Organometallic drug gemcitabine-ferrocene and preparation method thereof
A gemcitabine and organometallic technology, applied in the field of organometallic medicine gemcitabine-ferrocene and its preparation, can solve the problems of high price, limited application, poor water solubility and the like, and achieve the effects of low price, simple preparation method and simple preparation process
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[0025] The preparation method steps are as follows:
[0026] Step 1: Under the condition of ice bath, add gemcitabine and triethylamine into a dry single-necked flask according to the molar ratio of 1:5.0~6.0, use dichloromethane as solvent, stir and react for 5~10min, and the molar ratio of gemcitabine to 1 : 2.5 to 3.5 bromoisobutyryl bromide is dissolved in dichloromethane and added dropwise to the reaction system. After the dropwise addition, react for 30 to 40 minutes, then react at 20 to 30°C for 12 to 14 hours; after the reaction, use Saturated sodium bicarbonate solution extraction, the organic phase is concentrated by rotary evaporation, the filtrate is passed through a silica gel column, the filtrate is taken, and the light yellow solid obtained after evaporating the solvent to dryness with a rotary evaporator is the tribromoguicibine prodrug;
[0027] Step 2: Add tribromoguicibine prodrug, sodium azide, and cesium chloride into a dry single-necked flask according to...
Embodiment 1
[0031] 1. Under ice-bath conditions, add 50 mg of gemcitabine to a 100 ml dry single-necked flask, add 10 ml of dichloromethane to dissolve, then add 125 μl of triethylamine and keep stirring. Measure 100 μl of bromoisobutyryl bromide and dissolve it in 10 ml of dichloromethane, slowly drop it into the ice-bath reaction system, stir for 30 minutes after the dropwise addition, transfer to room temperature and stir, and react for 12 hours. After the reaction, extract twice with saturated sodium bicarbonate solution, remove the lower organic phase, concentrate the liquid by rotary evaporation, pass through a silica gel column, take the filtrate, and evaporate the solvent to dryness with a rotary evaporator to obtain 133 mg of white tribromogemcitabine solid.
[0032] 2. Add 133mg of tribromogemcitabine, 52mg of sodium azide and 135mg of cesium chloride into a dry 100ml single-necked flask, add 15ml of N,N-dimethylformamide as a solvent, heat and stir at 60°C, Reaction 12h. After...
Embodiment 2
[0036] 1. Under ice-bath conditions, add 100 mg of gemcitabine to a 100 ml dry single-necked flask, add 20 ml of dichloromethane to dissolve, then add 250 μl of triethylamine and keep stirring. Measure 200 μl of bromoisobutyryl bromide and dissolve it in 10ml of dichloromethane, slowly drop it into the ice-bath reaction system, stir for 30 minutes after the dropwise addition, transfer to room temperature and stir, and react for 12 hours. After the reaction, extract twice with saturated sodium bicarbonate solution, remove the lower organic phase, concentrate the liquid by rotary evaporation, pass through a silica gel column, take the filtrate, and evaporate the solvent to dryness with a rotary evaporator to obtain 280 mg of white tribromogemcitabine solid.
[0037] 2. Add 280 mg of tribromogemcitabine, 110 mg of sodium azide and 265 mg of cesium chloride into a dry 100 ml single-necked flask, add 15 ml of N,N-dimethylformamide as a solvent, and heat and stir at 60 ° C. Reaction...
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