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Chrysin-1,2,3-triazole compound having antibacterial activity, and its preparation method

A technology of antibacterial activity and chrysin, applied in botany equipment and methods, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problem of low activity, achieve high product yield, simple process, excellent antibacterial performance effect

Inactive Publication Date: 2013-04-24
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Chrysin (Chrysin, 5,7-dihydroxy-2-phenyl-4H-chromen-4-one, 5,7-dihydroxyflavone), as a widely distributed natural flavonoid, has various biological activities, such as antitumor, Anti-inflammatory, anti-bacterial, anti-anxiety, anti-oxidation, anti-ultraviolet, etc., but because of its low intestinal absorption and rapid glycosylation metabolism of the 5 and 7 hydroxyl groups, the activity is low. By modifying its structure, it can be synthesized Target molecules with high bioavailability, strong biological activity and low toxicity have become one of the important ways to create new drugs

Method used

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  • Chrysin-1,2,3-triazole compound having antibacterial activity, and its preparation method
  • Chrysin-1,2,3-triazole compound having antibacterial activity, and its preparation method
  • Chrysin-1,2,3-triazole compound having antibacterial activity, and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) 5-hydroxy-2-phenyl-7-(propyl-2-ynyl-1-yloxy)-4 H - Preparation of chroman-4-one

[0020]

[0021] Chrysin (30 mmol, 7.63 g) and 3-bromopropyne (30 mmol, 3.57 g) were placed in a 100 mL round bottom flask, and K 2 CO 3 (30 mmol, 4.15 g) and 50 mL of acetone, reflux, TLC to track the progress of the reaction, after the reaction is complete, filter, wash with acetone, spin dry, and purify by column chromatography to obtain a yellow solid with a yield of 87%.

[0022] (2) Preparation of o-methylazidobenzene

[0023]

[0024] Add a mixed solution of concentrated hydrochloric acid and water (14 mL, 1:1, v / v) into a 250 mL two-necked flask, add o-toluidine (22 mmol, 2.36 g), and stir until dissolved. At 0-5 °C, 8 mL of sodium nitrite (22 mmol, 1.52 g) in ice-water solution was slowly added dropwise. After 20 minutes, slowly add 18 mL of dissolved NaN 3 (22 mmol, 1.43 g) in water. After the dropwise addition, stir at room temperature, follow the reaction by thin...

Embodiment 2

[0030] 5-Hydroxy-2-phenyl-7-((1-(o-tolyl)-1 H -1,2,3-Triazol-4-yl)methoxy)-4 H - Preparation of chroman-4-one

[0031]

[0032]Add 5-hydroxy-2-phenyl-7-(propyl-2-ynyl-1-yloxy)-4 H - Chroman-4-one (0.68 mmol, 200 mg), o-methylazidobenzene (0.82 mmol, 109 mg) and water (3 mL). Then add catalyst cuprous sulfide (0.34 mmol), ultrasonic reaction at room temperature, TLC monitoring. After the reaction was complete, it was extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered with suction, precipitated, and subjected to column chromatography to obtain a light yellow solid with a yield of 85%.

Embodiment 3

[0034] 7-((1-(4-bromophenyl)-1 H -1,2,3-Triazol-4-yl)methoxy)-5-hydroxyl-2-phenyl-4 H - Preparation of chroman-4-one

[0035]

[0036] Add 5-hydroxy-2-phenyl-7-(propyl-2-ynyl-1-yloxy)-4 H - Chroman-4-one (0.68 mmol, 200 mg), p-bromoazidobenzene (0.68 mmol, 135 mg) and water (3 mL). Then add catalyst cuprous sulfide (0.34 mmol), ultrasonic reaction at room temperature, TLC monitoring. After the reaction was complete, it was extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered with suction, precipitated, and subjected to column chromatography to obtain a light yellow solid with a yield of 88%.

[0037] 1 H NMR (400 MHz, [D 6 ]DMSO): δ = 12.84 (s, 1H, OH), 9.04 (s, 1H, CH-H), 8.11 (d, J = 5.8 Hz, 2H, Ar-H), 7.91 (d, J = 8.1 Hz, 2H, Ar-H), 7.82 (d, J = 8.1 Hz, 2H, Ar-H), 7.65-7.59 (m, 3H, Ar-H), 7.06 (s, 1H, CH-H), 7.01 (s, 1H, Ar-H), 6.55 (s, 1H, Ar-H), 5.41 (s, 2H, CH 2 -H). ESI MS m / z : 490 [M+H] + .

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Abstract

The invention discloses a chrysin-1,2,3-triazole compound having an antibacterial activity, and its preparation method. A technical scheme adopted in the invention is mainly characterized in that the structural general formula of the chrysin-1,2,3-triazole compound having antibacterial activity is shown in the specification; and in the structural general formula, R can be a halogen atom, a halogenated alkyl group, an alkyl group, an alkoxy group or a nitro group, n1 is not less than 1, and n2 is not less than 0. The invention also discloses the preparation method of the compound, and uses of the compound. The chrysin-1,2,3-triazole compound has an excellent antibacterial performance, can be well used for controlling the animal and plant diseases caused by bacteria and fungi, and has great application prospects in the medicine field, the pesticide field and the like.

Description

technical field [0001] The invention relates to the technical field of antibacterial active compounds and synthesis methods thereof, in particular to a chrysin-1,2,3-triazole compound with antibacterial activity and a preparation method thereof. Background technique [0002] Since the discovery of the bactericidal activity of azole compounds in the 1960s, the compounds have reached a new level in the prevention and control of harmful animal and plant pathogens. In the 1970s, the high-efficiency bactericidal activity of triazole compounds attracted people's attention, and major companies developed and researched them one after another. So far, a variety of fungicides have been developed, which have the advantages of less impact on the environment, strong selectivity to diseases, and high curative effect. In recent years, the structure of newly developed triazole fungicides has the following characteristics: with multi-substituted triazoles as the mother nucleus, these compou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A01N43/647A01P3/00A01P1/00A61K31/4192A61P31/10A61P31/04
Inventor 姜玉钦徐桂清吕晓孟张玮玮过治军李伟梁璐璐姜蓉蓉师灵娜
Owner HENAN NORMAL UNIV
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