2-hydroxy-1-naphthylethylenediamine 5-nitro-2-furaldehyde exhibiting antimicrobial activity against the bacteria of the genus staphylococcus


(57) Abstract:

Usage: in medicine, as an antimicrobial agent to bacteria Staphlyococcus. The inventive product 2-hydroxy-1-naphthylethylene 5-nitro-2-furaldehyde. B. F. C16H11N3O4. Tpl.200 201°C (with decomp. ) LD50more than 1000 mg/kg the Minimum inhibitory concentration of 0.07 to 1.25 μg/ml Minimum bactericidal design of 0.07 to 1.25 µg/ml, which is several times the action furazolidone. Reagent 1: hydrazone 2-hydroxy-1-naphthaldehyde. Reagent 2: 5-nitrofurfural. Process conditions: in the midst of ethanol at 50°C. table 1.

The invention relates to new biologically active compounds, namely 2-hydroxy-1-naphthylethylenediamine 5-nitro-2-furaldehyde exhibiting antimicrobial activity against the bacteria of the genus Stapylococcus and which may find application in medical practice as an antimicrobial drug.

In medical practice for the treatment of infections caused by gram-positive and gram-negative microorganisms used furazolidone (N-(5-nitro-2-furfurylamine)-3-aminooxy - soliton-2) formula

-N= CHNO2He belongs to the class of low-toxic substances (LD501758 mg/to the BR> However, in cases when you want more high activity and low toxicity of antimicrobial drug, it can not be used.

The present invention proposes a new substance: 2-hydroxy-1-naphthylethylenediamine 5-nitro-2-furaldehyde exhibiting antimicrobial activity against bacteria of the genus Staphylococcus.

The technical result of the invention is to find new substances with high antimicrobial activity against bacteria of the genus Staphylococcus and is achieved through the synthesis of the compounds of formula

This antimicrobial activity against bacteria of the genus Staphylococcus synthetic substances increases in 1,3-93 times in comparison with the practice furazolidone.

Comparative analysis of the prototype shows that the claimed compound is characterized by the fact that it is a fragment of the 3-aminoquinoline-2 replaced by 2-hydroxy-1-naphthylethylenediamine.

The compound obtained by condensation reaction of hydrazone 2-hydroxy-1-naphthaldehyde with 5-nitrofurfural taken in the ratio of 1:1 for 10-15 minutes according to the following reaction

< / BR>
The method of obtaining the claimed matter is simple in execution, the original prophetic is dimetilformamide and dimethyl sulfoxide, little soluble in aliphatic alcohols, acetone, water, practically insoluble in ether.

An example of obtaining 2-hydroxy-1-naphthylethylenediamine 5-nitro-2-furaldehyde (number of state registration 10065890 from 21.11.90).

To a hot ( 50about(C) ethanol solution of 1.86 g (10 mmol) of hydrazone 2-hydroxy-1-naphthaldehyde in 70 ml of ethanol is poured a solution of 1.41 g (10 mmol) 5-nitrofurfural in 30 ml2H2HE. Almost immediately formed a yellow-orange precipitate. The reaction mixture is cooled to room temperature, the resulting material is filtered off, washed it with ethanol, ether and dried in air. The output of 2.72 g, which is 88% of theoretically calculated; TPL200-201aboutC (with decomp.).

Found, With 62,01, 59,94; N 3,40, 3,51; N 13,50, 13,69.

Calculated With 62,14; N. Of 3.56; N 13,59.

the data of IR spectroscopy, cm-1: (HE) 3450; (CH) furan 3160; (CH) 2920 cm-1; (C=N) 1630; (C=C), 1590;as(NO2) 1510, 1340; (C-O) 1320; (HE) 1240; (C-O-C) furan 1240, 1220; (C-N) 1185, 1110; and (C-N) 970, 925.

Study of antimicrobial activity of compounds was carried out using twofold serial dilutions [2] in the liquid nutrient medium (meat-peptone broth, pH 7.0). Vesiculosa.

The tests were carried out with cultures of Staphylococcus aureus (strains Wood-46, Cowan-1, Smith, 209 (H) and Staphylococcus epidermidis (42-a). For seeding used the 18-hour agar culture of these microorganisms. Sowing dose 250-500 thousand microbial cells in 1 ml of medium (optical standard turbidity). The tubes were shaken and placed in a thermostat at 243 h at 37aboutC, control served as a nutrient medium with a culture without the test chemical compound. Bacteriostatic activity was determined by the lack of growth in a nutrient medium, and bactericidal by re-seeding from tubes with no visible growth and incubation.

Toxicity tests conducted in acute experiments on white mice by introducing into the stomach of suspended matter in boiled water.

The results are presented in the table in comparison with antimicrobial activity used in medical practice furazolidone, a structural analogue of the claimed substance and having the highest activity among antimicrobials nitrofuranovye type.

As can be seen from the table, the claimed compound exhibits high as bacteriostatic and bactericidal activity to all ispytannaya about what bacteriostatic activity it 1.3 93 times that of structural analogues. Toxicity also declare the connection as well as furazolidone can be classified as low-toxic substances.

Detected properties of the synthesized compounds are of interest from the point of view of the backup extension antimicrobial agents.

2-Hydroxy-1-naphthylethylenediamine 5-nitro-2-furaldehyde formula

showing antimicrobial activity against the bacteria of the genus Staphylococcus


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