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Antibacterial compound as well as preparation method and application thereof

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

Inactive Publication Date: 2015-07-22
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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  • Antibacterial compound as well as preparation method and application thereof
  • Antibacterial compound as well as preparation method and application thereof
  • Antibacterial compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of 2-Methyl-4-(4-Acetoxybenzylidene)oxazolone

[0021] Add 0.1 mol of p-hydroxybenzaldehyde, 0.13 mol of acetylglycine, 0.12 mol of anhydrous sodium acetate and 50 g of acetic anhydride into a 100 mL three-necked flask in sequence, control the temperature at 90°C, stir for 5 h, and cool to room temperature. The solution became solid, filtered with suction, the filter cake was washed with cold water, and the filter cake was dried to obtain 24.5 g of yellow powder with a yield of 100%, ESI-MS (m / z): 246.2.

Embodiment 2

[0023] 3,4-dihydro-6-(4-hydroxybenzyl)-3-thio-1,2,4-triazine-5(2 H ) - Preparation of ketones

[0024] Mix 2-methyl-4-(4-acetoxybenzylidene)oxazolone (0.1mol, 24.5g) and KOH (11.2g) in 500ml of water, heat in a water bath, and let it reflux for 6 hours, The reaction solution became clear, and then thiosemicarbazide (0.12 mol, 9 g) was added, and the mixture was reacted for 4.5 hours. Afterwards, the pH of the reaction solution was adjusted with acetic acid to make it pH 4, and a solid was precipitated, which was filtered and dried to obtain 15.7 g of a yellow powder. Yield 66.8%, ESI-MS (m / z): 236.1 (M+H) + .

Embodiment 3

[0026] 3-(4-acetylphenyl)-6-(4-hydroxybenzyl)-7 H - Preparation of thiazolo[3,2-b]-1,2,4-triazin-7-one (L1)

[0027] 3,4-dihydro-6-(4-hydroxybenzyl)-3-thio-1,2,4-triazine-5(2 H )-ketone 0.01 mol, 4-acetyl-α-chloroacetophenone 0.01 mol was added to 50 mL of glacial acetic acid, stirred and refluxed for 26 h, after the reaction was monitored by TLC, cooled to room temperature, the reaction liquid gradually precipitated solid, pumped Filter, after washing with water, ethanol recrystallization, obtain white crystal 2.12 grams, yield 56.23%,

[0028] 1 H-NMR (600 MHz, DMSO- d 6 ): δ 10.01 (1H, s), 7.48 (2H, d, J = 8.4Hz), 7.33 (1H, s), 7.21 (2H, d, J = 8.4Hz), 6.87 (2H, d, J = 8.4Hz), 6.80 (2H, d, J = 8.4Hz), 3.91 (2H, s), 2.76 (3H, s); ESI-MS (m / z): 378.0 (M+H) + .

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Abstract

The invention discloses application of a 3-aryl-6-aryl-7H-thiazolo [3,2-b]-1,2,4-triazine-7-ketone derivative with a general formula I shown in the description to an antibacterial drug. In the general formula I, R1 and R2 are methyl, halogen, hydroxyl, methoxyl, acetyl, propionyl, formylphenyl, carbamoyl-methoxy-benzyl, 4-methylanilino formyl-methoxyl or chloroaniline formyl-methoxyl respectively and independently. The 3-aryl-6-aryl-7H-thiazolo [3,2-b]-1,2,4-triazine-7-ketone derivative, namely an antibacterial compound provided by the invention, has obvious inhibiting effects on methicillin-resistant staphylococcus aureus, escherichia coli, pseudomonas aeruginosa and a variety of bacteria, and can be used for the preparation of the antibacterial drug.

Description

technical field [0001] The present invention relates to the field of chemical and pharmaceutical technology, in particular to 3-aryl-6-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one 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, a variety of drug-...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61P31/04
CPCC07D513/04Y02A50/30
Inventor 刘斯婕何敬宇张宝华贾鹏飞史兰香
Owner SHIJIAZHUANG UNIVERSITY
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