Emodin single-chain diquaternary ammonium salt with anticancer activity and preparation method thereof
A technology of biquaternary ammonium salt and anticancer activity, which is applied in the field of emodin single-chain biquaternary ammonium salt with anticancer activity and its preparation field, can solve the problem that the anticancer activity is not high enough, the direct medicine cannot be achieved, the water solubility is poor, etc. problem, to achieve good application prospects and good anticancer activity.
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Embodiment 1
[0021] Embodiment 1: the synthesis of iodobutyl quaternary ammonium salt
[0022] Take 0.45 mL of methyl bis-octyl tertiary amine or methyl bis-decyl tertiary amine, put it in a 50 mL three-neck flask, add 15 mL of ethylene glycol methyl ether, heat and stir at 100 ° C, slowly add 0.25 mL of 1,4-diiodobutyl alkane, reacted for 12 hours and cooled to room temperature, and the solvent was removed by rotary evaporation, and the obtained solid was subjected to silica gel column chromatography, using dichloromethane-acetone as the eluent, and the volume ratio was 45:1→30:1→15:1→10 :1 for gradient elution to obtain iodobutyl quaternary ammonium salt 1a or 1b , whose characterization data are as follows:
[0023] N-(4-iodobutyl)-N-methyl-N-octyloctane-1-ammonium iodide ( 1a ): reddish-brown solid, yield 75%. 1 H-NMR (400MHz, CDCl 3 )δ: 3.58(t, J =5.6Hz, 2H, C H 2 I), 3.43(t, J =1.6Hz, 2H,N + C H 2 (CH 2 ) 3 I), 3.39(s, 3H, N + C H 3 ), 3.34(t, J =5.6Hz, 4.0H, 2×N +...
Embodiment 2
[0025] Embodiment 2: the synthesis of double protected bromoemodin
[0026] Dissolve 1.6g (5.9mmol) of emodin in 200ml of acetone, add 10g (73mmol) of anhydrous potassium carbonate, slowly add 4ml (43mmol) of dimethyl sulfate under reflux, reflux for 24h, cool to room temperature and spin After removing part of the solvent by evaporation, add 80ml of water and stir for 30min, then filter with suction, wash the filter cake with acetone to obtain 1.34g of bright yellow solid trimethylemodin; dissolve 0.8g (2.56mmol) of trimethylemodin in 60ml of CCl 4 , add 0.20g initiator benzoyl peroxide (BPO) and 1.6g (9.0mmol) brominated reagent N-bromosuccinimide (NBS), reflux reaction in a three-necked flask for 25h, cool to room temperature to get yellow solid, respectively with a small amount of CCl 4 , water and acetone after washing with silica gel column chromatography, using dichloromethane as eluent to separate and obtain 0.83g of yellow solid double-protected bromoemodin, yield 83...
Embodiment 3
[0028] Embodiment 3: the synthesis of double protection emodin tertiary amine
[0029] 100mg (0.26mmol) of double-protected bromoemodin synthesized in Example 2 was dissolved in chloroform, poured into a 50mL three-necked flask, and added 140mg (2.5mmol) KOH, 5mL water, 50mgTEBA (benzyl triethyl chloride Ammonium chloride, as a phase transfer catalyst), and 0.35mL of dimethylamine with a mass concentration of 33% (2.6mmol) in water (2.6mmol), stirred at room temperature for 4h, after the reaction, the solution was extracted 3 times with 15mL of chloroform, the organic layers were combined, and rotary evaporation After removing the solvent, the obtained solid was subjected to silica gel column chromatography, using dichloromethane-acetone as the eluent, according to the volume ratio 45:1→30:1→15:1→10:1→5:1→2:1 Gradient elution to obtain double protected emodin tertiary amine 2 (64.7mg, 0.18mmol), product characterization data are as follows:
[0030] 3-[(Dimethylamino)methyl]...
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