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Heterozygote of adjacent naphthoquinone and tetrazol-pyrimidine and synthetic method thereof

A technology of tetrazolium and aminotetrazolium, which is applied in the field of hybrids and achieves the effects of easy availability of raw materials, high yield and simple operation

Inactive Publication Date: 2015-04-22
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The innovation of the present invention is to use the method of molecular hybridization to synthesize a hybrid containing o-naphthoquinone and tetrazolopyrimidine. This compound has not been reported yet. After preliminary pharmacological activity determination, this compound has a strong anti-inflammatory effect. cancer activity

Method used

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  • Heterozygote of adjacent naphthoquinone and tetrazol-pyrimidine and synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Put 0.85g of 5-aminotetrazole, 0.6g of paraformaldehyde, 1.74g of 2-hydroxy-1,4-naphthoquinone and 0.15g of p-toluenesulfonic acid together in a 25ml reaction flask and mix well, heat and stir, the temperature Controlled at 120°C, reacted for 1 hour. The reaction mixture was dissolved in 25 ml of dichloromethane, washed twice with 25 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with ethanol to obtain the corresponding yellow product 4,6-dihydro-benzo[ h ]tetrazolium[5,1- b ] Quinazoline-7,8-dione 1.92 g, productive rate is 76%.

[0020] After testing, molecular formula: C 12 h 7 N 5 o 2 , Molecular weight: 253.06, Appearance: Yellow solid, Melting point: >400℃;

[0021] IR (KBr): v 1672, 1656, 1589, 1573, 1308, 1072, 949, 720 cm -1 ;

[0022] 1 H NMR (400 MHz, DMSO- d 6 ) δ : 11.79 (s, 1H), 8.05 (dd, 1H, , J = 7.2, 17.6 Hz) , 7.93-7.84 (m, 2H), 5.39 (s, 2H);

[0023] 13 C NMR (100 MHz, DMSO- d...

Embodiment 2

[0026] Put 4.25g of 5-aminotetrazole, 3.3g of paraformaldehyde, 8.7g of 2-hydroxy-1,4-naphthoquinone and 0.75g of p-toluenesulfonic acid together in a 100ml reaction flask and mix well, heat and stir, the temperature Controlled at 125°C, after 2 hours of reaction. The reaction mixture was dissolved in 150 ml of dichloromethane, washed twice with 150 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with ethanol to obtain the corresponding yellow product 4,6-dihydro-benzo[ h ]tetrazolium[5,1- b ] Quinazoline-7,8-dione 10.21 g, productive rate is 81%.

Embodiment 3

[0028] Put 8.5g of 5-aminotetrazole, 7.5g of paraformaldehyde, 17.4g of 2-hydroxy-1,4-naphthoquinone and 1.5g of p-toluenesulfonic acid together in a 250ml reaction flask and mix evenly, heat and stir, the temperature Controlled at 130°C, reacted for 3 hours. The reaction mixture was dissolved in 300 ml of dichloromethane, washed twice with 300 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with ethanol to obtain the corresponding yellow product 4,6-dihydro-benzo[ h ]tetrazolium[5,1- b ] Quinazoline-7,8-dione 18.98 g, productive rate is 74%.

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Abstract

The invention provides a 4,6-dihydro-benzo [h] tetrazole [5,1-b] quinazoline-7,8-diketone and a synthetic method of the 4,6-dihydro-benzo [h] tetrazole [5,1-b] quinazoline-7,8-diketone. The method comprises the steps that 5-amino-1H-tetrazole, paraformaldehyde, 2-hydroxyl-1, 4- naphthoquinone and toluene sulfonic acid at a catalyst amount are evenly mixed, heated and stirred, the temperature of the mixture is controlled to be in the range of 120-130 DEG C, and the reaction time is 1-3 hours. The 4, 6-dihydro-benzo [h] tetrazole [5, 1-b] quinazoline-7, 8-diketone is a heterozygote of adjacent naphthoquinone and tetrazol [1, 5-a] pyrimidine and is high in antitumor activity. The synthetic method has the advantages that the environment-friendly effect is achieved, raw materials are easy to obtain, operations are simple, and the yield is high.

Description

technical field [0001] The present invention relates to a hybrid of o-naphthoquinone and tetrazolopyrimidine, in particular to a 4,6-dihydro-benzo[ h ]tetrazolium[5,1- b ] quinazoline-7,8-dione. Background technique [0002] In recent years, cancer has become the disease with the highest fatality rate in human beings. 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] O-naphthoquinones are a class of chemical components that exist widely in nature, and have various biological activities such as antibacterial, antiviral, antitumor, and antioxidative. Representative compounds containing o-naphthoquinone structure include β-lapachone, Mansonone E, dihydrotanshinone, tanshinone IIA, and salwycin, etc. In recent years, o-naphthoquinones have attracted widespread attention due to their unique anticancer activity. Natural o-naphthoquinones and their synthetic analogues have novel st...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P35/00
CPCC07D487/04
Inventor 武利强杨晓娟
Owner XINXIANG MEDICAL UNIV
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