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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, limited compound structure types, etc., and achieve the effects of simple preparation method, high yield and easy preparation

Inactive Publication Date: 2017-05-31
武汉福山生物医药科技有限公司
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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
[0007] 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

[0037] Embodiment 1: Synthesis of N-phenylselenide benzosuccinimide (compound of formula II)

[0038] Add N-bromobenzosuccinimide (147 mg, 1 mmol), diphenylselenide (312 mg, 1 mmol) and 10 ml of anhydrous acetonitrile into a three-necked flask, heat to 50 °C, and Under argon protection, after stirring for 24 hours, the crude product was obtained by distillation under reduced pressure, and column chromatography (mobile phase: ethyl acetate: petroleum ether = 2:1 (V:V)) gave 260 mg of a yellow powdery solid (compound of formula II) , yield 86%.

[0039] nuclear magnetic resonance 1 H NMR (400 MHz, CDCl 3 ) δ: 7.94-7.92 (2H, dd, J 1 = 5.5 Hz, J 2 = 3.0 Hz), 7.85-7.78(2H, dd, J 1 = 5.5 Hz, J 2 = 3.0 Hz), 7.64-7.60 (2H, m),7.52-7.46(1H, m), 7.32-7.30(2H, m). 13 C NMR: 176.2, 170.3, 140.4, 136.6, 134.5, 129.4, 124.3 123.7.

[0040] ESI-MS: m / z=325.2 (M + Na) + .

Embodiment 2

[0041] Embodiment 2: the synthesis of formula I compound

[0042] Add the compound of formula III (85 mg, 0.66 mmol), the compound of formula II N-phenylselenide substituted benzosuccinimide (200 mg, 0.66 mmol) and anhydrous DMF (10ml) in a three-necked flask, under argon After stirring overnight under protection, the solvent was distilled off under reduced pressure, and column chromatography (mobile phase: methanol: dichloromethane = 1:10) gave 210 mg of a white powder solid (compound of formula I), with a yield of 73%.

[0043] nuclear magnetic resonance 1 H NMR (DMSO) δ: 9.02 (1H, s), 7.84 (2H, s), 7.46-7.35 (2H, m), 7.28-7.13 (3H, m), 7.22 (1H, s), 2.88 (6H, s). 13 C NMR: 175.7, 158.3, 144.2, 130.2, 127.3, 124.9, 37.6.

[0044] ESI-MS: m / z=307.3 (M + Na) + .

[0045] in vitro pharmacology

experiment example 1

[0046] Experimental Example 1: Quinone Reductase Induction Experiment

[0047] Cell culture:

[0048] Mouse hepatoma cell line Hepa 1c1c7 was thawed and cultured at 37 o C, 5% CO 2 in a constant temperature incubator. The culture medium was α-MEM medium containing 10% fetal bovine serum and 1% antibiotics (100 U / mL penicillin, 100 μg / mL streptomycin). Replace the fresh culture medium every 2-3 days, and when the cell adhesion rate reaches above 85%, digest and count with 0.25% trypsin for later use.

[0049] Quinone reductase induction activity assay:

[0050] It has been known in the prior art that two-phase metabolic enzymes are of great significance for preventing the occurrence of tumors. As one of the two-phase metabolic enzymes, quinone reductase is a class of cell protection enzymes with detoxification and free radical scavenging functions. Paraquinone reductase Components with inductive activity are considered to have cancer-preventive effects at the tumor initiat...

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PUM

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Abstract

The invention relates to application of a selenium-containing compound represented in a formula I (shown in the description) in the preparation of chemical prevention agents and treatment agents for cancers. Experiments prove that the compound represented in the formula I is capable of remarkably reducing the expression of quinone reductase, has no obvious cytotoxic effect under a concentration condition (20 mu M) with quinone reductase induction activity and can be taken as an effectively chemical prevention agent and treatment agent for the 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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IPC IPC(8): C07C391/02A61K31/155A61P35/00
CPCC07C391/02
Inventor 贺贤然
Owner 武汉福山生物医药科技有限公司
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