CS277214B6 - N,n-dialkylmonoazoniumcrownhalides and process for preparing thereof - Google Patents

Abstract

The solution relates to antimicrobically effective amphiphilic monoazacrownester type Ν, Ν-dialkylmonoazoniumcrownhalides where R represents a hydrocarbon chain of carbon atoms of 8 to 16, R 'is methyl or ethyl, n is 3 or 4, X = Br or Cl and a process for their preparation which is alkylated monopríslušným bromine or temperatures of 20 to in the reaction azacrownéteru s chloroalkane at within 24 hours The compounds are organic solvents, they have broad-spectrum antimicrobial effect and are therefore useful as multifunctional compounds as detergents with the present disinfectant and chelating effect wherever there is a need to combine solubilization, detergent, complexing properties and antimicrobial effect, for example also for the uptake of some (even radioactive) elements of industrial waters.

Description

The present invention relates to antimicrobially active amphiphilic monoases of N, N-dialkylmonoazonium chromium halides of the general formula

wherein R represents a linear hydrocarbon chain having 8 to 16 carbon atoms, R represents methyl or ethyl, n = 3 or 4 and X = Br or Cl and a process for their preparation.

Macrocyclic compounds represent a group of substances capable of selectively forming complexes with metal ions or anionic compounds and can thus serve as a model for the current concept of lock and key. One of their disadvantages, especially of long chain derivatives, is their minimal solubility in water. Therefore, new groups of water-soluble macrocycles with precisely defined hydrophobic and hydrophilic structural elements are being sought. Organic ammonium salts in combination with lipophilic long chains are suitable candidates for this type of compound.

Macrocyclic ammonium salts are known (Schmidtchen FP, Chem. Ber. 117, 1287 (1984) and literature cited therein; Petti A. H. et al. J. Am. Chem. Soc. 110, 6825 (1988); Ikeda et al. J. Org. Chem. 53, 5964 (1988)), which, however, do not contain a long alkyl radical in their molecule. There are also no known data on the antimicrobial activity of simple amphiphilic ammonium salt type crowthers.

The compounds which are the subject of the invention are new substances which have not been described in the chemical literature and have hitherto been found to have unknown effects on various types of microorganisms. The process for their preparation consists in the reaction of the corresponding N-alkylmonoazacernate with a 1-haloalkane in the absence of a solvent and in a solvent. '

Example 1

To 5.48 g (0.025 mol) of N-methylmonoase 15-crown-5-ether was added 6.23 g (0.025 mol) of 1-bromododecane and allowed to react for 12 hours at 20 ° C. Dry ethanol is then added and the reaction mixture is heated under reflux for 12 hours. bromide in 82% yield; mp 64-65 ° C; IR (cm ^-1 , paraffin oil suspension, KBr) valence vibration band COC 1124; ¹ H NMR chemical shift (ppm, CDCl 3, TMS) 0.81 (t, CH 3), 3.50-3.59 (m, 6xCH 2), 1.06-2.00 (m, 8xCH 2) 1.46- 2.00 (m, CH 2), 3.29 (s, CH 3) 3.77-4.13 (m, 6xCH 2 adjacent to N ⁺ ). Elemental analysis for C 23 H ₄₈ BrNO ₄ (C, H, N in%, calculated / found) C 57.25 / 57.59, H 10.03 / 10.17,

N 2.90 / 2.93. Antimicrobial activity (minimum inhibitory concentration MIC in mol / dm ³ x 10 ⁴ ) S. aureus 0.12, E. coli 4.97, C. albicans 3.73.

Example 2

The procedure is the same as in Example 1, except that 1-bromooctane is used in the reaction. An oily, highly hygroscopic N-octyl-N-methylmonoazonium 15-crown-5-bromide is obtained in a yield of 76% of theory; IR COC 1121 cm “ ¹ . Elemental analysis for C ₄₀ H _ig BrNO ₄ (calcd / found) C 53.52 / 53.21 H 9.46 / 9.82, N 3.29 / 3.06. Antimicrobial activity (MIC in mol / dm ³ x 10 ⁴ ) S. aureus 0.70, E. coli 23.45, C. albicans 8.76.

Example 3

The procedure is the same as in Example 1, except that 1-chlorohexadecane is used in the reaction. White, waxy, slightly hygroscopic N-hexadecyl-N-methylmonoazonium 15-crown-5-chloride is obtained in a yield of 45% of theory; IR COC 1127 cm- ¹ . Elemental analysis for C 7 ^H 56 ₂ 4 ^C1NO calcd / found) C, 65.62 / 65.44; H, 11.42 / 11.59, N 2.84 / 2.76. Antimicrobial activity (MIC in mol / dm ³ x 10 ⁴ ) S. aureus 0.61, E. coli 14.17, C. albicans 8.10.

Claims (2)

PATENT CLAIMS 1. Ν, Ν-Dialkylmonoazonium chromium halides of the general formula wherein R is a hydrocarbon chain having 8 to 16 carbon atoms, R 'is methyl or ethyl, n is 3 or 4 and X is Br or Cl. 2. A process for the preparation of compounds of the general formula according to item 1, characterized in that an N-alkylmonoazacroether of the formula 'is reacted. wherein Ran is the same as in point 1 with halomethane or haloethane, where halogen is chlorine or bromine, or the N-alkylmonoazacernate of the above formula is reacted wherein R is methyl or ethyl and n is the same as in point 1 with 1-bromo- or a 1-chloroalkane containing 8 to 16 carbon atoms in the chain at temperatures of 20 to 80 ° C for 24 hours without or in the presence of a solvent.