Synthesis and Antimicrobial Activity of Imidazolium and Triazolium Chiral Ionic Liquids

Paweł Borowiecki , Małgorzata Milner-Krawczyk , Dominika Brzezińska , Monika Wielechowska , Jan Plenkiewicz

Abstract

A simple and efficient procedure for the synthesis of new optically active imidazolium and triazolium ionic liquids in a three step reaction sequence is described. In the first step, the ring opening of 1,2-butylene oxide by imidazole or 1,2,4-triazole resulted in the formation of N-2-hydroxybutylimidazole and N-2-hydroxybutyl-1,2,4-triazole, respectively. In the second step, racemic mixtures of the secondary alcohols were resolved with good enantioselectivity by a lipase-catalyzed transesterification with enol esters (vinyl acetate and 1-acetoxy-2-methylcyclohexene). In the final step, the optically active intermediates were alkylated with several haloalkanes to yield optically active ionic liquids. The inhibitory activity of the synthesized ionic liquids was tested towards gram-negative and gram-positive bacteria and fungi.
Author Paweł Borowiecki (FC / IBC / DDTB)
Paweł Borowiecki,,
- Department Of Drug Technology And Biotechnology
, Małgorzata Milner-Krawczyk (FC / IBC / DDTB)
Małgorzata Milner-Krawczyk,,
- Department Of Drug Technology And Biotechnology
, Dominika Brzezińska (FC / IBC / DDTB)
Dominika Brzezińska,,
- Department Of Drug Technology And Biotechnology
, Monika Wielechowska (FC / IBC / DDTB)
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Jan Plenkiewicz (FC)
Jan Plenkiewicz,,
- Faculty of Chemistry
Journal seriesEuropean Journal of Organic Chemistry, ISSN 1434-193X, [1099-0690]
Issue year2013
Vol2013
No4
Pages712-720
Publication size in sheets0.5
Keywords in EnglishIonic liquids, Chirality, Enzyme catalysis, Kinetic resolution, Antibiotics, Antifungal agents
ASJC Classification1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry
DOIDOI:10.1002/ejoc.201201245
URL http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201245/abstract;jsessionid=96446A1CD0EFDE75646EBC2124DD7579.f01t02
Languageen angielski
File
Borowiecki_et_al-2013-European_Journal_of_Organic_Chemistry.pdf 589.59 KB
Score (nominal)35
Score sourcejournalList
ScoreMinisterial score = 35.0, 17-08-2020, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 17-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 29; WoS Citations = 29; GS Citations = 5.0; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.834; WoS Impact Factor: 2013 = 3.154 (2) - 2013=3.001 (5)
Citation count*5 (2015-10-29)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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