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(Z)-1-(1-substituted benzyl-5-methyl-1H-1,2,3-triazole-4-yl)-3-substituted benzyl-3-hydroxy-2-propylene-1-ketone compound and preparation method and application thereof

A compound, benzyl technology, applied in the field of HIV integrase inhibitors, can solve the problem of easy reduction of enol, and achieve the effect of mild reaction conditions

Inactive Publication Date: 2012-06-20
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology allows for easy access by making it easier than traditional methods that require expensive materials or complicated equipment. It works with commonly used chemicals at moderate temperatures without requiring extreme care during manufacturing processes.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding novel ways to develop an antiviral agent called integrated viruses that target multiple genes involved in disease progression without causing harmful side effects such as interference from other therapeutic agents like conventional therapies used against cancer.

Method used

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  • (Z)-1-(1-substituted benzyl-5-methyl-1H-1,2,3-triazole-4-yl)-3-substituted benzyl-3-hydroxy-2-propylene-1-ketone compound and preparation method and application thereof
  • (Z)-1-(1-substituted benzyl-5-methyl-1H-1,2,3-triazole-4-yl)-3-substituted benzyl-3-hydroxy-2-propylene-1-ketone compound and preparation method and application thereof
  • (Z)-1-(1-substituted benzyl-5-methyl-1H-1,2,3-triazole-4-yl)-3-substituted benzyl-3-hydroxy-2-propylene-1-ketone compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035](a) Synthesis of p-fluorobenzyl azide (1a)

[0036]

[0037] Add (1mmol, 0.189g) 4-fluorobenzyl bromide to a 50mL round bottom flask filled with 30mL acetone, stir at room temperature, then slowly add 10mL aqueous solution containing 2mmol sodium azide dropwise into the reaction system, and continue stirring at room temperature About 1 hour, TLC showed disappearance of starting material. The reaction solvent was removed under reduced pressure, dichloromethane extracted, anhydrous MgSO 4 Drying, desolvation.

[0038] The pure product is light yellow oily liquid, yield: 86%;

[0039] (b) Synthesis of 1-(1-(4-fluorobenzyl)-4-acetyl-5-methyl)-1H-1,2,3-triazole (2a)

[0040]

[0041] Place (10mmol, 1.51g) p-fluorobenzyl azide (1a), (10mmol, 1.0g) acetylacetone, (20mmol, 2.76g) anhydrous potassium carbonate in 15mL absolute ethanol and 15mL acetonitrile solution, stir and heat To 60°C, the reaction time was 2.5 hours, TLC showed that the starting material disappeared...

Embodiment 2

[0052] (a) Synthesis of p-fluorobenzyl azide (1a)

[0053] With embodiment 1.

[0054] (b) Synthesis of 1-(1-(4-fluorobenzyl)-4-acetyl-5-methyl)-1H-1,2,3-triazole (2a)

[0055] With embodiment 1.

[0056] (c) (Z)-1-(1-(4-fluorobenzyl)-5-methyl-1H-1,2,3-triazol-4-yl)-3-(4-methoxy Synthesis of substituted phenyl)-3-hydroxy-2-propen-1-one (3b)

[0057]

[0058] Under ice-bath conditions, (20mmol, 0.48g) sodium hydride was dissolved in 30mL dry tetrahydrofuran solution, and (10mmol, 2.33g) 10mL dry tetrahydrofuran solution of 1,2,3-triazole compound (2a) was added dropwise. After completion, (15mmol, 2.49g) 10mL dry tetrahydrofuran solution of methyl 4-methoxybenzoate was added dropwise, stirred and heated to 55°C, the reaction time was 3 hours, TLC showed that the raw material disappeared. After cooling, the reaction mixture was poured into ice water containing 5 mL of concentrated hydrochloric acid, extracted with 10 mL × 3 ethyl acetate, washed with brine, dried over anh...

Embodiment 3

[0069] (a) Synthesis of p-fluorobenzyl azide (1a)

[0070] With embodiment 1.

[0071] (b) Synthesis of 1-(1-(4-fluorobenzyl)-4-acetyl-5-methyl)-1H-1,2,3-triazole (2a)

[0072] With embodiment 1.

[0073] (c) (Z)-1-(1-(4-fluorobenzyl)-5-methyl-1H-1,2,3-triazol-4-yl)-3-(3,4-di Synthesis of methoxy-substituted phenyl)-3-hydroxy-2-propen-1-one (3c)

[0074]

[0075] Under ice-bath conditions, dissolve (20mmol, 0.48g) sodium hydride in 30mL dry tetrahydrofuran solution, add dropwise (10mmol, 2.33g) 10mL dry tetrahydrofuran solution of 1,2,3-triazole compound (2a), dropwise , followed by dropwise addition of (15mmol, 2.94g) 10mL dry tetrahydrofuran solution of methyl 3,4-dimethoxybenzoate, stirred and heated to 65°C, the reaction time was 2 hours, TLC showed that the raw material disappeared. After cooling, the reaction mixture was poured into ice water containing 5 mL of concentrated hydrochloric acid, extracted with 10 mL × 3 ethyl acetate, washed with brine, dried over an...

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Abstract

The invention relates to (Z)-1-(1-substituted benzyl-5-methyl-1H-1,2,3-triazole-4-yl)-3-substituted benzyl-3-hydroxy-2-propylene-1-ketone compound and a preparation method and an application thereof. The compound is expressed by formula (I), wherein R1 represents -F, R2 represents -H, or R1 represents -H, R2 represents -F; R3, R4 and R5 represent -OH or -H. The preparation method of the compound comprises synthesizing fluoro-benzyl azide with mono-fluoro benzyl bromide as raw material, reacting with acetylacetone to obtain 1-(1-fluoro-benzyl)-4-acetyl-5-methyl)-1H-1,2,3-triazole, carrying out condensation reaction with substituted methyl benzoate to obtain a compound having a dicarboxylic acid structure, and finally demethylating with boron tribromide to obtain the compound. The compound provided by the invention has an inhibitory action to HIV-1 (human immunodeficiency virus-1) integrase.

Description

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Claims

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Application Information

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Owner BEIJING UNIV OF TECH
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