Lipase-catalyzed kinetic resolution of novel antifungal N-substituted benzimidazole derivatives

Edyta Łukowska-Chojnacka , Monika Staniszewska , Małgorzata Bondaryk , Jan Maurin , Maria Bretner

Abstract

A series of new N-substituted benzimidazole derivatives was synthesized and their antifungal activity against Candida albicans was evaluated. The chemical step included synthesis of appropriate ketones containing benzimidazole ring, reduction of ketones to the racemic alcohols, and acetylation of alcohols to the esters. All benzimidazole derivatives were obtained with satisfactory yields and in relatively short times. All synthesized compounds exhibit significant antifungal activity against Candida albicans 900028 ATCC (% cell inhibition at 0.25 μg concentration > 98%). Additionally, racemic mixtures of alcohols were separated by lipase-catalyzed kinetic resolution. In the enzymatic step a transesterification reaction was applied and the influence of a lipase type and solvent on the enantioselectivity of the reaction was studied. The most selective enzymes were Novozyme SP 435 and lipase Amano AK from Pseudomonas fluorescens (E > 100).
Author Edyta Łukowska-Chojnacka ZTiBSL
Edyta Łukowska-Chojnacka,,
- Department Of Drug Technology And Biotechnology
, Monika Staniszewska
Monika Staniszewska,,
-
, Małgorzata Bondaryk
Małgorzata Bondaryk,,
-
, Jan Maurin
Jan Maurin,,
-
, Maria Bretner ZTiBSL
Maria Bretner,,
- Department Of Drug Technology And Biotechnology
Journal seriesChirality, ISSN 0899-0042
Issue year2016
Vol28
Pages347-354
Publication size in sheets0.5
Keywords in Englishazole; benzimidazole; enzyme; lipase; enzymatic transesterification; kinetic resolution; antifungal activity
DOIDOI:10.1002/chir.22591
URL http://onlinelibrary.wiley.com/doi/10.1002/chir.22591/full
Languageen angielski
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wdpb_publikacje_pliki_plik_publikacja_2823_org.pdf 258.78 KB
Score (nominal)25
ScoreMinisterial score [Punktacja MNiSW] = 20.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) [Punktacja MNiSW (2013-2016)] = 25.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor [Impact Factor WoS]: 2016 = 1.956 (2) - 2016=1.829 (5)
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