Isoliquiritigenin derivant with antineoplastic activity and synthetic method thereof
An anti-tumor activity, isoliquiritigenin technology, applied in anti-tumor drugs, drug combinations, chemical instruments and methods, etc., can solve problems such as affecting a wide range of applications, difficult isoliquiritigenin, and reducing anti-tumor activity.
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Embodiment 1
[0017] The preparation of 3'-dimethylaminomethyl-2',4,4'-trihydroxychalcone, the structural formula is as follows:
[0018]
[0019] Weigh 0.64 g of isoliquiritigenin and put it into a round bottom flask, and add 0.46 mL of a 33% dimethylamine aqueous solution with a mass fraction. The temperature is controlled at 20°C. During electromagnetic stirring, 0.23mL of formaldehyde solution with a mass fraction of 36% and 6mL of glacial acetic acid are rapidly added dropwise, and the reaction is stopped immediately after the addition is completed. Add a small amount of water to dilute and extract with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, separated on a silica gel column, and eluted with ethyl acetate to remove unreacted isoliquiritigenin, and then eluted with ethyl acetate-methanol solution with a volume ratio of 4:1. The liquid was concentrated to dryness to obtain a yellow solid. Recrystallization with a mixed solvent of petrole...
Embodiment 2
[0025] The preparation of 3'-morpholinomethyl-2',4,4'-trihydroxychalcone, the structural formula is as follows:
[0026]
[0027] Weigh 0.64g of isoliquiritigenin into a round bottom flask, add 0.26mL of morpholine, and control the temperature at 20°C. During electromagnetic stirring, quickly drop 0.23mL of formaldehyde solution with a mass fraction of 36% and 6mL of glacial acetic acid, dropwise Immediately stop the reaction. Add a small amount of water to dilute and extract with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, separated on a silica gel column, and eluted with ethyl acetate to remove unreacted isoliquiritigenin, and then eluted with ethyl acetate-methanol solution with a volume ratio of 4:1. The liquid was concentrated to dryness to obtain a yellow solid. Recrystallization with a mixed solvent of petroleum ether and acetone at a volume ratio of 1:1.5 gave 0.36 g of a yellow powder with a yield of 40.4%.
[0028] mp...
Embodiment 3
[0033] The preparation of 3'-cyclohexylaminomethyl-2',4,4'-trihydroxychalcone, the structural formula is as follows:
[0034]
[0035] Weigh 0.64g of isoliquiritigenin and put it into a round bottom flask, add 0.35mL of cyclohexylamine, control the temperature at 20°C, during the electromagnetic stirring process, quickly drop 0.23mL of 36% formaldehyde solution and 6mL of glacial acetic acid, drop The reaction was stopped immediately after the addition was completed. Add a small amount of water to dilute and extract with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, separated on a silica gel column, and eluted with ethyl acetate to remove unreacted isoliquiritigenin, and then eluted with ethyl acetate-methanol solution with a volume ratio of 4:1. The liquid was concentrated to dryness to obtain a yellow solid. Recrystallization with a mixed solvent of petroleum ether and acetone with a volume ratio of 1:2 gave 0.40 g of a yellow pow...
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