53657-08-2Relevant articles and documents
Inhibition of bacterial growth and galactosyltransferase activity of WbwC by α, ω-bis(3-alkyl-1H-imidazolium)alkane salts: Effect of varying carbon content
Brockhausen, Inka,Kocev, Alexander,Kong, Xianqi,Melamed, Jacob,Szarek, Walter A.,Vlahakis, Jason Z.,Wang, Shuo,Xu, Yaozu
, (2020/04/21)
A series of compounds was designed and synthesized having two imidazolium rings separated by a polymethylene spacer and having alkyl substituents on each of the imidazolium rings. The compounds were assayed for their effects on the activity of galactosyltransferase WbwC, and also on the growth of Gram-negative and Gram-positive bacteria, as well as human cells. The inhibition observed on enzyme activities and cell growth was dependent on the total number of carbons in the spacer and the alkyl substituents on the imidazolium rings. These readily synthesized, achiral compounds have potential as antimicrobial and antiseptic agents.
Liquid Nickel Salts: Synthesis, Crystal Structure Determination, and Electrochemical Synthesis of Nickel Nanoparticles
Sniekers, Jeroen,Verguts, Ken,Brooks, Neil R.,Schaltin, Stijn,Phan, Thanh Hai,Trung Huynh, Thi Mien,Van Meervelt, Luc,Defeyter, Steven,Seo, Jin Won,Fransaer, Jan,Binnemans, Koen
, p. 1010 - 1020 (2016/01/16)
New nickel-containing ionic liquids were synthesized, characterized and their electrochemistry was investigated. In addition, a mechanism for the electrochemical synthesis of nanoparticles from these compounds is proposed. In these so-called liquid metal salts, the nickel(II) cation is octahedrally coordinated by six N-alkylimidazole ligands. The different counter anions that were used are bis(trifluoromethanesulfonyl)imide (Tf2N-), trifluoromethanesulfonate (OTf-) and methanesulfonate (OMs-). Several different N-alkylimidazoles were considered, with the alkyl sidechain ranging in length from methyl to dodecyl. The newly synthesized liquid metal salts were characterized by CHN analysis, FTIR, DSC, TGA and viscosity measurements. An odd-even effect was observed for the melting temperatures and viscosities of the ionic liquids, with the complexes with an even number of carbon atoms in the alkyl chain of the imidazole having a higher melting temperature and a lower viscosity than the complexes with an odd number of carbons. The crystal structures of several of the nickel(II) complexes that are not liquid at room temperature were determined. The electrochemistry of the compounds with the lowest viscosities was investigated. The nickel(II) cation could be reduced but surprisingly no nickel deposits were obtained on the electrode. Instead, nickel nanoparticles were formed at 100 % selectivity, as confirmed by TEM. The magnetic properties of these nanoparticles were investigated by SQUID measurements.
Concentration and temperature induced dual-responsive wormlike micelle to hydrogel transition in ionic liquid-type surfactant [C16imC9]Br aqueous solution without additives
Hu, Yimin,Ge, Lingling,Han, Jie,Guo, Rong
, p. 5624 - 5631 (2015/07/20)
A highly viscoelastic fluid formed by the ionic liquid-type surfactant 1-hexadecyl-3-nonyl imidazolium bromide ([C16imC9]Br) in water in the absence of any additive was studied. The phase behavior and morphology of aggregates were studied by a combination of rheological techniques, small-angle X-ray scattering (SAXS), cryo-etch-scanning electron microscopy (cryo-etch-SEM) and freeze-fractured transmission electron microscopy (FF-TEM). [C16imC9]Br aqueous solutions showed interesting rheological behavior as a function of both concentration and temperature, which invoked a transition between wormlike micelles and hydrogels. With the increase in [C16imC9]Br concentration, the aqueous solution could form viscoelastic wormlike micelles (50-80 mM), hydrogels (90-110 mM) and wormlike micelles (120-180 mM). As the temperature increased, the hydrogels (90-110 mM) could also transit to wormlike micelles. The unusual phase transition between wormlike micelles and elastic hydrogels was postulated to be the change of the average micellar length.
Antimicrobial activity and SAR study of new gemini imidazolium-based chlorides
Pa?kowski, ?ukasz,B?aszczyński, Jerzy,Skrzypczak, Andrzej,B?aszczak, Jan,Kozakowska, Karolina,Wróblewska, Joanna,Kozuszko, Sylwia,Gospodarek, Eugenia,Krysiński, Jerzy,S?owiński, Roman
, p. 278 - 288 (2014/03/21)
A series of 70 new 3,3′(α,ω-dioxaalkyl)bis(1- alkylimidazolium) chlorides were synthesized. They were characterized with respect to surface active properties and antimicrobial activity against the following pathogens: Staphylococcus aureus, Enterococcus faecalis, Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Pseudomonas aeruginosa, Candida krusei, and Candida albicans. In this article, besides description of the synthesis, we characterize a set of features of these compounds, concerning their structure (described by the length of the dioxaalkan spacer and the length of the alkyl substituent in the aromatic ring) and surface active properties (critical micelle concentration, value of surface tension at critical micelle concentration, value of surface excess, molecular area of a single particle, and free energy of adsorption of molecule). Then, we present a SAR study for Staphylococcus aureus, as one of the most widespread pathogenic strains, conducted with the help of the Dominance-based Rough Set Approach (DRSA), that involves identification of relevant features and relevant combinations of features being in strong relationship with a high antimicrobial activity of the compounds. The SAR study shows, moreover, that the antimicrobial activity is dependent on the type of substituents and their position at the chloride moiety, as well as on the surface active properties of the compounds.
