SU1089935A1 - 3-(benzyloxymethyl-3-[4-methoxyphenyl]-4-(3n)-quinozolone displaying antimicrobal activity - Google Patents

Abstract

2-Benzyloxymethyl-3-

Description

filter 300 ml of water, crystallized from ethanol; Needles with mp 136-137 0. Yield 48.7%. .

Found.,%: C, 63.81; H, 4.32; N 9.42 C1 11.75. ,; - ,, Cl% 02.

Calculated,%: C 63.90; H 4.35, N 9.31; Cl.11.78.

IR spectrum, cm (petroleum jelly maelo): 1688 (); 1645, 1615, 1480. (quinazolone bands).

Example 2: Preparation of 2-benzyloxymethyl-3- (4-methoxy-feiyl) -4 (3H) -quinazolbna.

A solution of 3.0 g (0.01 mol) of 2-chloromethyl-3- (4-methoxyphenyl) -4 (ZN) -quinazolone in 10 ml. methanol is poured into a solution of sodium benzyl obtained from 0.23 g (0.01 g-at) of metallic sodium and 3 ml of benzyl alcohol, then the reaction mixture is heated with 4 4 j methanol and distilled off, after cooling, the precipitated precipitate is filtered off and crystallized from ethanol. Needles with so pl. 28-131 ° C. Yield 55%. . Found,%: C 74.22; H 5.40, N-7.7

Calculated,%: € 74,17; H 5.41;

.N 7.52.

IR spectrum, cm (liquid paraffin): 1690; 1600; 1515; I482i 1290.

To determine the bacteriostatic activity, the test substance was dissolved in ethyl alcohol at a ratio of 1: 100 and diluted with mopotone broth (MPB) to a ratio of 1: 500.

Bacteriostatic activity was studied by the method of successive dilutions of the resulting solution in MPV with respect to the reference strains of Staphylococcus aureus (gram-positive bacteria) and Escherichia coli (gram-negative bacteria). A daily culture that was grown on m-septon agar was used with a sterile physiological solution of sodium chloride and the initial dilution was prepared with concentration; 500 million microbial cells per 1 ml of rinse were prepared according to the bacterial standard. The resulting mixture was diluted with sterile syringes, 100 times. This dilution of the bacterial culture with a concentration of 5 million microbial cells in 1 MP and was a working solution. The latter in the amount of 0 ml was added to 2 ml of syringes containing the corresponding dilution of the test substance. Thus, the bacterial load per 1 ml of fluid is 250,000 microbial cells. The results of the experiments took into account, after 18–20 h, the overruns of the control and test tubes in the thermostat at 36–37. The presence of bacterial cultures or the absence of bacterial cultures was recorded. The minimum inhibitory concentration of the drug in μg / ml, which retarded the growth of bacterial cultures, was taken as the active dose.

The acute toxicity of the compound was determined by a single dose of increasing doses, causing death from 0 to 100% of the animals. The compound was administered intraperitoneally in starch mucus. For each dose, 6 mice weighing 1620 g were taken into the experiment. The observation was carried out for 10 days with daily registration of the death of animals. The study was conducted on 36 minutes.

The results of the experiment were processed statistically by the method of Litchfield and Wilcoxon at p 0.05.

The average lethal dose of a wound is 740 (700-782) Mf / kg.

The results of studies of the antimicrobial activity of 2-benzshloxymethyl-3- (4-methoxyphenyl) -4 (3N) -hinzolone are presented in the table.

Thus, the compound of formula I has a high antimicrobial activity against the reference strain of Staphylococcus aureus 209-P at a concentration of 62 μg / ml, as can be seen from the table, compound I is 8 times higher than the antimicrobial activity of the analogue in the structure of 2-ethyl-3-benzylideneamine -4 (3N) -quinazolone. and can be used in medicine.

Have

, V% - Q-OCH3

G CH2-OCH2SbN5

62

500

62

500

500

500

Claims (1)

2-Benzyloxymethyl-3- (4-methoxyphenyl) -4 (3N) -quinazolone of formula I about Igoozy ₃ C11 ₂ -0CH ₂ C ₆ 11 ₅ exhibiting antimicrobial activity. . •