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3-substituted-1-methyl-quinazoline-2,4-dione compounds, preparation method and application thereof

A technology for quinazoline dione and compound, applied in the field of preparation of the compound, can solve the problems of reduced therapeutic effect, loss, increase of bacterial drug resistance, etc., and achieves the solution of bacterial drug resistance, simple preparation method, and easy-to-obtain raw materials Effect

Inactive Publication Date: 2014-04-23
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Anti-infective drugs are currently one of the most widely used drugs in clinical practice. While curing and saving the lives of many patients, due to long-term, large-scale, irrational use and even abuse, bacterial drug resistance is greatly increased, and the therapeutic effect is gradually reduced. Even completely lost, have a great impact on the patient's recovery

Method used

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  • 3-substituted-1-methyl-quinazoline-2,4-dione compounds, preparation method and application thereof
  • 3-substituted-1-methyl-quinazoline-2,4-dione compounds, preparation method and application thereof
  • 3-substituted-1-methyl-quinazoline-2,4-dione compounds, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1, the preparation of 1-methyl-2 shown in general formula I, 4 (1H, 3H)-quinazoline diketones

[0024] 1, the preparation of intermediate 2 (methyl o-thaminobenzoate)

[0025]

[0026] In a 250ml flask with a drying tube, add 16g of raw material 1 (methyl anthranilate) and 80ml of dimethylformamide (DMF), then dropwise add a mixture of 15.6g of iodomethane and 20ml of DMF, and add to room temperature React for 1 hour, then heat to 50°C and react for 7 hours. After the reaction, cool to room temperature, add 200ml of water, extract with ethyl acetate (3×60ml), combine the ethyl acetate extracts, dry over anhydrous magnesium sulfate, and filter with suction , the filtrate was rotary evaporated to remove the solvent, and 11.646 g of intermediate 2 (yellow liquid) was obtained, with a yield of 66.7%.

[0027] 2, the preparation of intermediate 3 (o-methylaminobenzoic acid)

[0028]

[0029] In a 250ml flask, add 29.242g of intermediates, 40ml of water, 30...

Embodiment 2

[0066] The antimicrobial activity of 1-methyl-2 shown in embodiment 2, general formula I, 4 (1H, 3H)-quinazoline diketones

[0067] After dissolving the compounds 9a-m prepared in Example 1 with a small amount of dimethyl sulfoxide, they were diluted with sterile water to make a solution of a certain concentration, and then diluted with water to prepare a series of sample solutions with gradient concentrations. Set streptomycin sulfate and polyoxin D as positive controls; pour the sterilized agar solid medium into the plate, and after cooling, spread 50 μl of the bacterial solution evenly on the surface of the agar, and then apply the sample solution with different concentrations The soaked filter paper pieces were pasted on the surface of the agar, cultured at 37°C for 24 hours (bacteria) or 25°C for 48 hours (fungus), and the minimum inhibitory concentration (MIC) was determined. The results are shown in Table 1

[0068] Antimicrobial activity (MIC, μg / ml) of table 13-subst...

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Abstract

The invention discloses 3-substituted-1-methyl-quinazoline-2,4-dione compounds shown in formula 1, a preparation method and application of the 3-substituted-1-methyl-quinazoline-2,4-dione compounds. Through in-vitro anti-microbial activity test, it is found that these compounds have certain inhibitory activity on gram-positive bacteria (Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Bacillus subtilis), gram-negative bacteria (Escherichia coli, proteusbacillus vulgaris, Pseudomonas aeruginosa) and fungus (Nostoc, Candida Albicans). Inhibitory activities of partial compounds on partial tested strains are approximate to or even superior to those of existing drugs such as streptomycin sulfate and polyoxin D. The compounds are especially sensitive to methicillin-resistant Staphylococcus aureus, can be prepared into antibacterial and / or anti-fungal drugs, and have the advantages of simple preparation method, easily-accessible materials and low cost.

Description

technical field [0001] The invention belongs to the field of chemistry, relates to a new class of organic compound, and also relates to the preparation method and medical application of the compound. Background technique [0002] Anti-infective drugs are currently one of the most widely used drugs in clinical practice. While curing and saving the lives of many patients, due to long-term, large-scale, irrational use and even abuse, bacterial drug resistance is greatly increased, and the therapeutic effect is gradually reduced. Even complete loss has a great impact on the recovery of patients. Therefore, it is necessary to continuously develop new and highly effective anti-infective drugs. [0003] With the change of structure, quinazolinedione compounds can display various activities, such as antibacterial, herbicide, insecticide, etc., and can be used as serotonin receptor antagonist, α-adrenergic receptor antagonist, platelet ADP receptor antagonist Drugs, acetylcholine r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/96A61K31/513A61P31/04A61P31/10
CPCY02A50/30
Inventor 吉庆刚杨丹
Owner SOUTHWEST UNIV
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