Synthetic method of triphenyl-n-(colchicine amido)butylphosphonium chloride compound and application of the compound in antitumor medicine
A technology of narciscine amide and triphenyl chloride, which is applied in the field of synthesis of triphenyl-n-butylphosphonium chloride, can solve the problems of high toxicity of colchicine, animal death, and limited application, and achieve Improving the efficiency of drug action, overcoming excessive toxicity, and reducing the effect of dosage
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Embodiment 1
[0041] A kind of synthetic method of triphenyl chloride-4-(colchicine amido) butylphosphonium compound of the present embodiment comprises the steps:
[0042] (1) Synthesis of N-Boc colchicine
[0043] Dissolve 1.04g (2.6mmol) colchicine in 15ml of dichloromethane solution after dry distillation, then add 0.35g (2.91mmol) 4-dimethylaminopyridine, 0.42ml (2.91mmol) to the three-necked flask successively triethylamine. Stir and reflux and slowly dropwise add 3.20 g (14.66 mmol) of Boc anhydride to the solution, react for 6 h, and monitor the progress of the reaction by TLC. After the reaction was complete, the solvent was distilled off under reduced pressure and separated by column chromatography to obtain 0.93 g of a light yellow solid with a yield of 68.72%. m.p.: 87.3—89.6°C. IR(KBr)cm -1 :3653.34,2974.62,2934.58,2836.21,1737.32,1679.84,1618.21,1588.59,1488.51,1460.13,1435.05,1407.35,1370.32,1324.04,1283.67,1252.04,1141.28,1092.32,1021.12,1001.58,982.51,923.07,846.03,774....
Embodiment 2
[0053] A kind of synthetic method of triphenyl chloride-3-(colchicine amido) butylphosphonium compound of the present embodiment is basically the same as Example 1, the difference is only in:
[0054] (1) the chloroalkyl chloride that the present embodiment adopts is 3-chlorobutyryl chloride;
[0055] (2) The process of step (4) and step (5) is different:
[0056] (4) Synthesis of N-3-chlorobutyryl deacetylcolchicine
[0057] Take 0.50 g of deacetylcolchicine prepared in step (3), dissolve 0.15 ml of triethylamine in 10 ml of chloroform, stir in an ice-water bath, and add 0.15 ml of 3-chlorobutyryl chloride dropwise into the solution. After reacting for 2 hours, remove the ice-water bath and heat to condense to reflux, and react for 1.5 hours. The progress of the reaction was monitored by TLC. After the reaction was complete, the pH was adjusted to neutral with triethylamine, and the solvent was distilled off under reduced pressure. Column chromatography separated to obtai...
Embodiment 3
[0061] A kind of synthetic method of triphenyl chloride-2-(colchicine amido) butylphosphonium compound of the present embodiment is basically the same as Example 1, the difference is only in:
[0062] (1) the chloroalkyl chloride that present embodiment adopts is 2-chlorobutyryl chloride;
[0063] (2) The process of step (4) and step (5) is different:
[0064] (4) Synthesis of N-2-chlorobutyryl deacetylcolchicine
[0065] Take 0.50 g of deacetylcolchicine prepared in step (3), dissolve 0.125 ml of triethylamine in 10 ml of chloroform, stir in an ice-water bath, and add 0.125 ml of 2-chlorobutyryl chloride dropwise into the solution. After reacting for 2 hours, remove the ice-water bath, heat and condense to reflux, and react for 2 hours. The progress of the reaction was monitored by TLC. After the reaction was complete, the pH was adjusted to neutral with triethylamine, and the solvent was distilled off under reduced pressure. Separated by column chromatography, 0.38 g of ...
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