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Anticancer active molecular skeleton 1,4-enyne compound and its preparation method and application
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A molecular skeleton and anti-cancer activity technology, applied in the field of organic chemical synthesis, can solve the problems of cumbersome post-processing, limited substrate range, and less success, and achieve good anti-cancer activity, wide application range, and inhibition of cell growth.
Active Publication Date: 2022-02-08
NANJING TECH UNIV
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On the other hand, the reaction is also very sensitive to the acidity of the C–H bond of the nucleophile, and under the standard conditions of the Trost-Tsuji reaction, terminal alkynes are rarely used successfully as nucleophiles.
Currently the most effective dehydration coupling method still requires Pd(PPh 3 ) 4 (10mol%), Ti (25mol%), nitrogen-phosphorus ligand (12mol%), but the scope of substrates is still limited, post-processing is tedious, and it is difficult to apply in drug synthesis
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Embodiment 1
[0029] A, under room temperature condition, benzaldehyde (10mmol), methyl acrylate (10mmol) and DABCO (15mmol) are added in the tetrahydrofuran solution successively, stir a week, obtain reaction mixture; Reaction equation is:
[0030]
[0031] B. The solvent was removed from the reaction mixture under reduced pressure, and the residue was purified by silica gel chromatography with petroleum ether and ethyl acetate (PE / EA) to obtain 2-(hydroxyphenylmethyl)-methyl acrylate as a white solid.
Embodiment 2
[0033] (1) In a 10mL Shrek tube, under argon atmosphere, add 2-(hydroxyphenylmethyl)-methyl acrylate (0.5mmol), triisopropylsilylacetylene (0.2mmol), tetrakis (tri Phenylphosphine)palladium (1mol%), calcium bis(trifluoromethylsulfonyl)imide (5mol%) and ammonium hexafluorophosphate (5mol%) were added to N,N-dimethylacetamide (2mL), Stir the reaction at 100°C, the reaction equation is:
[0034]
[0035] (2) After TLC monitors that the reaction is complete, the reaction solution is extracted, and the solvent is removed with a vacuum rotary evaporator, and the product is separated by thin-layer chromatography. The developing agent is sherwood oil / ethyl acetate system, and the product is light yellow oil 2- Benzyl-5-(triisopropylsilyl)pent-4-ynoic acid methyl ester, yield 91%.
Embodiment 3
[0037] (1) In a 10mL Shrek tube, under argon atmosphere, add cinnamyl alcohol (0.2mmol), 4-ethynyl anisole (0.5mmol), tetrakis(triphenylphosphine) palladium (1mol%), bis Calcium (trifluoromethylsulfonyl)imide (5mol%) and tris(dimethylamino)phosphorus (1.2mol%) were added to N,N-dimethylacetamide (2mL), and stirred at 100°C for reaction, The reaction equation is:
[0038]
[0039] (2) After TLC monitors that the reaction is complete, the reaction solution is extracted, and the solvent is removed by a vacuum rotary evaporator, and the product is separated by thin-layer chromatography. ,Such as figure 1 , 2 As shown, the product was determined to be 1-methoxy-4-(5-phenylpent-4-en-1-yn-1-yl)benzene with a yield of 75%.
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Abstract
The invention discloses an anticancer active molecular skeleton 1,4-enyne compound and a preparation method and application thereof. In the present invention, allyl alcohol raw material, terminal alkyne, tetrakis (triphenylphosphine) palladium, bis (trifluoromethylsulfonyl) imide calcium, and additives are sequentially added to the reaction solvent, and in an argon atmosphere, 100 After the catalytic reaction is carried out for 12 to 48 hours at a temperature of ℃ and in a stirring state, the reaction solvent in the reaction solution is removed and purified to obtain an anticancer active molecular skeleton 1,4-enyne compound. The 1,4-enyne compound can be used as a drug for inhibiting human esophageal cancer cells. The amount of palladium catalyst used in the method of the present invention is 1%, the amount of calcium catalyst is 5%, and the amount is very small but can achieve the expected effect; Heterocycle, alkyl; the method of the present invention is suitable for different types of allyl alcohols, and 1,4-enyne compounds can be synthesized on a scale of 10 g; the 1,4-enyne compounds of the present invention have better anticancer activity.
Description
technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to an anticancer active molecular skeleton 1,4-enyne compound and a preparation method and application thereof. Background technique [0002] 1,4-enyne compounds play an important role in organic synthesis, due to their unique chemical, biological, pharmaceutical activity and carbon skeleton, they are important structures in natural products and bioactive compounds, widely used in pharmaceuticals, agriculture Chemistry and Materials Science. For example, (+)-nigellamine A, aeruginosin 98B and rooperol molecules all contain this structure. [0003] Metal-catalyzed allylation of allyl compounds is one of the most important developments in modern synthetic chemistry and has broad applications in the synthesis of natural products. Trost-Tsuji reaction is the most important method to construct this kind of framework. However, allyl alcohol is difficult t...
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