CS277214B6 - Ν, Ν-Dialkylmonoazoniumrownhalides and their preparation - Google Patents

Abstract

The solution relates to antimicrobially active amphiphilic monoazacrownethers of the type Ν,Ν-dialkylmonoazoniumcrownhalides where R represents a hydrocarbon chain with a number of carbon atoms of 8 to 16, R' represents methyl or ethyl, n represents 3 or 4, X = Br or Cl and a method of their preparation, which involves the reaction of the N-alkylated monoazacrownether with the corresponding bromine or a chloroalkane at temperatures of 20 to 24 hours. The compounds mentioned are also organic solvents, have a broad-spectrum antimicrobial effect and are therefore usable as multifunctional compounds, especially as detergents with simultaneous disinfection and chelation effects wherever it is expedient to combine solubilizing, detergent, complexing properties and antimicrobial effects, for example also for the capture of some (including radioactive) elements from industrial waters.

Description

1 CS 277214 B6

The invention of sacrownethers of the formula refers to the antimicrobically active amphiphilic monoaza-N, N-dialkylmonoazonium cyclohalides in general.

wherein R is a linear hydrocarbon chain having a carbon number of "k 8 to 16, R is methyl or ethyl, n = 3 or 4 and X = Br or Cl and the method for their preparation.

Macrocyclic compounds represent a group of substances capable of selectively forming complexes with metal ions, possibly anionic compounds, and thus can serve as a model of the current concept of "key lock". One of their disadvantages, especially long-chain derivatives, is their minimal solubility in water. Therefore, new groups of water-soluble macrocycles are searched with precisely defined hydrophobic and hydrophilic structural elements. Organic ammonium salts in combination with lipophilic long chains are suitable for such compounds. Macrocyclic ammonium salts are known (Schmidtchen FP, Chem. Ber. 117, 1287 (1984) and literature cited there; Petti. H. et al. J. Am. Chem. Soc. 110, 6825 (1988); J. Org., Chem., 53, 5964 (1988), but which contain a long alkyl moiety in their molecule. There is also no known data on the antimicrobial activity of simple amphiphilic crown ether types of ammonium salts.

The compounds of the present invention are novel, not previously described in the chemical literature, and have found effects on various types of microorganisms. The process for their preparation consists in the reaction of the corresponding N-alkyl monoazacrowethane with 1-haloalkane in the absence, solvent and solvent. EXAMPLE 1 6.23 g (0.025 mol) of 1-bromododecane are added to 5.48 g (0.025 mol) of N-methyl monoazoate and 15-crown-5-ether and reacted at 20 DEG C. for 12 hours. Dry ethanol is then added and the reaction mixture is heated to reflux for 12 hours. After the solvent is distilled off, the product is dried by azeotropic distillation with ether and recrystallized to give a white, waxy hygroscopic N-dodecyl-N-methylmonoazonium-15-crown-5-bromide. in 82% of theory; mp 64-65 ° C; IR (cm < -1 >, paraffin oil suspension, KBr) COC 1124 valence vibration band; 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, CS 277214 B6 2

N, 2.90 / 2.93. Antimicrobial activity (minimum inhibitory concentration of MIC in mol / dm 3 x 10 4) S. aureus 0.12, E. coli 4.97, C.albicans 3.73. Example 2

1-bromooctane was used in the working procedure 1 with the difference that the oily one was very similar to that described in the example reaction. Obtained isotropic N-octyl-N-methylmonoazonium 15-crown-5-bromide in 76% yield; IR COC 1121 cm @ -1. Elemental analysis for C19 H40 BrNO4 (calculated / 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) of S. aureus 0.70, E. coli 23.45, C. albicans8.76. Example 3

The working procedure is the same as in Example 1 except that 1-chlorohexadecane was used in the reaction. A white, waxy, slightly hygroscopic N-hexadecyl-N-methylmonoazonium 15-crown-5-chloride was obtained in 45% yield; IR COC 1127 cm -1. Elemental analysis for C 27 H 56 ClNO 4 calculated / 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.