) Preparation of compound 3
[0064] Weigh 2.06g (10mmol) of 2-chloro-5-nitrobenzoic acid and dissolve it in 5mL of thionyl chloride, add 3 drops of pyridine dropwise, then stir and react at 50°C for 3 hours, track by TLC, the reaction of raw materials is complete, stop reaction. The thionyl chloride was removed by rotary evaporation under reduced pressure, and it was directly put into the next reaction without treatment.
[0065] 2.12g (15mmol) of anhydrous AlCl 3 Add to 18mLCH 2 Cl 2 1.35 g (11 mmol) of phenetole was added slowly while keeping the temperature at 0-5° C. After the addition was completed, it was stirred at 0° C. for 15-20 minutes. Then the 2-chloro-5-nitrobenzoyl chloride prepared in the previous step was dissolved in 6mL CH 2 Cl 2 Add it to the phenetole system at a rate that keeps the temperature at 0-5°C, and react for 12 hours to obtain a black-green solution. According to T...
Embodiment 3
[0072] Embodiment 3: the synthesis of compound II-3
[0073]
[0074] (1) Preparation of compound 6
[0075] Weigh 4.52g (25mmol) of 2-methyl-5-nitrobenzoic acid and dissolve it in 8mL of thionyl chloride, add 3 drops of pyridine dropwise, then stir and react at 50°C for 3h, track by TLC, the reaction of raw materials is complete, stop reaction. The thionyl chloride was removed by rotary evaporation under reduced pressure, and it was directly put into the next reaction without treatment.
[0076] Anhydrous AlCl 3 5.00g (37.5mmol) was added to 45mLCH 2 Cl 2 3.36 g (27.5 mmol) of phenetole was added slowly while keeping the temperature at 0-5° C. After the addition was completed, it was stirred at 0° C. for 15-20 minutes. Then the 2-methyl-5-nitrobenzoyl chloride prepared in the previous step was dissolved in 14mL CH 2 Cl 2 Add it to the phenetole system at a rate that keeps the temperature at 0-5°C, and react for 1 hour to obtain a black-green solution. According to ...
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