1,4-naphthoquinone derivative as well as synthetic method and medical application thereof

A synthetic method and derivative technology, applied in drug combination, antineoplastic drugs, organic chemistry, etc., to achieve the effect of easy-to-obtain raw materials, simple operation, and strong anti-cancer activity

Inactive Publication Date: 2018-07-27
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The innovation of the present invention lies in the synthesis of a hybrid structure of p-naphthoquinone and tetrazolopyrimidine. This compound has not been reported yet. According to preliminary pharmacological activity measurements, this compound has strong anticancer activity and can be used as Further development of anticancer drugs

Method used

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  • 1,4-naphthoquinone derivative as well as synthetic method and medical application thereof
  • 1,4-naphthoquinone derivative as well as synthetic method and medical application thereof
  • 1,4-naphthoquinone derivative as well as synthetic method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Put 0.40g of 7-methoxy-2-hydroxy-1,4-naphthoquinone, 0.17g of 5-aminotetrazole and 0.60g of paraformaldehyde in a thick-walled pressure-resistant bottle and mix evenly, the temperature is controlled at 150°C After sealing the tube and heating for 7 hours, the reaction mixture was dissolved with 20 mL of ethyl acetate, washed twice with 20 mL of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and purified by column chromatography to obtain bright yellow solid 9-methoxy-1, 0.15 g of 5-hydro-benzo[g]tetrazol[5,1-b]quinazoline-6,11-dione, the yield was 26.5%.

[0018] After testing, molecular formula: C 13 h 9 N 5 o 3 , Molecular weight: 283.07, Appearance: bright yellow solid. Melting point: >300°C. 1 HNMR (400MHz, DMSO-d 6 )δ: 11.71(s, 1H), 7.97(d, 1H, J=8.8Hz), 7.49(d, 1H, J=2.8Hz), 7.41(dd, 1H, J=2.4, 8.4Hz), 5.37( s,2H),3.95(s,3H); 13 C NMR (100MHz, DMSO-d 6 )δ: 180.8, 178.6, 163.8, 149.6, 139.1, 132.5, 128.6, 125.2, 120.9, 111.3,...

Embodiment 2

[0020] Put 0.80g of 7-methoxy-2-hydroxy-1,4-naphthoquinone, 0.34g of 5-aminotetrazole and 1.44g of paraformaldehyde in a thick-walled pressure-resistant bottle and mix evenly, the temperature is controlled at 160°C After sealing the tube and heating for 6 hours, the reaction mixture was dissolved in 40 mL of ethyl acetate, washed twice with 40 mL of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and purified by column chromatography to obtain bright yellow solid 9-methoxy-1, 0.32 g of 5-hydro-benzo[g]tetrazol[5,1-b]quinazoline-6,11-dione, the yield was 28.1%.

Embodiment 3

[0022] Put 4.0g of 7-methoxy-2-hydroxy-1,4-naphthoquinone, 1.7g of 5-aminotetrazole and 9.0g of paraformaldehyde in a thick-walled pressure-resistant bottle and mix evenly, the temperature is controlled at 170°C After sealing the tube and heating for 5 hours, the reaction mixture was dissolved in 200 mL of ethyl acetate, washed twice with 200 mL of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and purified by column chromatography to obtain bright yellow solid 9-methoxy-1, 5-Hydro-benzo[g]tetrazol[5,1-b]quinazoline-6,11-dione 1.70 g, yield 30.1%.

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Abstract

The invention discloses a 1,4-naphthoquinone derivative as well as a synthetic method and a medical application thereof, and belongs to the technical field of synthesis of compounds with anti-cancer activity. The technical scheme is mainly characterized in that the 1,4-naphthoquinone derivative is 9-methoxy-1,5-hydro-benzo[g]tetrazol[5,1-b] quinazolin-6,11-dione, and the structural formula is shown in the description. The invention further specifically discloses the synthetic method of the 1,4-naphthoquinone derivative and the application of the 1,4-naphthoquinone derivative to preparation ofmalignant tumor treating or / and preventing drugs. The 1,4-naphthoquinone derivative has higher anti-cancer activity for hybrid structure of naphthoquinone and tetrazolo-pyrimidine, and the synthetic method of the 1,4-naphthoquinone derivative has the advantages that the method is green, raw materials are easily available, operation is simple and the like.

Description

technical field [0001] The invention belongs to the technical field of synthesis of compounds with anticancer activity, and specifically relates to a 1,4-naphthoquinone derivative, its synthesis method and its medical application. Background technique [0002] In recent years, the morbidity and mortality of cancer have been increasing year by year. In today's society, the main disease that threatens human health and life is malignant tumor. According to research reports, about 6 million people die from cancer every year in the world, and about 10 million people are diagnosed. In my country, more than 1 million people die of cancer every year, and about 1.8 million people are diagnosed. According to WHO statistics, by 2020, the number of new cancer cases worldwide will increase by 5 million. The development and research of new and effective anti-tumor drugs is a major topic and long-term task in the field of biomedical research. [0003] 1,4-Naphthoquinone compounds are a c...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P35/00
CPCC07D487/04
Inventor 张崇
Owner XINXIANG MEDICAL UNIV
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