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Anticancer active molecular skeleton 1,4-enyne compound, and preparation method and application thereof

A technology of molecular skeleton and anti-cancer activity, applied in the field of organic chemical synthesis, can solve the problems of cumbersome post-processing, limited substrate scope, less success, etc., to achieve good anti-cancer activity, wide application range, and cell growth inhibition effect.

Active Publication Date: 2019-05-03
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • Anticancer active molecular skeleton 1,4-enyne compound, and preparation method and application thereof
  • Anticancer active molecular skeleton 1,4-enyne compound, and preparation method and application thereof
  • Anticancer active molecular skeleton 1,4-enyne compound, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A, under room temperature conditions, 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 developer is a 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. ,like 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. The preparation method comprises the following steps: an allyl alcohol raw material, terminal alkyne, tetrakis (triphenylphosphine)palladium, calcium bis(trifluoromethyl sulfonyl)imide and an additive are added into a reaction solvent in sequence; a catalytic reaction is carried out for 12-48 hours at an argon atmosphere at a temperature of 100 DEG C and under a stirring state; a reaction solvent in the reaction solution is removed; and purifying is carried outto obtain the anticancer active molecular skeleton 1,4-enyne compound. The 1,4-enyne compound can be used for medicines inhibiting human esophageal carcinoma cells. The usage amount of a palladium catalyst in the method is 1%, the usage amount of a calcium catalyst is 5%, the usage amounts are extremely small, but an expected effect can be achieved. According to the method disclosed by the invention, the substrate application range is wide, and the allyl alcohol can contain various substituted phenyls, heterocyclic rings and alkyls. The method disclosed by the invention is suitable for different types of allyl alcohol, and the 1,4-enyne compound can be synthesized in a scale of 10 g. The 1,4-enyne compound disclosed by the invention has relatively good anti-cancer 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...

Claims

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Application Information

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IPC IPC(8): C07C41/30C07C43/215C07F7/08A61P35/00
Inventor 解沛忠孙作恋罗德平
Owner NANJING UNIV OF TECH
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