Benzopyrone skeleton derivative, preparation method and uses thereof

A technology of benzopyrone and derivatives, which is applied in the field of chemical pharmacy, can solve the problems of reducing bile discharge, toxicity, and poor selectivity, and achieve the effects of increasing sensitivity, reversing drug resistance, and simple structure

Active Publication Date: 2019-06-21
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AI-Extracted Technical Summary

Problems solved by technology

[0004] According to the specificity, affinity and toxicity of P-gp inhibitors, they are divided into three generations: first-generation inhibitors are represented by verapamil and cyclosporin A, calcium ion antagonists and immunosuppressants and other drugs, due to their There is obvious toxicity within the effective dose for reversing drug resistance, which limits its clinical application; the second-generation inhibitors are mainly analogues of the first generation and some compounds with new structures, such as the oxidation product of cyclosporine A, valsip Although valspodar exhibits good pharmacokinetic properties, due to problems such as inhibition of CYP3A4, reduction of bile excretion, and poor selectivity, the pharmacokin...
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The invention belongs to the field of chemical pharmacy, and relates to a benzopyrone skeleton derivative, a preparation method and uses thereof, particularly to a derivative with a 2-ethyl benzopyrone bicyclic mother nucleus containing 7-alkoxy and 8-aromatic acid or an aromatic hydrocarbon acid methanol ester substituted derivative. According to the present invention, the experiment results showthat the derivative is almost non-toxic to normal cells and drug-resistant tumor cells, can significantly reverse the drug-resistant activity of P-gp overexpressing A2780/T and KB-V to drugs by combining with paclitaxel and vincristine, does not improve the drug sensitivity of P-gp-dependent drug-resistant tumor cells, and can establish the foundation in the obtaining of the sensitizer capable ofrestoring the drug sensitivity of MDR tumors caused by P-gp overexpression and the overcoming of tumor MDR caused by P-gp overexpression.

Application Domain

Organic chemistryAntineoplastic agents

Technology Topic

PaclitaxelNormal cell +12


  • Benzopyrone skeleton derivative, preparation method and uses thereof
  • Benzopyrone skeleton derivative, preparation method and uses thereof
  • Benzopyrone skeleton derivative, preparation method and uses thereof


  • Experimental program(7)

Example Embodiment

[0038] Example 1
[0039] Synthesis of compound 1-(2-hydroxy-4-methoxymethoxy)-phenyl-1,3-pentanedione (1) in general formula one
[0040] In a three-necked flask, 60% sodium hydride (8.86g, 221.5mmol), anhydrous tetrahydrofuran (62.4mL), 2-hydroxy-4-methoxymethoxy-acetophenone (13.28) dissolved in tetrahydrofuran (55.8mL) were added. g, 67.69 mmol), ethyl propionate (104.5 mL, 135.37 mmol). Reflux the reaction for 2h, cool to room temperature, adjust the pH to neutral with hydrochloric acid, evaporate most of the tetrahydrofuran, add ice water, extract with dichloromethane several times, combine the organic phases, wash once with water, wash once with saturated sodium chloride solution, anhydrous Dry with sodium sulfate. After concentration and drying, the crude compound 1 (16.22 g) was obtained, with a crude yield of 95.0%, which was a pale yellow solid, which can be directly used for the next reaction without purification.

Example Embodiment

[0041] Example 2
[0042] Synthesis of compound 2-ethyl-7-hydroxy-4H-chromen-4-one (2) in general formula one
[0043] Compound 1 (16.22g, 64.31mmol) was dissolved in ethanol (500mL), concentrated hydrochloric acid (10mL) was added, and the reaction was refluxed for 0.5h. After evaporation of ethanol and drying, the crude product 2 can be obtained. The yield is 100% and can be carried out directly without purification. Next reaction.

Example Embodiment

[0044] Example 3
[0045] Synthesis of the compound 2-ethyl-7-hydroxy-8-carbaldehyde-4H-chromen-4-one (3) in general formula one
[0046] Compound 2 (30.0g, 157.7mmol) was dissolved in glacial acetic acid (500mL), added urotropine (154.78g, 1.10mol), heated to 90~100℃ and reacted for 3h, evaporated part of glacial acetic acid; added 5N hydrochloric acid (800mL) ), reflux and continue the reaction for 0.5h, pour a small stream of the reaction liquid into ice water (1000mL), precipitate a yellow solid, filter, wash with ice water several times until there is no pungent odor, and obtain yellow solid compound 3 (8.65g) after drying , The yield is 25.13%.


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Description & Claims & Application Information

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