Triazole derivatives capable of affecting calcium ion channels of tumor cells, preparation method and application thereof

A calcium ion channel, tumor cell technology, applied in the field of triazole derivatives and their preparation, can solve the problems of patients being susceptible to various tumors, reducing human immunity, etc., and achieve significant application value, improve yield, and improve response. Yield effect

Active Publication Date: 2022-04-29
JINAN ASIA PHARMA TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because HIV will reduce the body's immunity, which in turn will cause patients to be prone to various tumors, and the current research on dolutegravir is mainly in the anti-HIV aspect, and it has not been found that it can be applied to treat other diseases

Method used

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  • Triazole derivatives capable of affecting calcium ion channels of tumor cells, preparation method and application thereof
  • Triazole derivatives capable of affecting calcium ion channels of tumor cells, preparation method and application thereof
  • Triazole derivatives capable of affecting calcium ion channels of tumor cells, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076]

[0077] Under the protection of nitrogen and the reaction temperature at 15-25°C, add 30 g of methyl 4-methoxyacetoacetate into 100 mL of tetrahydrofuran, add 24 g of N,N-dimethylformamide dimethyl acetal dropwise, After the addition, keep the temperature at room temperature, stir the reaction for 1 h, then raise the temperature to 35°C, and concentrate to obtain (Z)-2-((2,2-methylamino)methylene)-4-methoxy- Methyl 3-oxobutanoate 37g, LC-MS: 202[M+H] + .

Embodiment 2

[0079]

[0080] Add 20g of (Z)-2-((2,2-methylamino)methylene)-4-methoxy-3-oxobutanoic acid methyl ester to 250mL of anhydrous methanol, at room temperature and nitrogen protection Stir under low temperature until completely dissolved; add 48g of dimethyl oxalate, then cool down to 10°C, add 12g of sodium methoxide, heat up to reflux, cool down to 0°C after the reaction of the raw materials is complete, add dropwise 2N hydrochloric acid to adjust the pH value of the reaction solution to 5-6 , then concentrated in vacuo, then added 150 mL of ethyl acetate to the concentrate, separated the organic phase and then concentrated it into 200 mL of anhydrous methanol, then added 11 g of aminoacetaldehyde dimethyl acetal, stirred for 2.5 hours, cooled to 5°C, added Anhydrous lithium hydroxide 7.2g, control the reaction between 0-5°C; after 30 minutes of reaction, TLC shows that the raw materials have reacted completely, keep the reaction temperature at 0-5°C, add dilute sulfuric acid ...

Embodiment 3

[0082]

[0083] Add 20g of (Z)-2-((2,2-methylamino)methylene)-4-methoxy-3-oxobutanoic acid methyl ester to 250mL of anhydrous methanol, at room temperature and nitrogen protection Stir under low temperature until completely dissolved; add 48g of dimethyl oxalate, then cool down to 10°C, add 15g of sodium ethoxide, heat up to reflux, cool down to 0°C after the reaction of the raw materials is complete, add 2N hydrochloric acid dropwise to adjust the pH value to 5-6, and then Concentrate in vacuo, then add 150 mL of ethyl acetate to the concentrate, separate the organic phase and concentrate, add to 200 mL of anhydrous methanol, then add 11 g of aminoacetaldehyde dimethyl acetal, stir for 2.5 hours, cool to 5 ° C, add anhydrous Lithium hydroxide 7.2g, control the reaction at 0-5°C; after reacting for 30 minutes, keep the reaction temperature at 0-5°C, add 2N hydrochloric acid solution dropwise to adjust the pH value to 1-2, add 100mL of dichloromethane, and separate the organi...

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PUM

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Abstract

The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a triazole derivative capable of affecting calcium ion channels of tumor cells, a preparation method and application thereof. The present invention uses dolutegravir as a lead compound, utilizes the principle of drug splicing, and through a click reaction, changes the benzyl group in the dolutegravir structure into a 1,2,3-triazole structure to obtain a new compound, It can inhibit the growth of tumor cells by affecting calcium ion channels in tumor cells, and has significant application value.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a triazole derivative capable of affecting calcium ion channels of tumor cells, a preparation method and application thereof. Background technique [0002] Dolutegravir is a safe and efficient HIV integrase inhibitor with high genetic barrier and good pharmacokinetic properties. It was developed by GlaxoSmithKline in the United States and approved by the Food and Drug Administration FDA in 2013 listed. Dolutegravir blocks the strand transfer step of retroviral deoxyribonucleic acid (DNA) integration by binding to the integrase active site. The drug is only taken once a day. For the treatment of patients with HIV-1 infection for the first time, the efficacy is equivalent to that of Raltegravir taken twice a day, and it has high safety and strong anti-drug resistance properties. Dolutegravir Wei, as an FDA priority review drug, is expected to reach US$2....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/14A61P35/00
CPCC07D498/14A61P35/00C07B2200/07
Inventor 孙秀伟刘晓斐姚小军王文君王育伟
Owner JINAN ASIA PHARMA TECH
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