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Asymmetrically substituted 1, 3, 5-triazine compound as well as preparation method and application thereof

A technology of ester compounds and compounds, which is applied in the field of biocatalytic synthesis, can solve the problems of low yield, unfriendly environment, and toxic catalysts, and achieve the effects of high yield, reduced catalyst consumption, and broad market prospects

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

AI Technical Summary

Problems solved by technology

[0005] Therefore, one of the objectives of the embodiments of the present invention is to provide an asymmetrically substituted 1,3,5-triazine compound to solve the existing asymmetrically substituted 1,3,5-triazine compounds proposed in the background art above. Most of the compounds are prepared using toxic catalysts, which are not environmentally friendly and have low yields

Method used

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  • Asymmetrically substituted 1, 3, 5-triazine compound as well as preparation method and application thereof
  • Asymmetrically substituted 1, 3, 5-triazine compound as well as preparation method and application thereof
  • Asymmetrically substituted 1, 3, 5-triazine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] A specific synthetic route of an asymmetrically substituted 1,3,5-triazine compound is:

[0087]

[0088] Its concrete synthetic steps are as follows:

[0089] Add 13.5 mg of phenylisothiocyanate and 11.5 mg of tetramethylguanidine to 1 mL of dimethyl sulfoxide, then add 15.6 mg of benzamidine hydrochloride and rabbit hemoglobin (0.5 mol), and slowly add three times the amount tert-butyl hydroperoxide and reacted at 25°C (normal temperature) for ten minutes, and then detected the reaction progress by thin-layer chromatography; then added water to quench the reaction, extracted with ethyl acetate and added anhydrous sodium sulfate to dry , concentrated, followed by further purification by silica gel column chromatography (ethyl acetate / hexane) to obtain N 2 ,N 2 -Dimethyl-N 4 ,6-diphenyl-2,4-diamino-1,3,5-triazine 26.5 mg, yield 91%, white solid.

[0090] In this embodiment, the product is subjected to nuclear magnetic detection and analysis. For specific nuclear ...

Embodiment 2

[0093] A specific synthetic route of an asymmetrically substituted 1,3,5-triazine compound is:

[0094]

[0095] Its concrete synthetic steps are as follows:

[0096] Add 14.9 mg of 4-methylphenyl isothiocyanate and 11.5 mg of tetramethylguanidine into 1 mL of dimethyl sulfoxide, then add 15.6 mg of benzamidine hydrochloride and rabbit hemoglobin (0.5 mol), slowly drop After adding three times the amount of tert-butyl hydroperoxide, react at 25°C (normal temperature) for ten minutes, and then use thin-layer chromatography to detect the reaction progress; then add water to quench the reaction, extract with ethyl acetate and add anhydrous After drying over sodium sulfate, concentration, followed by further purification by silica gel column chromatography (ethyl acetate / hexane) to obtain N 2 ,N 2 -Dimethyl-N 4 -(p-Tolyl)-6-phenyl-2,4-diamino-1,3,5-triazine 27.5 mg, yield 90%, white solid.

[0097] In this example, the product is subjected to nuclear magnetic detection and an...

Embodiment 3

[0100] A specific synthetic route of an asymmetrically substituted 1,3,5-triazine compound is:

[0101]

[0102] Its concrete synthetic steps are as follows:

[0103] Add 14.9 mg of 3-methylphenyl isothiocyanate and 11.5 mg of tetramethylguanidine into 1 mL of dimethyl sulfoxide, then add 15.6 mg of benzamidine hydrochloride and rabbit hemoglobin (0.5 mol), slowly drop After adding three times the amount of tert-butyl hydroperoxide, react at 25°C (normal temperature) for ten minutes, and then use thin-layer chromatography to detect the reaction progress; then add water to quench the reaction, extract with ethyl acetate and add anhydrous After drying over sodium sulfate, concentration, followed by further purification by silica gel column chromatography (ethyl acetate / hexane) to obtain N 2 ,N 2 -Dimethyl-N 4 -(m-Tolyl)-6-phenyl-2,4-diamino-1,3,5-triazine 26.8mg, yield 88%, white solid.

[0104] In this example, the product is subjected to nuclear magnetic detection and a...

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Abstract

The invention relates to the technical field of biocatalytic synthesis, and particularly discloses an asymmetrically substituted 1, 3, 5-triazine compound as well as a preparation method and application thereof. The asymmetrically substituted 1, 3, 5-triazine compound comprises the following raw materials: an isothiocyanate compound, an amidine compound and tetramethylguanidine. According to the asymmetrically substituted 1, 3, 5-triazine compound, heme, horse radish peroxidase, hemoglobin or cytochrome C is adopted as a catalyst, so that the asymmetrically substituted 1, 3, 5-triazine compound is green, non-toxic, environmentally friendly and high in yield, and the problem that most of existing asymmetrically substituted 1, 3, 5-triazine compounds adopt toxic catalysts in preparation, arenot environmentally friendly and are low in yield is solved; and the preparation method provided by the invention is superior to the traditional chemical synthesis method, has the advantages of highefficiency, greenness, short reaction time, mild reaction conditions and no difficult-to-treat metal ion catalysis, and lowers the catalyst consumption.

Description

technical field [0001] The invention relates to the technical field of biocatalytic synthesis, in particular to an asymmetrically substituted 1,3,5-triazine compound and its preparation method and application. Background technique [0002] With the continuous development of science and technology, more and more raw materials are used in biological, chemical, pharmaceutical and other industries. Among them, the core skeleton of 1,3,5-triazine compounds is a very important molecular skeleton, which has a wide range of biological and pharmacological activities, such as anticancer, antiviral, antifungal, antimalarial, anti-inflammatory and Anti-angiogenic activity, 1,3,5-triazines and their surrogates are critical for the generation and escalation of their activity. Therefore, the synthesis of asymmetric 1,3,5-triazine compounds with different bioactive substitutes is of great significance to the research of life science, organic chemistry and medicinal chemistry. [0003] At ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/18A61K31/53A61P35/00A61P31/12A61P31/10A61P33/06A61P29/00A61P9/00
CPCC07D251/18A61P35/00A61P31/12A61P31/10A61P33/06A61P29/00A61P9/00Y02A50/30
Inventor 王磊李正强李奉熙许雅宁王春宇苏佳瓅赵子先罗宸瀚宁宇杰
Owner JILIN UNIV
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