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Selenium-containing compound and use thereof

A technology for compounds and uses, applied in the field of preparing cancer chemopreventive agents and therapeutic agents, which can solve the problems of further improvement of anticancer efficacy, limited structure types of compounds, limited anticancer spectrum, etc.

Active Publication Date: 2018-10-23
SHENZHEN F&S BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[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
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Effect test

preparation example Construction

[0022] The preparation method of the invention is simple, the yield is high, and N-(ethylselenocyanate)-N'-(methylsulfinylbutyl)urea can be easily prepared.

[0023] In another aspect of the present invention, there is provided a pharmaceutical composition comprising a compound of formula I of the present invention or a pharmaceutically acceptable salt thereof, and optionally a pharmaceutically acceptable excipient and / or carrier. In the pharmaceutical composition of the present invention, in addition to the compound of formula I of the present invention or a pharmaceutically acceptable salt thereof, other pharmaceutically active ingredients may also be included. The pharmaceutical compositions of the present invention may be prepared by conventional techniques, such as those described in Remington: The Science and Practice of Pharmacy, 19th Edition, 1995, which is incorporated herein by reference. The compositions may be presented in conventional forms, such as capsules, tabl...

Embodiment 1

[0057] Embodiment 1: Synthesis of 1-selenocyanoethylamine hydrobromide (compound of formula II)

[0058] Add 2-bromoethylamine hydrobromide (1.74g, 8.5 mmol) and 20ml of anhydrous acetonitrile into a three-necked flask, add potassium selenocyanate (1.24g, 8.6 mmol) under nitrogen protection at room temperature, and stir for 24 hours. Remove the solvent by distillation under reduced pressure, add 30ml of dichloromethane to continue the reaction at room temperature for 15-20 minutes, and distill under reduced pressure again to obtain the crude product, column chromatography (mobile phase: ethyl acetate: petroleum ether = 10:1 (V:V)) 1.65 g of a yellow powdery solid (compound II) was obtained, with a yield of 84%.

[0059] nuclear magnetic resonance 1 H NMR (400 MHz, CDCl 3 ) δ: 4.03 (br s, 2H), 3.67 (s, 2H).

[0060] MS [ESI]: Calculated (C 3 h 7 BrN 2 Se) + , 150; found value: 151.

Embodiment 2

[0061] Embodiment 2: the synthesis of N-(ethyl selenocyanine)-N'-(methylsulfinyl butyl)urea (formula I compound)

[0062] Dissolve 1-selenocyanoethylamine hydrobromide (428 mg, 1.86 mmol) in anhydrous dichloromethane, add triethylamine (513 mg, 5.58 mmol), and add sulforaphane (300 g, 1.86 mmol), heated to 50°C and continued to react for 2 hours. The reaction was complete as detected by TCL, the solvent was distilled off under reduced pressure, and purified by column chromatography (mobile phase: ethyl acetate: dichloromethane = 2:1 (V:V)) to obtain 0.54 g of a white powdery solid (compound of formula I), Yield 89%.

[0063] nuclear magnetic resonance 1H NMR (400 MHz, CD 3 OD) δ: 3.88~3.84 (t, 2H), 3.67~3.65 (t,2H), 3.48~3.44 (t, 2H), 2.91~2.83(m, 2H), 2.65 (s, 3H), 1.91~1.87 (m, 4H); 13 CNMR (75 MHz, CD 3 OD) δ: 180.4, 160.5, 57.7, 54.1, 45.2, 38.6, 27.3, 20.6, 20.2.

[0064] MS [ESI]: Calculated value (C 9 h 17 N 3 OS 2 Se) + , 327; Found: 328.

[0065] in vitro...

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Abstract

The invention relates to a selenium-containing compound represented by formula I, and an application of the compound of formula I in the preparation of a chemopreventive and therapeutic agent for cancers. The compound of the formula I can significantly induce the expression of purine reductase, and can be used as the effective chemopreventive and therapeutic agent for cancers.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a selenium-containing compound, a preparation method thereof, and an application thereof in preparing cancer chemopreventive agents and therapeutic agents. Background technique [0002] Cancer is the leading cause of disease and death in the world. At present, the number of cancer deaths in the world exceeds 6 million people every year, and 8 million new cases are diagnosed. This number is still increasing. According to CA: A Cancer Journal for Clinijicians magazine "Cancer Statistics in China, 2015", among the population of 1.3 billion in my country, the number of new cancer cases and deaths in my country in 2015 were 4.292 million cases and 2.814 cases respectively, equivalent to an average of 12,000 cases per day. 7,500 new cancer cases and 7,500 cancer deaths. The occurrence and development of cancer is a multi-stage gradual evolution process. During this evolution proc...

Claims

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Application Information

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IPC IPC(8): C07C395/00A61K31/21A61P35/00
CPCC07C395/00
Inventor 贺贤然李少磊李晓龙
Owner SHENZHEN F&S BIO TECH
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