A kind of s-triazine derivative compound containing s-tetrazine ring and its preparation method

A compound, the technology of s-triazine, which is applied in the field of drug synthesis and medicine, can solve problems such as compounds that have not been reported on s-triazine derivatives, and achieve high biological activity.

Inactive Publication Date: 2011-12-07
ZHEJIANG LEPU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the prior art reports more on compounds such as diamine or triamine triazine derivatives, there is no report on compounds containing s-tetrazine ring-containing s-triazine derivatives, while containing s-tetrazine rings The derivatives of the s-triazine series are a new type of derivatives of the triazine series

Method used

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  • A kind of s-triazine derivative compound containing s-tetrazine ring and its preparation method
  • A kind of s-triazine derivative compound containing s-tetrazine ring and its preparation method
  • A kind of s-triazine derivative compound containing s-tetrazine ring and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] 4-Chloro-6-(2-(6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl)hydrazino)- Preparation of N-isobutyl-1,3,5-triazine-2-amine (Xu-1)

[0057]

[0058] Add 1.25 mmol of cyanuric chloride and 3.7 mmol of potassium carbonate into 30 ml of dioxane, stir, cool down to -5 ° C to 0 ° C, and start to slowly add the mixed solution (6-(3,5-dimethylpyridine) oxazol-1-yl)-3-hydrazine-1,2,4,5-tetrazine 1.25mmol dissolved in 20ml dioxane mixed solution), the reaction temperature was controlled to -5℃~3℃ during the dropwise addition, After the dropwise addition, the temperature was controlled at 2°C to 8°C, and the halogenation reaction was continued for 2 hours. After the reaction was completed, 2.5 mmol of isobutylamine was added to the reaction solution, and the temperature was heated to 100°C for reflux, and the reflux reaction was performed for 10 hours. , start cooling, suction filtration, remove the solid matter in the system, collect the filtrate, remove the solvent d...

Embodiment 2

[0065] 4-Chloro-6-(2-(6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl)hydrazino)- Preparation of N-isopropyl-1,3,5-triazin-2-amine (Xu-2)

[0066]

[0067] Add 1.25 mmol of cyanuric chloride and 3.7 mmol of potassium carbonate into 30 ml of dioxane, stir, cool down to -5 °C to 0 °C, and start to slowly dropwise add 6-(3,5-dimethylpyrazole-1 - base)-3-hydrazino-1,2,4,5-tetrazine 1.25mmol dissolved in 20ml of dioxane mixed solution, control the reaction temperature during the dropwise addition -5 ℃ ~ 3 ℃, after the dropwise addition , control the temperature at 0 ℃ ~ 5 ℃, continue to stir the halogenation reaction for 1h, after the reaction is over, add 2.5mmol isopropylamine to the reaction solution, heat up to 100 ℃ reflux, reflux reaction for 10h, after the reaction is over, start cooling, pumping Filtration to remove the solid matter in the system, collect the filtrate, distill under reduced pressure to remove the solvent dioxane, after the distillation, add an ap...

Embodiment 3

[0074] 4-Chloro-6-(2-(6-morpholino-1,2,4,5-tetrazin-3-yl)hydrazino)-N,N-dipropyl-1,3,5-tri Preparation of oxazine-2-amine (Xu-3)

[0075]

[0076] Add 1.25mmol of cyanuric chloride and 3.7mmol of potassium carbonate to 30ml of dioxane, stir, cool down to -5℃~0℃, start to slowly dropwise add 6-morpholinyl-3-hydrazino-1,2 , 1.25mmol of 4,5-tetrazine is dissolved in a mixed solution of 20ml of dioxane, and the reaction temperature is controlled at -5℃~3℃ during the dropwise addition. Substitute the reaction for 2h, after the reaction is over, add 2.5mmol of di-n-propylamine to the reaction solution, heat up to reflux, reflux for 8h, after the reaction is over, start cooling, suction filtration, remove the solid matter in the system, collect the filtrate, and remove by distillation The solvent dioxane in the filtrate was removed, after the distillation was completed, an appropriate amount of ethyl acetate was added, and then a saturated aqueous sodium chloride solution was add...

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Abstract

The invention relates to sym-triazine derivative compounds containing sym-tetrazine rings and a preparation method thereof and belongs to the technical field of pharmaceutical synthesis and medicines. The sym-triazine derivative compounds containing sym-tetrazine rings provided by the invention are new sym-triazine derivative compounds containing sym-tetrazine rings with higher biological activity and a certain inhibition effect on tumor cells, and are synthesized from cyanuric chloride, substituted sym-tetrazine hydrazine and di-substituted ammonia used as raw materials by the synthesis method. The synthesis method has the advantages of readily available raw materials, simple and convenience process, easiness for operation and lower synthesis cost, and is suitable for industrial production. Through in-vitro test of the inhibition effect on the tumor cells, the sym-triazine derivative compounds containing sym-tetrazine rings provided by the invention have stronger inhibition effect onthe tumor cells, such as human fibrosarcoma, human breast cancer, human lung cancer, human colon cancer and other tumor cells.

Description

technical field [0001] The invention relates to a s-triazine derivative compound, in particular to a s-triazine derivative compound containing an s-tetrazine ring and a preparation method thereof, belonging to the technical field of drug synthesis and medicine. Background technique [0002] Compounds such as triazine derivatives have attracted extensive research by many scholars and researchers due to their wide range of biological activities, especially the advantages of s-triazine derivatives in antitumor activity. [0003] A novel 2-hydroxy-4,6-diamino-[1,3,5]triazine as reported by Baindur N. et al. in Journal of medicinal chemistry, 2005, 48(6), 1717-1720. compounds in which 2-hydroxy-4-benzo[d]thiazole-6-[benzyl(isopropyl)]-1,3,5-triazine-4,6-diaminop-tyrosine kinase The inhibition rate reached 0.018 μM (IC 50 ); another example is the 2,4,6-triaryl-1,3,5-triazine-2,4 reported by Arya, K. et al in Bioorganic & Medicinal Chemistry Letters, 2007, 17, 3298-3304. 6-tria...

Claims

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Application Information

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IPC IPC(8): C07D403/14C07D403/12A61P35/00
Inventor 徐峰杨珍珍蒋军荣柯中炉奚立民
Owner ZHEJIANG LEPU PHARMA CO LTD
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