7-acetoxy-6-bromo-3-formylchromones, have an antimicrobial effect against staphylococcus and spore flora that do not affect intestinal flora

 

(57) Abstract:

Usage: in medicine as an antimicrobial agent against staphyloccocus and spore flora that do not affect intestinal flora. Essence: 7-acetoxy-6-bromo-3-formylchromones. B. F. C12H7Br O5. So pl. 243oC. Reagent 1: 2-hydroxy-4-acetoxy-acetophenone. Reagent 2: complex Vilsmaier followed by cyclization. table 2.

The invention relates to chemical-pharmaceutical industry, namely, to new biologically active substances on the basis of which can be created drugs that have antimicrobial activity.

The claimed connection is a new derivative chromone, namely, 7-acetoxy-6-bromo-3-formylchromones

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Cited in the application connection properties and biological activity not described in literature.

The closest structural analogues to the claimed compound are substituted chroman-3-aldehydes having antiallergic activity [1] Similar in structure and action is ocalenia acid 1-ethyl-1,4-dihydro-6,7 - methylenedioxy-4-oxoindole-3-carbon - Wai acid corresponding to the formula

used for infections of the Sabbath. The aim of the invention is to obtain a new derivative chromone, with more pronounced antimicrobial activity.

The goal has been achieved by the synthesis of the compounds of formula

get beforeleaving 2-hydroxy-4 - acetoxystyrene complex of Vilsmeier with subsequent cyclization.

P R I m e R 1. 7-Acetoxy-6-bromo-3-formylchromones.

In a two-neck flask equipped with addition funnel, thermometer and potassium chloride tube, 20 ml of fresh N,N - dimethylformamide under ice cooling are added dropwise to 11.4 ml (0.05 M) of phosphorus oxychloride (U), then the mixture is left to stand for 30 min in the dark place. Then the flask on the magnetic stirrer and to the resulting reagent Vilsmeier under ice cooling and stirring, added dropwise a solution of 1.94 g (0.01 M) 2-hydroxy-4 - acetoxystyrene in 20 ml of DMF. The rate of addition of regulate so that the temperature did not rise above 10-15aboutC. Stirring is continued for another 1 h, then thickened the reaction mixture was poured into ice-cold water. The precipitation is sucked off over a Buechner funnel, washed with water until neutral and with three portions of cold ethanol (10 ml). The crude drug is dried and crystallized,8.

Calculated From 46.3; H Of 2.26; Br 25,7; 25,7.

The IR-spectrum, liquid paraffin: 1760 cm-1(ASO)

1695 cm-1(SNO)

1650 cm-1(C=O)

1615 cm-1(C=C)

Number of state registration 10513192.

Study of antimicrobial activity was carried out at the Department of physiology, pathology and Microbiology Pyatigorsk pharmaceutical Institute according to the following procedure:

In a sterile tube was placed a portion of the compounds, equal to 32 mg and dissolve it in 5 ml of DMSO, receiving a solution containing 6400 g/ml of the substance. From the basic solution was prepared interim solution containing 1600 mcg/ml number of vials of sterile molten nutrient agar (20 ml in each vial) was added a measured amount of a primary or intermediate solution to obtain a concentration of the substance in the medium from 320 to 20 mcg/ml After mixing the contents of each vial were poured into a sterile Petri dish and after drying for 1 day was a series with decreasing concentrations of the drug in the medium and by sector produced seeding suspension 12 of the test cultures (listed in table 2) in the amount of one ear bacterial loop.

Crops his crops on nutrient agar (PA) without drugs, nutrient agar with the addition of solvent, nutrient agar with the addition of norsulfazola and similar in structure and action of 7-hydroxy-6-bromo-4'-methoxyflavone. The research results of antimicrobial activity are shown in table. 1 and 2.

Determination of acute toxicity and calculations LD50carried out according to the method of Cerberus [4] White mice weighing 20 g were injected intraperitoneally 0.5 ml of aqueous suspensions of the compounds. The suspension was prepared in Tween-80, at each dose in the experience took 6 mice.

The results of these studies show that the claimed compound has a pronounced antimicrobial action, exceeding the activity norsulfazola (similar action) and 7 - hydroxy-6-bromo-4'-methoxyflavone (similar in structure and action).

The claimed compound does not affect the growth of microorganisms of the intestinal-typeslogo family.

This indicates the feasibility of further studies of this compound with the aim of creating effective drug.

7-Acetoxy-6-bromo-3-formylchromones formula

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have an antimicrobial effect against Staphylococcus and spore flora that do not affect intestinal flora.

 

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