Chemo-immunotherapeutic antimalarials targeting isoprenoid biosynthesis
Zhang, Yonghui,Zhu, Wei,Liu, Yi-Liang,Wang, Hong,Wang, Ke,Li, Kai,No, Joo Hwan,Ayong, Lawrence,Gulati, Anmol,Pang, Ran,Freitas-Junior, Lucio,Morita, Craig T.,Oldfield, Eric
supporting information, p. 423 - 427 (2013/06/05)
We synthesized 30 lipophilic bisphosphonates and tested them in malaria parasite killing (targeting parasite geranylgeranyl diphosphate synthase, GGPPS) and human γδ T cell activation (targeting human farnesyl diphosphate synthase, FPPS). Similar patterns of activity were seen in inhibiting human FPPS and Plasmodium GGPPS, with short to medium chain-length species having most activity. In cells, shorter chain-length species had low activity, due to poor membrane permeability, and longer chain length species were poor enzyme inhibitors. Optimal activity was thus seen with ～C 10 side-chains, which have the best combination of enzyme inhibition and cell penetration. We also solved the crystal structure of one potent inhibitor, bound to FPPS. The results are of interest since they suggest the possibility of a combined chemo/immuno-therapeutic approach to antimalarial development in which both direct parasite killing and γδ T cell activation can be achieved with a single compound.
Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(-)-menthoxymethyl substituent
Pernak, Juliusz,Feder-Kubis, Joanna,Cieniecka-Ros?onkiewicz, Anna,Fischmeister, Cedric,Griffin, Scott T.,Rogers, Robin D.
, p. 879 - 892 (2008/02/12)
A series of 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-alkylimidazolium salts have been synthesized, producing both hydrophilic and hydrophobic chiral imidazolium ionic liquids. Their physicochemical properties, single-crystal X-ray structures, antimicrobial activities, and antielectrostatic effects were determined and these compounds have proven to represent not only potential new solvents in asymmetric synthesis, but also effective, disinfectants with antielectrostatic activity. Given the number and diversities of the possible conformations and interionic interactions, coupled with the chiral nature of the cations, it should come as no surprise that these salts exhibit ionic liquid behavior and are so difficult to crystallize. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Self-assembled N-alkylimidazolium perfluorooctanesulfonates
Mukai, Tomohiro,Yoshio, Masafumi,Kato, Takashi,Ohno, Hiroyuki
, p. 442 - 443 (2007/10/03)
Thermostability of a smectic A phase composed of N-alkyl-imidazolium heptadecafluorooctanesulfonate was improved by the formation of nonpolar layer composed of mixed perfluoroalkyl and aliphatic chains. Copyright
Synthesis of N-alkylated derivatives of imidazole as antibacterial agents
Khabnadideh,Rezaei,Khalafi-Nezhad,Bahrinajafi,Mohamadi,Farrokhroz
, p. 2863 - 2865 (2007/10/03)
N-Alkylation of imidazole, 2-methylimidazole and 2-methyl-4-nitroimidazole have been carried out to achieve effective antibacterial agents. The products were then investigated for antibacterial activity against Escherichia coil, Staphylococcus aureus and Pseudomonas aeruginosa. Antibacterial effects of 1-alkylimidazole derivatives increase as the number of carbons in alkyl chain increases up to nine carbons. Also substitution of 2-methyl and 2-methyl-4-nitro groups on imidazole ring increases the antibacterial activity.
Synthesis and surface activity of some imidazole, 1,2,4-triazole, and tetrazole derivatives
Abramzon,Pevzner,Kofman,Alam
, p. 1841 - 1848 (2007/10/03)
Imidazole, 1,2,4-triazole, and tetrazole derivatives containing large alkyl substituents are prepared, and their surface activity is studied.
Synthese et proprietes antibacteriennes et antifongiques d'une serie de 1-alkylimidazoles
Savignac, A. de,Roques, C.,Hinedi, M.,Michel, G.,Lattes, A.
, p. 449 - 454 (2007/10/02)
A homologous series of 1-alkylimidazoles (pentyl to octadecyl) has been obtained with a good yield (75-95percent) by the phase transfer catalyzed reaction of imidazole with the appropriate alkyl halides.The antifungal and antibacterial activities of these compounds were tested.A poor activity was observed towards the Gram-negative (Gram-) microorganisms, whereas the aerobic and anaerobic Gram-positive (Gram+) microorganisms and some yeasts (Pityrosporum ovale) were inhibited.We found that the inhibitory potency of such compounds increased with increasing chain length,passing through a maximum with chain length C10-C13 and decreased for the higher homologs.An explanation is suggested in relation to the ability of these compounds to bind with the active sites of the microorganisms and to adopt a conformation able to promote the migration through the biological membranes.
