Synthesis, Structural Studies and Molecular Modelling of a Novel Imidazoline Derivative with Antifungal Activity

Tomasz M. Wróbel; Urszula Kosikowska; Agnieszka A. Kaczor; Sylwia Andrzejczuk; Zbigniew Karczmarzyk; Waldemar Wysocki; Zofia Urbańczyk-Lipkowska; Maja Morawiak; Dariusz Matosiuk

doi:10.3390/molecules200814761

Molecules (Aug 2015)

Synthesis, Structural Studies and Molecular Modelling of a Novel Imidazoline Derivative with Antifungal Activity

Tomasz M. Wróbel,
Urszula Kosikowska,
Agnieszka A. Kaczor,
Sylwia Andrzejczuk,
Zbigniew Karczmarzyk,
Waldemar Wysocki,
Zofia Urbańczyk-Lipkowska,
Maja Morawiak,
Dariusz Matosiuk

Affiliations

Tomasz M. Wróbel: Department of Synthesis and Chemical Technology of Pharmaceutical Substances, Medical University of Lublin, Chodzki 4a, 20-093 Lublin, Poland
Urszula Kosikowska: Department of Pharmaceutical Microbiology, Medical University of Lublin, Chodzki 1, 20-093 Lublin, Poland
Agnieszka A. Kaczor: Department of Synthesis and Chemical Technology of Pharmaceutical Substances, Medical University of Lublin, Chodzki 4a, 20-093 Lublin, Poland
Sylwia Andrzejczuk: Department of Pharmaceutical Microbiology, Medical University of Lublin, Chodzki 1, 20-093 Lublin, Poland
Zbigniew Karczmarzyk: Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3 Maja 54, 08-110 Siedlce, Poland
Waldemar Wysocki: Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3 Maja 54, 08-110 Siedlce, Poland
Zofia Urbańczyk-Lipkowska: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland
Maja Morawiak: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland
Dariusz Matosiuk: Department of Synthesis and Chemical Technology of Pharmaceutical Substances, Medical University of Lublin, Chodzki 4a, 20-093 Lublin, Poland

DOI: https://doi.org/10.3390/molecules200814761
Journal volume & issue: Vol. 20, no. 8
pp. 14761 – 14776

Abstract

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Six novel imidazoline derivatives were synthesized and tested in antifungal assays. One of the compounds, N-cyclohexyl-2-imino-3-(4-nitrophenyl)imidazolidine-1-carboxamide showed moderate activity against several clinical strains of Candida albicans. Its structure was solved by X-ray crystallography and its mode of action was deduced using molecular modelling. It was found to be similar to that of fluconazole. The potential for further optimization including SAR of the compound is briefly discussed.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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