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4,5-glyoxalidine [1,2-a] quinoline derivative and application of 4,5- glyoxalidine [1,2-a] quinoline derivative

A technology of dihydroimidazole and 2-a, applied in medical preparations containing active ingredients, organic active ingredients, organic chemistry, etc., can solve the problems of bacterial drug resistance and other issues

Inactive Publication Date: 2013-01-30
HEILONGJIANG BAYI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The first object of the present invention is to provide a kind of 4,5-dihydroimidazolium [1,2-a] quinoline derivatives, solve the problem that the application of current antibiotics is limited, easily lead to bacterial drug resistance, resulting in the need to synthesize new The problem with antimicrobials

Method used

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  • 4,5-glyoxalidine [1,2-a] quinoline derivative and application of 4,5- glyoxalidine [1,2-a] quinoline derivative
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  • 4,5-glyoxalidine [1,2-a] quinoline derivative and application of 4,5- glyoxalidine [1,2-a] quinoline derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] [Example 1] Preparation of 6-benzyloxy-3,4-dihydro-1H-quinolin-2-one

[0074] Put benzyl chloride (113g, 0.90mol) into a round bottom flask, add sodium hydroxide (36g, 0.90mol) and 6-hydroxy-3,4-dihydro-1H-quinolin-2-one (13.0g ,0.80mol), and then add anhydrous absolute ethanol (500mL), the reaction solution was heated to reflux for 20h, and the reaction was verified to be complete by TLC. The solvent was evaporated, and the residue was poured into ice water, filtered, and dried to obtain a white powder.

Embodiment 2

[0075] [Example 2] Preparation of 6-benzyloxy-3,4-dihydro-1H-quinoline-2-thione

[0076] Acetonitrile (900 mL) and triethylamine (300 mL) were poured into a round bottom flask. Under an ice-water bath, add phosphorus pentasulfide (166g, 0.75mol) in batches and keep stirring. After the phosphorus pentasulfide is completely dissolved, add the compound 6-benzyloxy-3,4-dihydro-1H-quinolin-2-one (180g, 0.75mol). The reaction was stirred at reflux for 12h. The solvent was evaporated under reduced pressure, and the residue was recrystallized from anhydrous ethanol to obtain a yellow powder.

Embodiment 3

[0077] [Example 3] Preparation of 7-benzyloxy-4,5-dihydroimidazo[1,2-a]quinoline

[0078] 6-Benzyloxy-3,4-dihydro-1H-quinoline-2-thione (110g, 0.43mol), aminoacetaldehyde dimethyl acetal (45g, 0.43mol) and triethylamine ( 101g, 1mol) into a round bottom flask, then added anhydrous ethanol (300mL), the reaction solution was heated to reflux for 24h. The completion of the reaction was verified by TLC chromatography. The solvent was evaporated, acetic acid (150 mL) was added to the residue, and reacted at 100° C. for 4 h, and the reaction was verified to be complete by TLC. The solvent was evaporated, and the pure product was separated by column chromatography to obtain 40.56g, with a yield of 36%.

[0079] 1 H-NMR (400MHz, CD 2 Cl 2 )δ:2.88-3.09(m,4H,H-4,H-5),5.08(s,2H,-OCH 2 -),6.91-7.05(m,2H,H-6,H-8),7.19-7.22(d,1H,H-9),7.31-7.42(m,5H,Ar-H),7.48-7.50( m,2H,H-1,H-2).MS m / z 277(M+1).

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Abstract

The invention relates to a 4,5-glyoxalidine [1,2-a] quinoline derivative shown as the following formula (1) and application of the 4,5- glyoxalidine [1,2-a] quinoline derivative, wherein R represents C1-C12 alkyls, benzyl and substituted benzyl, Y represents H, O and N, and R1 represents C1-C12 alkyls, phenyl, substituted phenyl, benzyl and substituted benzyl. The invention also provides a medicine composition containing the derivative and salts of the derivative, and application of the derivative and the salts of the derivative to antibacterial medicine preparation. The derivative and the salts of the derivative respectively have the inhibition effects on staphylococcus aureus, escherichia coli, other gram-negative bacteria (such as pseudomonas aeruginosa, Klebsiella pneumoniae, proteusbacillus vulgaris, salmonella and pasteurella) and gram-positive bacteria, and in other aspects, the antibacterial effect is better than that of ciprofloxacin and amoxicillin.

Description

technical field [0001] The invention belongs to the field of new compound drugs, and relates to a 4,5-dihydroimidazo[1,2-a]quinoline derivative and its application in the preparation of antibacterial drugs. Background technique [0002] The development of antimicrobial drugs in the 20th century was brilliant. In the mid-1930s, sulfonamide drugs entered the clinic. In the early 1940s, penicillin was discovered, and a large number of important antibiotics such as chloramphenicol, tetracycline, and macrolide were discovered immediately, and then semi-synthetic penicillins, cephalosporins, and quinolone antibacterial drugs came out. , making it possible to effectively treat various bacterial infections, and making outstanding contributions to safeguarding human health and prolonging life. With the widespread use of antibiotics, two problems have emerged in clinical practice: one is that bacterial drug resistance has increased year by year, resulting in reduced efficacy or even ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/4745A61P31/04
CPCY02A50/30
Inventor 孙先宇贺显晶温翔刘艳鹏邹云鹏李健周长平
Owner HEILONGJIANG BAYI AGRICULTURAL UNIVERSITY
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