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4-amino-pyrrolotriazine derivative and preparation method and application thereof

A technology of triazine derivatives and derivatives, which is applied in the direction of active ingredients of hydroxyl compounds, drug combinations, and pharmaceutical formulations, can solve the problems of candidate inhibitors not appearing, and achieve good inhibitory and anti-tumor effects

Active Publication Date: 2020-11-20
TIANJIN QUANHECHENG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, although a variety of CDC25B inhibitors have been reported, and some promising progress has been made, there are no clinically active candidates in this field Inhibitors did not appear

Method used

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  • 4-amino-pyrrolotriazine derivative and preparation method and application thereof
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  • 4-amino-pyrrolotriazine derivative and preparation method and application thereof

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Embodiment 1

[0029] A preparation method of 4-amino-pyrrolotriazine derivatives and its antitumor test,

[0030] Preparation of ferulic acid derivatives: Dissolve ferulic acid in sodium hydroxide solution, stir for 2 hours under ice bath, add p-hydroxybenzoyl chloride, stir and react at 100°C for 5 hours, adjust pH to 6. 5. Suction filtration, washing with water, and drying to obtain ferulic acid derivatives; the addition amount of ferulic acid is 16wt% of the sodium hydroxide solution; the mass fraction of the sodium hydroxide solution is 10wt%; the addition amount of p-hydroxybenzoyl chloride It is 90wt% of ferulic acid.

[0031] Preparation of acyl chloride ferulic acid derivatives: Add ferulic acid derivatives into dichloromethane, stir and mix, add initiator dimethylaminoformamide, reflux reaction for 1 hour, add oxalyl chloride, stir and reflux reaction for 6 hours, after the reaction is completed , evaporated to dryness, then added dichloromethane and evaporated to dry oxalyl chlor...

Embodiment 2

[0035] A preparation method of 4-amino-pyrrolotriazine derivatives and its antitumor test,

[0036] Preparation of ferulic acid derivatives: Dissolve ferulic acid in sodium hydroxide solution, stir for 2 hours under ice bath, add p-hydroxybenzoyl chloride, stir and react at 100°C for 5 hours, adjust pH to 6. 5. Suction filtration, washing with water, and drying to obtain ferulic acid derivatives; the addition amount of ferulic acid is 16wt% of the sodium hydroxide solution; the mass fraction of the sodium hydroxide solution is 10wt%; the addition amount of p-hydroxybenzoyl chloride It is 90wt% of ferulic acid.

[0037]Preparation of acyl chloride ferulic acid derivatives: Add ferulic acid derivatives into dichloromethane, stir and mix, add initiator dimethylaminoformamide, reflux reaction for 1 hour, add oxalyl chloride, stir and reflux reaction for 6 hours, after the reaction is completed , evaporated to dryness, then added dichloromethane and evaporated to dry oxalyl chlori...

Embodiment 3

[0041] A preparation method of 4-amino-pyrrolotriazine derivatives and its antitumor test,

[0042] Preparation of ferulic acid derivatives: Dissolve ferulic acid in sodium hydroxide solution, stir for 2 hours under ice bath, add p-hydroxybenzoyl chloride, stir and react at 100°C for 5 hours, adjust pH to 6. 5. Suction filtration, washing with water, and drying to obtain ferulic acid derivatives; the addition amount of ferulic acid is 16wt% of the sodium hydroxide solution; the mass fraction of the sodium hydroxide solution is 10wt%; the addition amount of p-hydroxybenzoyl chloride It is 90wt% of ferulic acid.

[0043] Preparation of acyl chloride ferulic acid derivatives: Add ferulic acid derivatives into dichloromethane, stir and mix, add initiator dimethylaminoformamide, reflux reaction for 1 hour, add oxalyl chloride, stir and reflux reaction for 6 hours, after the reaction is completed , evaporated to dryness, then added dichloromethane and evaporated to dry oxalyl chlor...

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Abstract

The invention discloses a 4-amino-pyrrolotriazine derivative and a preparation method and application thereof. The 4-amino-pyrrolotriazine derivative is composed of a ferulic acid derivative part anda 4-amino-pyrrolotriazine part, and the structural formula of the 4-amino-pyrrolotriazine derivative is shown in the specification. The preparation method of the 4-amino-pyrrolotriazine derivative comprises the following steps: firstly, preparing a ferulic acid derivative from ferulic acid and p-hydroxybenzoyl chloride, performing acylating chlorination on the ferulic acid derivative by using oxalyl chloride, and then reacting with 4-amino-pyrrolotriazine to generate the 4-amino-pyrrolotriazine derivative. The 4-amino-pyrrolotriazine derivative obtained by the preparation method disclosed by the invention has a good anti-tumor effect, the IC50 concentration of the 1, 4-amino-pyrrolotriazine derivative in anti-tumor cells is not higher than 12 [mu] M, the inhibition effect on CDC25B is good, the inhibition effect at least reaches 95%, meanwhile, the 1, 4-amino-pyrrolotriazine derivative has an antibacterial effect, and the inhibition zone at least reaches 10 mm.

Description

technical field [0001] The invention relates to a 4-amino-pyrrolotriazine derivative, a preparation method and application thereof. Background technique [0002] In today's world, cancer has become a rapidly growing epidemic disease, seriously affecting human health. Therefore, governments of various countries have paid great attention to tumor research for a long time, and significant progress has been made in many aspects. Drug therapy is the fastest-growing tumor therapy, and it has become one of the important methods for clinical treatment of malignant tumors. Therapies targeting tumorigenesis mechanisms, key signaling pathways, and regulatory factors have specific antitumor effects. And the toxicity is significantly reduced, which is the hot spot of current tumor research and an important research direction to solve the current clinical treatment problems of tumors. Cell cycle disorder is the most important mechanism of tumorigenesis. Overexpression of the regulator...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P35/00A61P31/04A61P37/04A61K31/53A61K31/7048A61K31/045
CPCC07D487/04A61P35/00A61P31/04A61P37/04A61K31/53A61K31/7048A61K31/045A61K2300/00
Inventor 宋艳民陈勇张超
Owner TIANJIN QUANHECHENG TECH