Compound for generating nucleic acid cross-linking action by induction and its preparing method and use

A technology of cross-linking and compounds, which is applied in the direction of active ingredients of hydroxyl compounds, organic chemistry, drug combination, etc., can solve problems such as side effects and no specific recognition of tumor cells, and achieve the effect of simple preparation

Inactive Publication Date: 2007-08-08
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because this kind of antitumor drug has no specific recognition effect on tumor cells and normal cells, it will produce strong unavoidable side effects when used

Method used

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  • Compound for generating nucleic acid cross-linking action by induction and its preparing method and use
  • Compound for generating nucleic acid cross-linking action by induction and its preparing method and use
  • Compound for generating nucleic acid cross-linking action by induction and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 2,6-bis(selenophenylmethylene)phenol (compound 1):

[0030]

[0031]Dissolve 452mg of 2,6-dimethylphenol in 10ml of N,N-dimethylformamide, add 1g of imidazole and 1.12g of tert-butyldimethylsilyl chloride (TBDMSCl) to react overnight at room temperature, and the reaction ends Afterwards, the solvent was evaporated and the product was separated by column chromatography (ethyl acetate:cyclohexane=1:120) to obtain 825 mg of compound 1a. Compound 1a was dissolved in carbon tetrachloride (CCl 4 ), adding 2.5 times the amount of N-bromosuccinimide (NBS), heated to reflux, then added 20 mg of azobisisobutylcyanide, refluxed for 2 hours, evaporated to dryness, and separated by column chromatography product (ethyl acetate:cyclohexane=1:120) to obtain 350 mg of compound 1b.

[0032] Under the protection of nitrogen, first diphenyl diselenide ((PhSe) 2 ) 474mg and sodium borohydride (NaBH 4 ) 114mg dissolved in anhydrous N, N-dimethylformamide (DMF), stirred at...

Embodiment 2

[0035] Synthesis of 4,4'-dihydroxy-3,3'-bis(selenophenylmethylene)biphenyl (compound 2):

[0036]

[0037] 1.86g biphenol was dissolved in 100ml acetone (acetone) and 10ml N,N-dimethylformamide, added 6.9 grams of anhydrous potassium carbonate solid, then added excess methyl iodide (CH 3 1) 5ml of the solution was stirred at room temperature for 8 hours, the reaction solution was extracted with chloroform and water, and the chloroform layer was evaporated to dryness to obtain 1.9g of white solid compound 2a. To 1.9 gram compound 2a and 1.332g paraformaldehyde (CH 2 (2) add 50ml acetic acid, heat to 80°C, then add 5ml 40% mass percent concentration of hydrobromic acid solution, react at 80°C for 3 hours, cool overnight at 4°C, filter the precipitated solid, and use dichloromethane dissolved, washed several times with saturated sodium bicarbonate solution, evaporated to dryness, and separated the product by column chromatography (ethyl acetate:cyclohexane=1:10) to obtain 920...

Embodiment 3

[0039] Synthesis of 1,4-dihydroxy-2,5-bis(selenophenylmethylene)phenol (compound 3):

[0040]

[0041] Under the condition of avoiding light, dissolve 1.1g hydroquinone in 100ml water, add 1.12g potassium hydroxide solid, then add 2.84ml dimethyl sulfate solution, stir at room temperature for 8 hours under nitrogen protection, a large amount of precipitate precipitates, filter and wash with water The solid was repeated several times to obtain 1.045 g of white solid compound 3a. Add 50ml of acetic acid to 1 gram of compound 3a and 1.087g of paraformaldehyde, heat to 60°C, then add 5ml of 40% by mass hydrobromic acid solution, react at 60°C for 4 hours, and cool overnight at 0°C , the precipitated solid was filtered, dissolved in dichloromethane, washed several times with saturated sodium bicarbonate solution, and evaporated to dryness to obtain 1.630 g of compound 3b. Under the protection of nitrogen, first dissolve 1.928 g of diphenyldiselenide and 458 mg of sodium borohyd...

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Abstract

The invention discloses a compound to induce structure to generate crosslinking action of nucleic acid, which comprises the following steps: transmitting phenolic hydroxyl group in the 2, 6-dimethyl phenol, diphenol or hydroquinone into benzyl bromine under alkaline condition; substituting benzyl bromine group into selenium benzene group acted by sodium borohydride and diphenyl sulphone diselenide; stripping protection to obtain compound 1, compound 2 or compound 3.

Description

technical field [0001] The invention relates to a compound capable of inducing nucleic acid cross-linking, a preparation method and application thereof, and belongs to the fields of medicinal chemistry, organic chemistry and biochemistry. Background technique [0002] Cancer is a general term for a group of more than 100 diseases that can affect any part of the body. Its high morbidity and mortality are a long-standing problem for humans and provide great challenges for researchers. Regarding the research on the mechanism of cancer, it is generally believed that the DNA in the cells changes first, leading to its mutation or the activation of oncogenes. Therefore, in the clinical treatment and research of cancer, most of them are anti-tumor drugs that target DNA. This type of drug research can be divided into two categories according to the different forms of action: drugs with covalent bonds and drugs with non-covalent bonds. The former are DNA alkylating agents and cross-li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00A61K31/05A61P35/00
Inventor 周翔翁小成
Owner WUHAN UNIV
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