Selenium-containing compound and use thereof

A compound and application technology, applied in the field of selenium-containing compounds and their preparation, can solve problems such as side effects, limited anti-cancer spectrum, and limited compound structure types, and achieve the effects of simple preparation method, high yield, and easy preparation

Active Publication Date: 2019-01-04
SHENZHEN F&S BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Surgical treatment methods are effective in removing cancer at an early stage, however, the disadvantage is that sometimes organs have to be removed, which causes side effects and has the uncertainty of cancer spreading to other organs
Radiation therapy is good for effectively treating cancers that occur in a specific organ, but has the following disadvantages: it exposes the patient to the risk of other cancers because of the radiation, it cannot prevent cancer cells from spreading to other organs, and the patient suffers a lot during treatment. pain of
[0008] Although the above-mentioned organic selenium compounds have been discovered, the existing organic selenium compounds still have problems such as anti-cancer efficacy to be further improved, limited anti-cancer spectrum, and limited structural types of compounds, which are far from meeting the growing demands of human beings for cancer prevention and treatment. needs

Method used

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  • Selenium-containing compound and use thereof
  • Selenium-containing compound and use thereof
  • Selenium-containing compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of formula II compound

[0044] In a three-neck flask, dissolve riboflavin (1 g, 2.66 mmol) in pyridine (10 mL), add acetic anhydride (1.356 g, 13.3 mmol), stir for 16 hours, and TLC detects that the reaction is complete. The reaction solution was dissolved in 30 mL of water, the aqueous phase was extracted with dichloromethane (10 mL×3), the combined organic phase was washed with saturated brine (20 mL×1), and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude product was purified by column chromatography (ethyl acetate:petroleum ether (v / v)=20:1) to obtain 721 mg of a yellow powdery solid with a yield of 50%.

[0045] nuclear magnetic resonance 1 H NMR (400 MHz, CDCl 3 ) δ:8.60(s, 1H), 8.03(s, 1H), 7.57(s,1H), 5.68~5.66(d, 1H), 6.46~5.39(m,2H), 4.91(s, 1H), 4.45~4.42(m, 1H), 4.27~4.22(m, 1H), 2.57(s, 3H), 2.45(s, 3H), 2.30(s, 3H), 2.22(s, 3H), 2.08(s, 3H), 1.76(s, 4H).

[0...

Embodiment 2

[0047] Embodiment 2: the synthesis of formula III compound

[0048] In a three-hole flask, dissolve compound II (670 mg) in anhydrous DMF (5 mL), add potassium carbonate (204 mg), potassium iodide (20 mg), stir for 30 minutes, and then add tert-butyl bromoacetate (1.68 g), after addition, reaction solution is warming up to 40 DEG C, continues reaction 16 hours. TLC showed that the reaction was complete. After the reaction solution was cooled to room temperature, water (10 mL) was added, the aqueous phase was extracted with ethyl acetate (15 mL×3), and the combined organic phase was washed with saturated brine (20 mL×1). water and sodium sulfate to dry. The solvent was distilled off under reduced pressure, and the obtained crude product was purified by column chromatography (ethyl acetate:petroleum ether=5:1) to obtain a yellow powdery solid (770 mg), with a yield of 95%.

[0049] nuclear magnetic resonance 1 H NMR (400 MHz, CDCl 3 ) δ:8.02(s, 1H), 7.55(s, 1H), 5.66~5.64(d,...

Embodiment 3

[0051] Embodiment 3: the synthesis of formula IV compound

[0052] Compound III (200 mg, 0.3 mmol) and 1 mL of anhydrous dichloromethane were added to a 100 ml three-necked flask, and the mixture was cooled to 0°C under protection of argon, and 0.3 mL of trifluoroacetic acid was added, heated to 50°C and stirred for 5 h. After the reaction is over, pour the reaction solution into ice water, adjust the pH to 5 with saturated sodium bicarbonate solution, add dichloromethane for extraction, collect the organic phase and wash it with saturated brine, then with water, and dry the collected organic phase with anhydrous magnesium sulfate , filtered with suction, dried in vacuo, and evaporated to dryness. Column chromatography (ethyl acetate: ethanol = 1:1 (V:V)) gave 120 mg of a light yellow solid (compound IV), yield: 66%.

[0053] nuclear magnetic resonance 1 H NMR (400 MHz, D 2 O) δ: 7.82 (s,1H), 7.74 (s, 1H), 5.67-5.65(m, 1H), 5.53 (br t, J=6, 1H), 5.49-4.45(m, 1H), 5.10 ( br ...

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Abstract

The invention relates to an application of riboflavin selenium derivative shown in the description in preparing cancer chemopreventive agent. The compound is capable of significantly inducing the expression of quinone reductase and without significant cytotoxic effect under enzyme-induced activity concentration conditions, and can be used as effective cancer chemopreventive and therapeutic agent.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a selenium-containing compound and its preparation method and application. Background technique [0002] Cancer is the leading cause of disease and death worldwide and is expected to continue to increase as modern technologies increase life expectancy. During the life of a cell, small changes to DNA called "mutations" occasionally occur. Of these mutations, some mutations (called "silent mutations") do not result in any substantial change in the function of the cell, while others alter the way the cell functions. Multiple mechanisms prevent mutated cells from continuing the cell cycle, and if the genetic error is not corrected, the cells "suicide" through a process known as "apoptosis." However, if mutations occur in proteins involved in cell cycle regulation, this can lead to uncontrolled cell proliferation (known as tumor formation), which can further develop into cance...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00
CPCC07D487/04
Inventor 贺贤然李少磊
Owner SHENZHEN F&S BIO TECH
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