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Substituted triazine compound as well as preparation method and application thereof

A technology for compounds and triazine derivatives, applied in the field of biomedicine, can solve the problems of boric acid sensitivity toxicity, the influence of detection reagents and temperature, and limited application, and achieve the effect of increasing water solubility and improving biological development prospects.

Pending Publication Date: 2022-05-27
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorescent sensors based on boric acid have the characteristics of simple synthesis and sensitive detection. However, boric acid is sensitive to environmental pH and has certain toxicity.
The fluorescence detection method of glycoprotein enzymes has the characteristics of high specificity and sensitivity, but is easily affected by detection reagents and temperature
The PMP sugar detection method has good sensitivity, but it needs to be detected in a strong alkaline environment, which limits its application in biological cells

Method used

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  • Substituted triazine compound as well as preparation method and application thereof
  • Substituted triazine compound as well as preparation method and application thereof
  • Substituted triazine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] In embodiment 1 structural formula (I), X 3 for O, R 3 For the preparation of alkylalkyne substituted triazine compounds and their quaternary ammonium salts:

[0051] Compound 1: 4-(4-(3-alkynyl-1-oxy)-1,3,5-triazin-2-yl)-4-methylmorpholin-4-amine hydrochloride

[0052] 2,4-Dichloro-1,3,5-triazine (500 mg, 3.4 mmol) was added to the reaction flask, 3-butyn-1-ol (5 mL) was added, and N,N-diisopropyl was slowly added dropwise Ethyl ethylamine (665 μL, 4.1 mmol), the solution changed from colorless to yellow and then red, and the reaction was stirred at room temperature for 30 min. It was extracted three times with ethyl acetate and saturated brine, and dried over anhydrous sodium sulfate. 500 mg was obtained by silica gel column chromatography, and the yield was 80%. MS(ESI): m / z, 250.1[M+H] + ; 1 H NMR (400MHz, Chloroform-d) δ8.74(s, 1H), 4.59(t, J=7.0Hz, 2H), 2.74(td, J=6.9, 2.7Hz, 2H), 2.05(t, J= 2.7Hz, 1H).

[0053] Add 2-(3-alkynyl-1-oxy)-4-chloro-1,3,5-triaz...

Embodiment 2

[0063] In embodiment 2 structural formula (I), X 3 for O, R 3 For the preparation of m-tolyl-substituted triazine compounds and their quaternary ammonium salts:

[0064] Compound 9: 2-Chloro-4-(m-tolyloxy)-1,3,5-triazine

[0065] 2,4-dichloro-1,3,5-triazine (500 mg, 3.4 mmol) and 5 mL of THF were added to the reaction flask for complete dissolution, and the mixture was stirred in an ice bath at 0°C. m-cresol (356 μL, 3.4 mmol) and DIPEA (665 μL, 4.1 mmol) were dissolved in 4 mL of THF, slowly added dropwise to the above reaction solution (the dropwise addition was completed in about 30 min), and the reaction was stirred at 0° C. for 30 min. It was extracted three times with ethyl acetate and saturated brine, and dried over anhydrous sodium sulfate. 590 mg was obtained by silica gel column chromatography, and the yield was 78.4%. MS(ESI): m / z, 222.0[M+H] + ; 1 H NMR (400MHz, Chloroform-d) δ 9.17 (s, 1H), 7.22 (t, J=7.5Hz, 1H), 7.05 (dt, J=7.5, 2.0Hz, 1H), 6.93 (dq, J= 8....

Embodiment 3

[0069] In embodiment 3 structural formula (I), X 3 for O, R 3 For the preparation of phenyl-substituted triazine compounds and their quaternary ammonium salts: the m-cresol used in the synthesis step of compound 9 is replaced with phenol, and according to the synthesis step of the second step of compound 1, N-methylmorpholine and The quaternary ammonium hydrochloride of pyridine can give compounds 12 and 13.

[0070] Compound 12: 4-methyl-4-(4-phenoxy-1,3,5-triazin-2-yl)morpholin-4-amine hydrochloride, 79% yield. MS(ESI): m / z, 274.1[M+H] + ; 1 H NMR (400MHz, Methanol-d 4 )δ9.10(s,1H),7.21(t,J=7.5Hz,2H),7.03-6.92(m,3H),4.48(ddd,J=12.0,10.3,7.0Hz,2H),4.43-4.33 (m, 2H), 4.21–4.11 (m, 2H), 4.05 (ddd, J=12.2, 6.3, 1.2Hz, 2H), 3.25 (s, 3H). 13 C NMR (101MHz, Methanol-d 4 ) δ177.14, 162.90, 160.20, 152.29, 129.39, 124.49, 121.64, 66.27, 49.68, 40.55.

[0071] Compound 13: 1-(4-phenoxy-1,3,5-triazin-2-yl)pyridin-1-amine hydrochloride in 69% yield. MS(ESI): m / z, 252.1[M+H] + ...

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Abstract

The invention provides a substituted triazine compound as well as a preparation method and application thereof, and belongs to the technical field of biological medicines. The substituted triazine derivative provided by the invention has a structural formula shown as a formula (II), the substituted triazine derivative provided by the invention can be effectively applied to aldose detection, and mass spectrum and HPLC (High Performance Liquid Chromatography) detection results show that the obtained substituted triazine compound can be well combined with aldose and has a good biological development prospect; the method can be used for preparing a sugar derivatization reagent.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a substituted triazine compound and a preparation method and application thereof. Background technique [0002] Sugar is the most basic and important substance in the life of the body, and all the physiological functions of the body are closely related to it. Most of the naturally occurring carbohydrates are not modified with luminescent groups and cannot be directly analyzed by UV or fluorescence detection techniques. With the continuous development of derivatization reagents, there are more and more sugar detection methods. For example, sugar fluorescence sensors mainly detect sugars according to changes in sugar concentration or fluorescence signals generated by sugar metabolites. The recognition molecule of sugar can be attached to the fluorescent carrier, thereby producing the corresponding fluorescent sensor of glucose including (1) enzyme, (2) boronic acid...

Claims

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Application Information

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IPC IPC(8): C07D251/16C07D401/12C07D401/04C07D405/14C07D405/12C07D251/18C07D405/04C07D251/22G01N33/00
CPCC07D251/16C07D401/12C07D401/04C07D405/14C07D405/12C07D251/18C07D405/04C07D251/22G01N33/00
Inventor 江涛王朝明
Owner OCEAN UNIV OF CHINA
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