7-(4-chlorphenyl)-5,6-dihydro-7ah-benzo[h]1,2,4-triazolo[3,4-b]quinazoline-5,6-diketone and synthetic method thereof

A technology of chlorophenyl and triazole, applied in the field of 1,2-naphthoquinone derivatives

Inactive Publication Date: 2013-02-06
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 chlorine-substituted nitrogen-heterocyclic 1,2-naphthoquinone compound, which has not yet been reported

Method used

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Examples

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Embodiment Construction

[0015] The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention.

[0016] Put 0.84g 3-amino-1,2,4-triazole, 1.40g 4-chlorobenzaldehyde, 1.74g 2-hydroxy-1,4-naphthoquinone and 0.2g p-toluenesulfonic acid together in 50ml reaction Mix well in the bottle, heat and stir, the temperature is controlled at 110°C, and react for 2.5 hours. The reaction mixture was dissolved in 20 ml of dichloromethane, washed twice with 20 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the yellow corresponding product 7-(4-chlorophenyl)-5 ,6-dihydro-7a H -Benzo[ h ][1,2,4]-Triazolo[3,4- b ] Quinazoline-5,6-dione 3.17g, productive rate is 88%.

[0017] After testing, molecular formula: C 19 h 9 ClN 4 o 2 , Molecular weight: 360.04, Appearance: Yellow solid, Melting point: 245-246°C;

[0018] IR (KBr) ν : 3074, 2923, 1684, 1598, 1586, 15...

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Abstract

The invention provides 7-(4-chlorphenyl)-5,6-dihydro-7aH-benzo[h]1,2,4-triazolo[3,4-b]quinazoline-5,6-diketone and a synthetic method thereof. The method comprises the following steps of: uniformly mixing 3-amino-1,2,4-triazole, p-chlorobenzaldehyde, 2-hydroxyl-1,4-naphthaquinone and p-methylbenzene sulfonic acid with a usage amount of catalyst, heating and stirring, controlling the temperature at 110-125 DEG C and reacting for 2.5-3 hours. The 7-(4-chlorphenyl)5,6-dihydro-7aH-benzo[h]1,2,4-triazolo[3,4-b]quinazoline-5,6-diketone prepared according to the invention introduces chlorine atoms, thus having stronger activity and being more beneficial to absorption. The method provided by the invention is green and environment-friendly, and has the characteristics that the raw materials are available, the operation is simple and the yield is high.

Description

technical field [0001] The present invention relates to a 1,2-naphthoquinone derivative, in particular to a 7-(4-chlorophenyl)-5,6-dihydro-7a H -Benzo[ h ][1,2,4]-Triazolo[3,4- b ] quinazoline-5,6-dione. Background technique [0002] Cancer is a kind of disease that seriously threatens human health. Finding effective anticancer drugs is an important research topic in the world medical field. According to literature reports, 1,2-Naphthoquinone derivatives have anti-tumor, anti-inflammatory, antibacterial and other properties. biological activity. In recent years, the antitumor activity of 1,2-naphthoquinone derivatives has attracted increasing attention. Some natural 1,2-naphthoquinone compounds such as: β - Lappaquinone, Rhinacanthone, Biflorin, Mansongone E and synthetic 1,2-naphthoquinone compounds such as: salvexin have shown unique anti-tumor effects. Compared with 1,4-naphthoquinones, the antitumor effect of 1,2-naphthoquinones has the following three advantages; 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P35/00
Inventor 武利强黄艳芹杨晓娟律海霞李慧智
Owner XINXIANG MEDICAL UNIV
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