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Compound with antibacterial ability as well as preparation method and application thereof

A technology of compounds and capabilities, applied in the fields of organic chemistry, antibacterial drugs, resistance to vector-borne diseases, etc., can solve problems such as the crisis of effective clinical application of antibacterial drugs

Inactive Publication Date: 2015-07-29
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The emergence of these drug-resistant strains puts the effective clinical use of existing antibacterial drugs in crisis

Method used

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  • Compound with antibacterial ability as well as preparation method and application thereof
  • Compound with antibacterial ability as well as preparation method and application thereof
  • Compound with antibacterial ability as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of 2-methyl-4-(4-chlorobenzylidene)oxazolone

[0024] Add 0.1 mol of p-chlorobenzaldehyde, 0.13 mol of acetylglycine, 0.12 mol of anhydrous sodium acetate and 50 g of acetic anhydride into a 100 mL three-neck flask in sequence, control the temperature at 90°C, stir for 5 h, and cool to room temperature. The solution became solid, suction filtered, the filter cake was washed with cold water, and the filter cake was dried to obtain 22.1 g of yellow powder, the yield was 100%, ESI-MS (m / z): 222.2 (M+H) + .

Embodiment 2

[0026] 3,4-dihydro-6-(4-chlorobenzyl)-3-thio-1,2,4-triazine-5(2 H ) - Preparation of ketones

[0027] Mix 2-methyl-4-(4-chlorobenzylidene)oxazolone (0.1mol, 22.1g) and KOH (11.2g) in 500ml of water, heat in a water bath, and let it reflux for 6 hours, and the reaction solution It became clear, then added thiosemicarbazide (0.12mol, 9g), and the mixture was reacted for 4.5h, then the pH of the reaction solution was adjusted with acetic acid to make it pH 4, and a solid precipitated, which was filtered and dried to obtain 13.5g of yellow powder, with a yield of 53.42 %, ESI-MS (m / z): 254.1 (M+H) + .

Embodiment 3

[0029] 2-(4-Chlorobenzyl)-9-(4-methoxybenzoyl)-6,7-dihydro-3H-[1,2,4]triazino[1,3]thiazepine Preparation of Zol-3-one (L1)

[0030] 3,4-dihydro-6-(4-chlorobenzyl)-3-thio-1,2,4-triazine-5(2 H )-ketone 0.01 mol, add 50 mL ethanol to dissolve, add dropwise 1-(4-methoxybenzoyl)-4-bromo-1-butyne 0.01 mol and triethylamine under stirring, reflux reaction for 3h, TLC monitoring After the reaction was completed, it was cooled to room temperature, and the reaction solution gradually precipitated solids. After suction filtration, washing with water, and ethanol recrystallization, 2.32 g of white crystals were obtained, with a yield of 52.74%. 1 H-NMR (600 MHz, DMSO- d 6 ): δ7.80 (2H, d, J = 8.4Hz), 7.48 (2H, d, J = 8.4Hz), 7.33 (1H, s), 7.21 (2H, d, J = 8.4Hz), 7.17 (2H, d, J = 8.4Hz), 3.91 (2H, s), 3.80 (3H, s), 2.63 (2H, m), 2.60 (3H, m); ESI-MS (m / z): 439.9 (M+H) + .

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Abstract

The invention discloses an application of a 2-aryl-9-aryl-6,7-dihydro-3H-[1,2,4]triazine[1,3]thiazepine-3-ketone derivative represented by the general formula I shown in the specification to antibacterial drugs. R1 and R2 are hydrogen, a methoxy group, a nitro group, a methyl group, halogen, a hydroxyl group, an acetyl group, a propionyl group, a benzoyl group, an alkoxy group, an amino alcoxy group and a carbamyl alkoxy group independently. The compound has an obvious inhibition effect on various bacteria such as MRSA (methicillin-resistant staphylococcus aureus), Escherichia coli, pseudomonas aeruginosa and the like and can be applied to preparation of the antibacterial drugs.

Description

technical field [0001] The present invention relates to the field of chemical and pharmaceutical technology, in particular to 2-aryl-9-aryl-6,7-dihydro-3H-[1,2,4]triazino[1,3]thiazepine-3 - Ketone derivatives and their application in the preparation of antibacterial drugs. Background technique [0002] Since penicillin was used clinically in the 1940s, antibiotics have saved countless lives, and penicillin has thus become one of the greatest human discoveries in the 20th century, and opened up a new era of antibiotic research. Cephalosporins, quinolones, Various types of antibiotics such as macrolides and aminoglycosides. It is true that we have such a wide variety of antibacterial drugs, but with the abuse of antibiotics, the problem of bacterial drug resistance has become increasingly prominent. In fact, almost all antibiotics have been challenged by corresponding drug-resistant strains. Since New Grinea discovered penicillin-resistant Streptococcus pneumoniae in 1967, ...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61P31/04
CPCC07D513/04Y02A50/30
Inventor 刘斯婕张宝华贾鹏飞岳红坤周冉
Owner SHIJIAZHUANG UNIVERSITY
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