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Selenium-containing compound and use thereof

A compound and application technology, applied in the field of selenium-containing compounds and their preparation, can solve the problems of side effects, limited anti-cancer spectrum, inability to prevent cancer cells from spreading to other organs, and achieve the effect of simple preparation method and high yield

Active Publication Date: 2017-04-19
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

[0040] Example 1: Synthesis of 2',3',4',5'-tetraacetyl-riboflavin (Compound II)

[0041] Add riboflavin (5.0g, 13mmol), 40ml of anhydrous acetic anhydride and 10ml of pyridine in a three-necked flask, heat to 50°C, pass through argon protection, stir for 24 hours, add saturated ammonium chloride solution and ethyl acetate After separation, the aqueous phase was extracted with ethyl acetate (3×60ml), the organic phase was collected, dried over anhydrous magnesium sulfate, filtered with suction, and distilled under reduced pressure to obtain a crude product, which was subjected to column chromatography (mobile phase: ethyl acetate: Petroleum ether = 5:1 (V:V)) to obtain 6.10 g of yellow powdery solid (compound II), with a yield of 86%.

[0042] nuclear magnetic resonance 1 H NMR (400 MHz, CDCl 3 ) δ: 9.11 (br s, 1H), 7.93 (s, 1H),7.52 (s, 1H), 5.59 (br d, J = 9 Hz, 1H), 5.41- 5.39 (m, 1H), 5.34-5.31 (m,1H), 4.85 (br s, 2H), 4.36 (dd, J 1 =12Hz; J 2 =3 Hz, 1H), 4.18(dd, ...

Embodiment 2

[0044] Example 2: Synthesis of 2',3',4',5'-tetraacetyl-N(3)-tert-butoxyacetyl riboflavin (compound III)

[0045] Add 5ml of anhydrous DMF to a three-necked flask, sequentially add compound II (544 mg, 1.0 mmol), potassium carbonate (166 mg, 1.2 mmol), catalytic amount of potassium iodide, stir for 30 min under the protection of argon, and then slowly dropwise add dissolved 2 - tert-butyl bromoacetate (1 mL, 6.9 mmol) in anhydrous DMF 10 mL, heated to 40° C. and protected from light for 20 h. After the reaction is complete, extract with dichloromethane (3×20ml), collect the organic phase, wash with saturated sodium bicarbonate (10mL), water (10mL), saturated brine (10mL) successively, add anhydrous magnesium sulfate to the organic phase and dry , Suction filtration and distillation under reduced pressure to obtain crude product, column chromatography (mobile phase: ethyl acetate: dichloromethane = 1:1 (V:V)) to obtain 0.52 g of yellow powdery solid (compound III), yield 79% . ...

Embodiment 3

[0048] Example 3: Synthesis of 2',3',4',5'-tetraacetyl-N(3)-riboflavin acetic acid (Compound IV)

[0049] Add compound III (200 mg, 0.3 mmol) and 1 ml of anhydrous dichloromethane into a 100 ml three-neck flask, pass through argon to protect and cool to 0 °C, add 0.3 ml of trifluoroacetic acid, heat up to 50 °C and stir 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%.

[0050] nuclear magnetic resonance 1 H NMR (400 MHz, D 2 O) δ: 7.88 (s, 1H), 7.77 (s, 1H), 5.69-5.64(m, 1H), 5.54 (t, J = 6 Hz, 1H), 5.51-4.47(m, 1H), 5...

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Abstract

The invention relates to an application of a selenium-containing compound represented by formula I in the preparation of chemical prevention agents and treatment agents of cancers. Experiments confirm that the compound of the formula I can substantially induce the quinone reductase expression, have unobvious cytotoxicity under a quinone reductase induction active concentration condition (20 [mu]M), and can be used as an effective chemical prevention agent or treatment agent of cancers.

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): C07D475/14A61K31/525A61K31/095A61P35/00
CPCC07D475/14
Inventor 贺贤然
Owner SHENZHEN F&S BIO TECH
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