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A class of polyene diketone antitumor compounds

A technology of polyene dione and antitumor drug, applied in the field of polyene dione compounds, can solve the problems of fast metabolism of curcumin, unsatisfactory bioavailability, low absorption efficiency and the like

Inactive Publication Date: 2019-08-30
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although curcumin has the potential to be an ideal antitumor drug, its application value is limited by its fast metabolism, low absorption, poor anticancer activity and unsatisfactory bioavailability in the body.
Sardjiman et al [S.S.Sardjiman, M.S.Reksohadiprodjo, L.Hakim, H.Van der Goot, H.Timmerman, 1,5-Diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidant agents.Synthesis and structure-activity relationship, Eur.J.Med.Chem.32(1997)625-630.] found that the active methylene and β-diketone structure of curcumin is the cause of its instability in physiological environment, fast metabolism and low absorption efficiency The main reason

Method used

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  • A class of polyene diketone antitumor compounds
  • A class of polyene diketone antitumor compounds
  • A class of polyene diketone antitumor compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The in vitro free radical scavenging test of embodiment 1 target compound

[0036] Accurately weigh 19.7mg of DPPH, dissolve it with 450mL of absolute ethanol ultrasonically and dilute it to a 500mL volumetric flask to prepare a 0.1mM DPPH solution, and store it in the refrigerator in the dark for future use.

[0037] The configuration and experimental operation of the sample to be tested are as follows: Weigh 10.0 mg of the sample to be tested, add absolute ethanol to make a 10 mg / L mother solution, and the corresponding molar concentration is about 16-20 μmol / L. Use a pipette gun to accurately measure 100 μL of the sample to be tested and 200 μL of absolute ethanol in the microplate plate, set the background on the microplate reader for zero adjustment, to eliminate the influence of the sample on the test results; pipette 100 μL of distilled water and 200 μL of The 0.1mM DPPH solution was used as the blank control group; 100 μL of the test solution and 200 μL of the D...

Embodiment 2

[0040] Antitumor activity test of embodiment 2 target compound

[0041] Culture medium preparation: 89% culture medium + 10% fetal bovine serum + 1% double antibody.

[0042] PBS preparation: accurately weigh 3.61g Na 2 HPO 4 12H 2 O, 0.2g KCl, 0.8g NaCl and 0.2g KH 2 PO 4 , add 800mL double distilled water to dissolve completely, then dilute to 1000mL with double distilled water. Pack in glass bottles for autoclaving and store in a 4°C refrigerator for later use.

[0043] Preparation of MTT mother liquor: Accurately weigh 250mg MTT, dissolve in 50mL PBS in the dark, shake gently in a water bath at 60°C to dissolve completely, filter through a 0.22μm microporous filter membrane, and dispense at -20°C Store in dark place.

[0044] Drug preparation: Accurately weigh 9 target compounds according to the dosing concentration of the MTT experiment in Table 3, add 200uL DMSO to dissolve completely, and store in a refrigerator at 4°C in the dark.

[0045] Table 3 Dosing concen...

Embodiment 3

[0053] The preparation of embodiment 3 target object

[0054] At 0° C., in a mixed system of 1 mL of acetone and 2 mL of NaOH (15%) aqueous solution, slowly dropwise add an ethanol solution (5 mL) of substituted benzaldehyde (2 mmol), and react at room temperature after the addition is complete. After the reaction of raw materials was detected by TLC, the solvent was removed by rotary evaporation, dichloromethane was added to completely dissolve the solid crude product in the bottle, and then the pH was adjusted to neutral with saturated ammonium chloride solution, washed with saturated brine and dried with anhydrous magnesium sulfate. After separation by column chromatography (petroleum ether / ethyl acetate=10 / 1, V / V), the substituted methyl styrene acetone was obtained in the form of white powder or white oil, with a yield of 75-89%. Then, under the protection of nitrogen, dry and ground KOH (0.44g, 0.08mmol) was added to the obtained mixed solution of substituted methyl styr...

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Abstract

The invention provides a class of new polyene diketone compounds, wherein the new polyene diketone compounds have good free radical scavenging and antitumor activities, can be used for preparing antitumor drugs for treating humans or animals, has characteristics of low preparation cost and good achievability, and has a molecular structure formula defined in the specification.

Description

technical field [0001] The invention relates to a class of polyenedione compounds, and also relates to the synthesis of the compounds and their application in the preparation of antitumor drugs. Background technique [0002] Cancer is a major disease that seriously threatens human life and health. There are more than 14 million new cancer cases in the world every year. In my country, there are 4.29 million new cases each year, accounting for 20% of the global new cases, and 2.81 million deaths. In 2013, the overall cancer incidence rate in my country was 270.59 / 100,000. By 2020, It is estimated that the compound growth rate of the number of cancer patients in my country can reach 24.35%. In 2013, it was reported that about 7.9 million people died of cancer worldwide, including about 1.3 million deaths from lung cancer, 803,000 deaths from gastric cancer, 639,000 deaths from colorectal cancer, 610,000 deaths from liver cancer, and 519,000 deaths from breast cancer. Today, ab...

Claims

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Application Information

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IPC IPC(8): C07C49/255C07C49/248A61P35/00C07C45/74
CPCA61P35/00C07C49/248C07C49/255
Inventor 吴凯群钟山刘媛
Owner SICHUAN UNIV
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