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Molecules 2015, 20(8), 14761-14776; doi:10.3390/molecules200814761

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

1
Department of Synthesis and Chemical Technology of Pharmaceutical Substances, Medical University of Lublin, Chodzki 4a, 20-093 Lublin, Poland
2
Department of Pharmaceutical Microbiology, Medical University of Lublin, Chodzki 1, 20-093 Lublin, Poland
3
School of Pharmacy, University of Eastern Finland, Yliopistonranta 1, P.O. Box 1627, FI-70211 Kuopio, Finland
4
Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3 Maja 54, 08-110 Siedlce, Poland
5
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 14 July 2015 / Revised: 14 July 2015 / Accepted: 10 August 2015 / Published: 13 August 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1304 KB, uploaded 13 August 2015]   |  

Abstract

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. View Full-Text
Keywords: antifungal; Candida albicans; X-ray analysis; 14-α-sterol demethylase; molecular modelling; synthesis antifungal; Candida albicans; X-ray analysis; 14-α-sterol demethylase; molecular modelling; synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Wróbel, T.M.; Kosikowska, U.; Kaczor, A.A.; Andrzejczuk, S.; Karczmarzyk, Z.; Wysocki, W.; Urbańczyk-Lipkowska, Z.; Morawiak, M.; Matosiuk, D. Synthesis, Structural Studies and Molecular Modelling of a Novel Imidazoline Derivative with Antifungal Activity. Molecules 2015, 20, 14761-14776.

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