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Dimethylamino-substituted [1,2,4]triazolo-s-triazine compounds and their preparation and application

A dimethylamine-based compound technology, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of triazinone derivatives with single structure, few preparation methods, and difficult to obtain raw materials, etc., and achieve a wide range of industrial application prospects , Raw materials are easy to obtain, and the effect of easy operation

Active Publication Date: 2020-09-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are few preparation methods for this type of compound, mainly using amino-substituted [1,2,4]triazole and triethyl orthoformate as raw materials to prepare [1,2,4]triazole and homogeneous Triazine compound, the preparation method steps are loaded down with trivial details, and raw material is difficult to obtain, and the structure of prepared triazone derivative is single, has certain limitation

Method used

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  • Dimethylamino-substituted [1,2,4]triazolo-s-triazine compounds and their preparation and application
  • Dimethylamino-substituted [1,2,4]triazolo-s-triazine compounds and their preparation and application
  • Dimethylamino-substituted [1,2,4]triazolo-s-triazine compounds and their preparation and application

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Embodiment 1

[0020] The preparation of embodiment 1 compound (III-1):

[0021] 2-amino-4-dimethylamino-1,3,5-triazine (150.8mg, 1.1mmol), benzonitrile (555.7mg, 5.4mmol), cuprous chloride (21.3mg, 0.2mmol) and Zinc chloride (14.7mg, 0.1mmol) was mixed with chlorobenzene (3mL) and reacted at 125°C for 20h. After the reaction, add 50mL of water, extract with dichloromethane (20mL×3), and combine the organic layers , dried with anhydrous sodium sulfate, filtered, concentrated, column chromatography (eluent is CH 2 Cl 2 : EtOAc=10:1, V:V), collect R f The eluate with a value of 0.3-0.35 (monitored by TLC, the developing solvent is the same as the eluent), the solvent was distilled off under reduced pressure, and dried to obtain 157.2 mg of the target compound (III-1), with a yield of 61%. 1 H NMR (500MHz, CDCl 3 ): δ8.9409 (s, 1H), 8.28-8.26 (m, 2H), 7.50-7.27 (m, 3H), 3.33 (s, 3H), 3.30 (s, 3H).

[0022]

Embodiment 2

[0024] Cuprous chloride was changed to cuprous bromide (61.8mg, 0.4mmol), and other operations were the same as in Example 1 after 30h, yielding 67.3mg, yield 26%.

Embodiment 3

[0026] The cuprous chloride was changed to cuprous iodide (41.1 mg, 0.2 mmol), and the other operations were the same as in Example 1. The yield was 37.0 mg, and the yield was 14%.

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Abstract

The invention provides a dimethylamino-substituted [1,2,4]triazole-s-triazine compound. A preparation method of the dimethylamino-substituted [1,2,4]triazole-s-triazine compound comprises the following steps: mixing a cyanide compound and 2-amino-4-dimethylamino-1,3,5-triazine, and adding the mixture into a solvent; reacting at the temperature of 60 to 135 DEG C for 15 to 30 hours while stirring in the presence of a copper catalyst and additives; after the reaction is finished, performing posttreatment on the reaction solution to obtain the dimethylamino-substituted [1,2,4]triazole-s-triazinecompound. The preparation method has the advantages of reasonable design, mild technological reaction conditions, ready availability of raw materials, convenience in operation, low cost and wide industrial application prospect. The dimethylamino-substituted [1,2,4]triazole-s-triazine compound provided by the invention shows certain anti-human osteosarcoma cell activity, can be applied to the preparation of an anti-tumor active medicament, especially to the preparation of an osteosarcoma treatment medicament, lays a foundation for the screening and development of new medicaments, and has higherpractical value. The general molecular formula is shown in the description.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a dimethylamino-substituted [1,2,4]triazolo-s-triazine compound and a preparation method and application thereof. Background technique [0002] [1,2,4]Triazolo-s-triazine compounds are a new class of heterocyclic compounds formed by condensing 1,2,4-triazole rings and s-triazine rings. It has a wide range of applications in fields such as science and biology. There are few preparation methods for this type of compound, mainly using amino-substituted [1,2,4]triazole and triethyl orthoformate as raw materials to prepare [1,2,4]triazole and homogeneous Triazine compounds, the preparation method steps are cumbersome, the raw materials are not easy to obtain, and the prepared triazone derivatives have a single structure, which has certain limitations. Therefore, it is of great theoretical and practical significance to develop a new and convenient method for the synthesis of [1,2,4]triazolo-s-t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61P35/00
CPCA61P35/00C07D487/04
Inventor 张辰施宇龙崔冬梅汪涛
Owner ZHEJIANG UNIV