Synthesis method and application of N-substituted-5-methylene-pyrrole-2-ketone compound
A ketone compound, methylene pyrrole technology, applied in the field of biomolecular conjugate labeling, can solve problems such as protein structure and function changes, and achieve the effects of fast reaction rate, wide application prospect and high selectivity
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Embodiment 1
[0033] A kind of synthetic method of N-substituted-5-methylene-pyrrol-2-one compound, the chemical structural formula of described N-substituted-5-methylene-pyrrol-2-one compound is:
[0034]
[0035] Wherein R is glycinamide;
[0036] The synthesis method is as follows:
[0037]
[0038] Weigh 202 mg (1 mmol, 1 eq) of 2,5-dimethoxy-2,5-dihydrofurfuryl alcohol acetate into a flask, add 4 mL of 0.1 M HCl aqueous solution, and stir at room temperature for 3 h. The reaction system was neutralized to neutral with sodium bicarbonate solid, and 0.4 mL of 500 mM HEPES buffer was added to adjust the pH to 7.5. Add 148mg (2mmol, 2eq) of glycinamide to the resulting mixture, and react at room temperature for 1h. The solvent was removed by rotary evaporation and separated by methanol / dichloromethane (v / v, 1 / 10) column chromatography to obtain 136 mg of a yellow solid with a yield of 90%. Rf = 0.42 (methanol / dichloromethane = 1 / 10, v / v). 1H NMR (400MHz, DMSO) δ7.48(s,1H),7.31(d,...
Embodiment 2
[0060] A kind of synthetic method of N-substituted-5-methylene-pyrrol-2-one compound, the chemical structural formula of described N-substituted-5-methylene-pyrrol-2-one compound is:
[0061]
[0062] Wherein R is propargyl amine;
[0063] The synthesis method is as follows:
[0064]
[0065] Weigh 202 mg (1 mmol, 1 eq) of 2,5-dimethoxy-2,5-dihydrofurfuryl alcohol acetate into a flask, add 4 mL of 0.1 M HCl aqueous solution, and stir at room temperature for 3 h. The reaction system was neutralized to neutral with sodium bicarbonate solid, and 0.4 mL of 500 mM HEPES buffer solution (50 mM, pH 7.5) was added to adjust the pH to weakly alkaline. Add 28 mg (0.5 mmol, 0.5 eq) of propargylamine to the resulting mixture, and react at room temperature for 1 h. The solvent was removed by rotary evaporation and separated by petroleum ether / ethyl acetate (v / v, 4 / 1) column chromatography to obtain 54 mg of a colorless oily liquid (yield 80%). Rf=0.49 (petroleum ether / ethyl acetat...
Embodiment 3
[0069] A kind of synthetic method of N-substituted-5-methylene-pyrrol-2-one compound, the chemical structural formula of described N-substituted-5-methylene-pyrrol-2-one compound is:
[0070]
[0071] Wherein R is the anticancer drug doxorubicin;
[0072] The synthesis method is as follows:
[0073]
[0074] Weigh 202mg (1mmol, 1eq) of 2,5-dimethoxy-2,5-dihydroacetic acid furfuryl alcohol ester into a flask, add 4mL of 0.1M HCl aqueous solution, and stir at room temperature for 3h. The reaction system was neutralized to neutral with sodium bicarbonate solid, and 0.4 mL of 500 mM HEPES buffer was added to adjust the pH to 7.5. To the resulting mixture was added 290 mg (0.5 mmol, 0.5 eq) of adriamycin in DMSO (1 mL) and reacted at room temperature for 1 h. Extracted three times with 5 mL of dichloromethane, dried over anhydrous magnesium sulfate, removed the solvent by rotary evaporation, and separated by methanol / dichloromethane (v / v, 2%) column chromatography to obtain...
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