RU1817775C - 2,4,6-trimethyl-3-nitrobenzenesulfochloride as antiseptic agent - Google Patents

Abstract

Usage: as an antiseptic. SUMMARY OF THE INVENTION: The product is 2,4,6-trimethyl-3-nitrobenzene-sulfochloride, 2,4,6- (CH3) s-3-M02-C6HS02CI. BF Cd Nu CI N04 S. yield 26.6%, mp 60 to 61 ° C. Reagent 1: chlorosulfonic acid. Reagent 2: nitromesitylene. Reaction conditions: in chloroform at 35 ° C. 2 tab. (L With a meter, a vent pipe and a dropping funnel, 26.8 g (0.23 mol) of chlorosulfonic acid HOS02CI are placed, then, with vigorous stirring and room temperature, 16.5 g (0.1 mol) of nitromesitylene CgHnNOz are pinned, dissolved in 60 g of chloroform, the flask is cooled in a water bath, without allowing the temperature to rise above 35 ° C. After the completion of the pinning of the nitromesitylene solution, the mixture is stirred for another 30 minutes and the reaction product is poured into a 1-liter flask containing 0.2 kg finely divided ice with thorough mixing ii.-At the end of decomposition 00 and VJ VI trunk GJ

Description

of acid residues, all ice melts, and at the bottom of the vessel a thick mass of CHCO and sulfochloride is formed. After separation of the water, hexane-benzene (1; 1) was added to the residue, and after the precipitate had been completely dissolved, it was dried over CaCl2 for 12 hours. The solvent was distilled off, the product was isolated, which was then recrystallized from hexane. Yield g (0.03 M) or 26.6%.

The antibacterial properties of 2,4,6-trimethyl-3-nitrobenzenesulfonyl chloride were detected by determining the sensitivity of microbes to the specified preparation by the method using the serial dilution method in a liquid nutrient medium. The values of the minimum inhibiting growth of microbes with a concentration of 2,4,6-trimethyl-3-nitrobenzenesulfonyl loride are equal to: with respect to Ps. aeruginosa 8 μg / ml; in relation to Salm. typh 16 μg / ml; in relation to Staph. aureus and E. coli 128 μg / ml.

It is known that active antimicrobial agents of similar structure used in medicine include:

- phosphonium sulfamides of the general formula Ph3PCH CHC (R) NP1} CI (see table. 1)

-depo-sulfonylamide preparations - table 2.

As can be seen from the above data, the resulting preparation is very effective against Ps. aeruginosa (8 μg / ml) and Salm. typhi (16 μg / ml) and has good efficacy against Staph. aereus and E. col (128 µg / ml), which gives it a significant advantage over the aforementioned sulfanilamide preparations, some of which are widely used in medicine.

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The toxicity of the proposed drug has not been investigated. However, based on the fact that the values of the minimum microbial growth inhibiting concentrations of 2,4,6-trimethyl-3-nitrobenzenesulfonyl chloride are on the threshold of sensitivity of the method used (especially with respect to Ps. Aeruginosa and Salm. Typhi), non-toxicity can be suggested this compound within the concentration used. In addition, structurally similar compounds (chloramines B, T, CB) are widely used in medical practice.

Thus, the data obtained as a result of laboratory studies of the antibacterial activity of 2,4,6-trimethyl-3-nitrobenzenesulfrnyl chloride indicate:

2,4,6-trimethyl-3-nitrobenzenesulfonylyl chloride is an inhibitor of the growth of the following bacterial species: Staph. aereus. E. coll, Salm. typhi, Ps. aeruginosa.

Especially pronounced biological activity against gram-negative microbes (Salm. Typhi and Ps. Aeruginosa) was noted.

. The studied drug can be used as an antiseptic.

Claims (1)

The claims 2,4,6-Trimethyl-3-nitrobenzenesulfochloride of the formula 35 40 as an antiseptic. Table 1 A drug Sulfazine (sulfadiazine. 2-sulfanilamidopyrimidine) Sulphometoxazole. (ha nta nol, 3-sulfanilamido-5-methyl-isoxazole). Sulfadimethoxin (madribon. 6-sulfanilamido-2.4-dimethoxypyrimidine) Continuation of the table. 1 table 2 Antimicrobial activity, mcg / ml Ps. aeruglnosa E. coli 26 1000 25 195 2000