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Aromatic amido replaced s-triazine compound and preparation and application

The technology of an arylamide group and compound is applied in the field of s-triazine compounds substituted with arylamide group and the preparation field thereof, which can solve the problems of difficult control of reaction conditions, poor yield, complicated steps and the like, and achieves wide industrial application prospect, The effect of easy operation and easy availability of raw materials

Active Publication Date: 2018-11-13
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above methods have disadvantages such as the use of highly toxic reagents, expensive catalysts or ligands, uneasy control of reaction conditions, cumbersome steps, and poor yields, and are subject to certain limitations during use.

Method used

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  • Aromatic amido replaced s-triazine compound and preparation and application
  • Aromatic amido replaced s-triazine compound and preparation and application
  • Aromatic amido replaced s-triazine compound and preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0021] The preparation of embodiment 1 compound (III-1):

[0022] 2-Amino-4-dimethylamino-1,3,5-triazine (121.3mg, 0.87mmol), phenylacetonitrile 5a (200.3mg, 1.71mmol), CuBr (24.8mg, 0.17mmol) in o-di Mix in chlorobenzene (2.0mL), react at 125°C for 15h, after the reaction, add 50mL of water, extract with dichloromethane (20mL×3), combine the organic layers, dry with anhydrous sodium sulfate, filter, Concentrate, column chromatography (eluent is CH 2 Cl 2 : MeOH=30:1, 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 169.2 mg of the target compound (III-1), with a yield of 80%. 1 H NMR (500MHz, CDCl 3 ):δ8.65(s,1H),8.38(s,1H),7.90-7.88(m,2H),7.60-7.56(m,1H),7.51-7.48(m,2H),3.21(s,3H ),3.19(s,3H)

[0023]

Embodiment 2

[0025] Change cuprous chloride to cuprous bromide (10.8mg, 0.07mmol), change the temperature to 135°C, and change the time to 30h. Other operations are the same as in Example 1. The yield is 137.5mg, and the yield is 65%.

Embodiment 3

[0027] Dichlorobenzene was changed to chlorobenzene (9 mL), the temperature was changed to 80° C., other operations were the same as in Example 1, and the yield was 52.9 mg, with a yield of 25%.

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Abstract

The invention provides an aromatic amido replaced s-triazine compound. A 2-amino-1,3,5-triazine compound and a cyanogen compound are mixed and then a solvent is added, reaction is performed under theeffect of a copper catalyst, and reaction liquid posttreatment is performed to obtain the compound. According to the preparation method of the compound, reaction conditions are mild, raw materials areeasy to obtain, operation is convenient, the cost is low, and the compound has a wide industrial application prospect. The aromatic amido replaced s-triazine compound has certain anti-human osteogenic sarcoma cell activity and can be applied to preparation of an antitumor drug, especially to preparation of drugs for treating osteogenic sarcoma. A structural general formula of the compound is shown in the description.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to an aromatic amide group-substituted s-triazine compound, a preparation method and application thereof. Background technique [0002] Triazine compounds have various biological activities such as anticancer, antibacterial, antimalarial, and herbicide. This type of compound is mainly prepared by the reaction of isothiocyanate, guanidine and amidine; or by multi-step reaction of bromobenzene, substituted aniline, diethylamine and cyanuric chloride. The above methods have disadvantages such as the use of highly toxic reagents, expensive catalysts or ligands, difficult control of reaction conditions, cumbersome steps, and poor yields, which are subject to certain limitations in the use process. Therefore, the preparation of novel arylamide-substituted s-triazine compounds has certain application value. Contents of the invention [0003] The present invention provides a new class of triazine ...

Claims

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Application Information

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IPC IPC(8): C07D251/18C07D251/22A61P35/00
CPCA61P35/00C07D251/18C07D251/22
Inventor 张辰刘登辉崔冬梅施宇龙班孟涛郑佳垚
Owner ZHEJIANG UNIV
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