SU1515636A1 - 1-phenyl-5-(2-hydroxy-5-chlorophenyl)-pentadiend-1,3-oh-5 possessing antimicrobial activity - Google Patents

Description

The invention relates to organic chemistry and relates, in particular, to the novel vinyllog of chalcone 1-phenyl 5- (2ggilroxy 5-chlorophenyl) penta) 1.3); she is g-5 of formula I,

HE

..- V CH-CH CH- (O)

f ° i. n with antimicrobial activity against spore-forming microflora.

 The invention is a compound discovery that has the highest antimicrobial activity against spore-aeration and microorganisms with improved properties and lower toxicity.

EXAMPLE 1. g (0.02 mol) of 2-gilroxy-: 5-chloroacetophenone and 2.51 ml (0.02 mol) of cinnamic aldehyde are dissolved in 30 ml of ethanol and added with vigorous stirring sodium hydroxide solution containing g of NaOH in 6 ml of water. Stirring is continued for 3 m, after which the reaction mixture is left for 10 hours, then 50 g of crushed ice is added to the reaction mixture and acidified with HCl hydrochloric acid to pH So The precipitated precipitate is filtered, washed with water until neutral and dried to constant weight. Output I B. g g (33,). Crystallized from a mixture of chloroform - petroleum ether, So pl. 1 49 ° C.

SP

ate

ABOUT)

00

3

71.81;

H "4.56;

151

477;

265 MM

Found%: C C1 12.39. C,., H, C10 ,.

Calculated,%: C, 71.70; H C1 P, b.

In the UV spectrum: d, im, (in ethanol).

In the IR spectrum: 3200-2700 (OH); 1635 cm-); 1600 cm (). The study of the antibacterial activity of the obtained compound I was performed by the method of twofold serial dilutions (from 10 to 320 µg / ml) in nutrient agar). Dimethyl sulfoxide is used to dissolve. Similar nutrient media are used as controls, containing no solvent and containing the solvent in the greatest amount used in each experiment, but not affecting the viability of the test cultures. Norsulfazole is used as an analog in action,

The experiment included staphylococci, spore-forming bacteria, and representatives of the intestinal-typhoid group.

The hundred millionth suspension of the daily agar culture of each strain is seeded with a bacteriological loop through sectors of Petri dishes with nutrient media containing increasing amounts of the test substance. Similarly, make crops on the control environment. The results of each experiment are taken into account after the “bhour hours incubation of crops in the thermostat at.

Researches show that 1gfeg-5- (2thydroxy-5-chlorophenyl) pentadiene 1, 3 oH5i5 has a high antibacterial effect, 10 times more than norsulfazole, selectively inhibits the growth of spore-forming bacteria at a concentration of 30-DO µg / ml or more.

Only at a concentration of 320 µg / ml. this compound has a detrimental effect on staphylococci and has absolutely no effect on the representatives of the intestinal typhoid group at concentrations of 320 µg / ml and below. The results are shown in the table.

Acute toxicity is determined according to Kerber in white mice when administered orally. It was established that for the claimed compound LD5 is 500 mg / kg, which is 2.5 times lower than that of the structural analogue — 1-phenyl 1.5 g (2, P-C5 bromophenyl) g pentadien; 1,3-she-5 of formula II

BUT

for which LD is 200 mg / kg.

Thus, 17phenip55- (2 hydroxy-5-chlorophenyl) lenadien 1, selectively interferes with the growth and reproduction of spore-forming bacteria and exceeds the effect of structural analogue II and analogue by the action (norsulfazole) by n times, and is also less toxic.

Claims (1)

Invention Formula 1 gphenyl "5 (2hydroxy: 3 h (lorofenyl) pentadiene 1, formula HE / -, f CH-CH "CH- (O) about having antimicrobial activity against spore-forming microflora.