Antimicrobial Activity of N-Alkoxycarbonylmethyl-N-alkyl-piperidinium Chlorides

Abstract

The aim of the study was to assay antibacterial and antifungal activity of newly synthesised N-alkoxycarbonylmethyl-N-alkyl-piperidinium chlorides. The compounds tested were found to inhibit the growth of some Gram-negative bacteria, Gram-positive strains and some representatives of yeast-type Candida. From microbiological experiments two of the compounds tested, N-dodecyloxycarbonylmethyl-N-methyl-piperidinium chloride (3) and N-dodecyl-Nethoxycarbonylmethyl-piperidinium chloride (6), emerged as more active than the other compounds. Since the resistance of biofilms to biocides should be noted during the design and testing of new antimicrobial agents therefore, we have analysed antibacterial properties of the most active compounds towards biofilms. Our study focused on strains of Pseudomonas aeruginosa and Staphylococcus aureus that served as main model organisms for the biofilm studies.

Synthesis and Antimicrobial Activities of some Quaternary Morpholinium Chlorides

“…Their activity has been related to the structure, type of substituents and anions (Shelton et al, 1946). Recently, we have synthesized N-carboxymethyl-Nalkyl-piperidinium chlorides and N-carbalkoxymethyl-4-hydroxy-N-methyl-piperidinium chlorides, and tested them against some bacteria, yeast and fungi (Woniak et al, 2004;Dega-Szafran et al, 2007). The promising pharmacological properties of this type of salts have prompted the synthesis of a series of morpholinium salts with N-alkyl, N-carboxyalkyl and N-carbalkoxymethyl groups attached to the nitrogen atom, of alkyl groups in a range of C 1 -C 16 carbon atoms (Table I), to obtain more information on the effects of the structure and the alkyl chain on their biocidal activities against bacteria: Staphylococcus aureus, Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa and fungi: Candida albicans and Trichophyton menthagrophytes.…”

On the Head Group Effect on Critical Micelle Concentration of Cationic Surfactants Using Molecular Connectivity Indices and Atomic Partial Charges

“…As follows from Table 3, the highest values of the correlation coefficients in the third step are for the relationships containing the 0 , 0 , and 3 c indices and also for 0 , 0 , and 3 c . Because the 3 c , 3 c indices highly correlate ( r = 0.997), and also the 3 c index encodes only information about the number of branches and their environment while the 3 c index additionally encodes the information about heteroatoms, i.e., the relationship which contains the 3 c index is richer in structural information [29], thus the relationship which contains the 3 c index will be ignored in further considerations.…”

“…All the molecular connectivity indices were calculated based on the hydrogen-suppressed graphic structural formula of the molecule. The values of the 0 and 0 indices increase when the number of atoms in the head group increases but the values of the 3 c index increase with the increase number of branches in the head group. The analysis of the variation of the values of nitrogen charges ( Q N + ) in Table 2 shows that the charge localized on the quaternary nitrogen atom increases with the increase of size caused by elongation of the hydrocarbon chains (compounds 2-4), or it decreases with the increase of the number of -CH 2 CH 2 OCH 3 groups in the head group (compounds [13][14][15].…”

“…Cationic surfactants have attracted the attention of chemists for a long time due to their wide application in various fields of industry and medicine. Their utility results from, among other things, their antimicrobial activities [1][2][3] and anticorrosion properties [4,5]. The medical applications of cationic surfactants include their use as antimicrobial agents, as drug delivery agents and also as gene delivery agents.…”

Synthesis and characterization of 1-carbalkoxymethyl-4-hydroxy-1-methylpiperidinium chlorides

“…4 The most active are Ncarbdodecyloxymethyl-N-methylpiperidinium chloride and N-carbethoxymethyl-Ndodecylpiperidinium chloride, whose activity is greater than that of dodecyl-trimethylammonium chloride, usually used as a reference substance in the microbiological tests. The promising pharmacological properties of this type of salts have prompted a synthesis of a series of piperidinium salts in which the hydroxyl group is at the piperidinium ring.…”