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Selenium cyanide compound and application thereof

A compound, haloacyl halide technology, applied in the field of selenocyanide and its preparation, can solve the problems of inability to prevent cancer cells from spreading to other organs, limited anti-cancer spectrum, and further improvement of anti-tumor efficacy

Inactive Publication Date: 2019-07-12
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-tumor efficacy to be further improved, limited anti-cancer spectrum, and limited compound structure types, which are far from meeting the growing human needs for tumor prevention and treatment. need

Method used

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  • Selenium cyanide compound and application thereof
  • Selenium cyanide compound and application thereof
  • Selenium cyanide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0024] In the preparation method of the present invention, sodium bicarbonate is preferably used as a catalyst in step (i).

[0025] An exemplary reaction scheme is as follows:

[0026]

[0027] The preparation method of the invention is simple, the yield is high, and the compound of formula I can be easily prepared.

[0028] The present invention also provides the use of a compound of formula I or a pharmaceutically acceptable salt thereof in the preparation of a medicament for preventing and / or treating tumors; preferably, the tumors are selected from colon cancer, breast cancer, prostate cancer, cervical cancer, Gastric cancer, liver cancer, lung cancer and leukemia; particularly preferably, the tumor is selected from gastric cancer, lung cancer, liver cancer and leukemia.

[0029] In another aspect, the present invention provides a pharmaceutical composition comprising a compound of formula I or a pharmaceutically acceptable salt thereof, and optionally pharmaceuticall...

specific Embodiment approach

[0030] The present invention provides the compound described in following formula I

[0031]

[0032] or a pharmaceutically acceptable salt thereof,

[0033] wherein R is a linear or branched alkyl group of 1 to 6 carbon atoms or hydrogen. Preferably, R is a linear or branched alkyl group of 1 to 4 carbon atoms or hydrogen; more preferably, R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, iso Butyl, tert-butyl and hydrogen; in a particularly preferred embodiment, R is selected from methyl, ethyl, n-propyl, isopropyl and hydrogen; in a particularly preferred embodiment, R is selected from methyl radical, ethyl and hydrogen; in a more preferred embodiment, R is selected from methyl and hydrogen.

[0034] The pharmaceutical composition of the present invention comprises the compound of formula I of the present invention or a pharmaceutically acceptable salt thereof, and optional pharmaceutically acceptable excipients and / or carriers. In the pharmaceutical com...

preparation Embodiment 1

[0053] Preparation Example 1: Synthesis of Compound I-a

[0054] The reaction formula is as follows:

[0055]

[0056] In a three-necked flask, paclitaxel (200 mg, 0.23 mmol) was dissolved in a mixed solvent of dichloromethane and water (CH 2 Cl 2 (V): H 2 O(V)=1:1), sodium bicarbonate (42mg, 0.2mmol) was added, bromoacetyl bromide (56mg, 0.28mmol) was added at room temperature, stirred for 1 hour, TLC detected that the reaction was complete. The reaction solution was washed twice with 1N HCl (35ml), and 1% NaHCO 3 (35ml) Na after washing twice 2 SO 3 dry. After the solvent was evaporated to dryness, the solid was dissolved by heating with EtOAc and crystallized on standing. Filtration gave a light brown solid, compound II (191 mg, 71% yield). Dissolve directly in anhydrous acetonitrile, add potassium selenocyanate 145 (33 mg, 0.23 mmol) in batches, and stir at room temperature for 16 hours. After the reaction solution was concentrated, it was dropped into 150ml of...

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Abstract

The invention provides a selenium cyanide compound and an application thereof to prevention or treatment of cancer. The selenium cyanide compound has a structure shown in the formula I. The inventionfurther provides a preparation method of the compound with the structure of the formula I and pharmaceutical composition containing the compound with the structure of the formula I.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a selenocyanide 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 cancer. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/14A61K31/337A61P35/00A61P35/02
CPCC07D305/14
Inventor 贺贤然李少磊
Owner SHENZHEN F&S BIO TECH
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