CS215487B1 - N,n,-bis+l alkymethyl+p-1,2-etandiamindioxides and method of preparation thereof - Google Patents

Abstract

The present invention relates to N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides formula 9 9 R - N - CH2 - CH2 - N - R OH CH 5 3 wherein R is 8 to 14 carbon atoms in the alkyl chain and method for preparing these compounds from N, N'- bis (alkylmethyl) -1,2-ethanediamines by aqueous oxidation hydrogen peroxide solution. Finally, the compounds have a pronounced antimicrobial effect as well as surface-active properties.

Description

The invention relates to N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides of the general formula

R - N - CH - CH - N - R ₍ 2 R,

CH ₅ CH ₅ wherein R is an alkyl chain having a carbon number 8 to 14.

In terms of antimicrobial activity, non-aromatic amine oxides which contain at least one long alkyl chain in their molecule are among the active compounds. In addition to their biological activity, they also have surface-active properties.

Hitherto known amine oxides are derived from 1,2-ethanediamine of the Ν, Ν'-bisdialkyl type wherein the alkyl chain contains 1 or 2 carbon atoms. However, these compounds are ineffective as well as antimicrobial and surface active.

The compounds of the invention are novel substances which have not been previously described in the chemical literature and have been found to have unknown effects on microorganisms.

The examples show selected compounds of the invention and methods for their preparation as well as their characterization together with an indication of their antimicrobial activity (given as the minimum

Claims (2)

SUBJECT N, N'-bis (alkylmethyl) -1,2-ethanediamine dioxides of the general formula 0 0 B - C - CHG - CHG - N - R ₃ H CH ₃ wherein R is an alkyl chain containing 8 to 14 carbon atoms. 2. A method for the preparation of compounds of general formula 21487 inhibitory concentration - MIC - in pg / ml on Staphylococcus aureus, Escherichia coli and Candida albicans strains). Example 1 0.1 mol of N, N'-bis (methylnonyl) -1,2-ethanediamine is dissolved in methanol and 0.3 mol of 20-30% aqueous hydrogen peroxide solution is added at 40-50 ° C. The mixture was allowed to react for 4 hours at 60-70 ° C. After cooling, the excess hydrogen peroxide is decomposed, the solvent and water are evaporated, and the dry residue is recrystallized from dry acetone. This gives N, N'-bis (methylnonyl) -1,2-ethanediamine dioxide having a melting point of 128-130 ° C; _Rt = 0.85 (Silufol, system acetone-1N HC1 (1: 1), detection Dragendorfovým agent); yield 84% of theory; MIC 50; 200; 90; IR spectra: at _NO : 939 and 947 cm ^-1 (nujol). Example 2 The procedure and the batches were identical to those described in Example 1, using N, N'-bis (methyltridecyl) -1,2-ethanediamine in the reaction. The product N, N'-bis (methyltridecyl) -1,2-ethanediamine dioxide has mp 107-110 ° C; Rf = 0.45; yield 84% of theory; MIC 70; 800; 70; IR spectrum: at _NO : 918 and 936 cm @ ^-1 (nujol). All compounds of the invention were identified by elemental analysis and spectral methods. OF THE INVENTION ca as in point 1, characterized in that ´ N, N'-bis (alkylmethyl) -1,2-ethanediamine of the general formula is oxidized R - N - CH - CH - N - R I I CH, CH, wherein R is as defined in 1.20 to 30% aqueous hydrogen peroxide at temperatures of 40 to 70 ° C.