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Molecules 2015, 20(6), 10360-10376; doi:10.3390/molecules200610360

Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes

1
Department of Chemistry and Biochemistry, Faculty of Agronomy, Mendel University in Brno, Zemedelska 1, Brno CZ-613 00, Czech Republic
2
Central European Institute of Technology, Brno University of Technology, Technicka 3058/10, Brno CZ-616 00, Czech Republic
3
Institute of Chemistry, Environmental Protection and Biotechnology, Jan Dlugosz University of Czestochowa, Armii Krajowej 13/15, Czestochowa PL-42-201, Poland
4
Environmental Inorganic Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, Göteborg SE-412 96, Sweden
5
Department of Traumatology at the Medical Faculty, Masaryk University and Trauma Hospital of Brno, Ponavka 6, Brno CZ-662 50, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 31 March 2015 / Revised: 22 May 2015 / Accepted: 29 May 2015 / Published: 4 June 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1287 KB, uploaded 5 June 2015]   |  

Abstract

1-(1H-Benzimidazol-2-yl)-N-(1H-benzimidazol-2-ylmethyl)methanamine (abb) and 2-(1H-benzimidazol-2-ylmethylsulfanylmethyl)-1H-benzimidazole (tbb) have been prepared and characterized by elemental analysis. These bis(benzimidazoles) have been further used in combination with trithiocyanuric acid for the preparation of complexes. The crystal and molecular structures of two of them have been solved. Each nickel atom in the structure of trinuclear complex [Ni3(abb)3(H2O)3(μ-ttc)](ClO4)3·3H2O·EtOH (1), where ttcH3 = trithiocyanuric acid, is coordinated with three N atoms of abb, the N,S donor set of ttc anion and an oxygen of a water molecule. The crystal of [(tbbH2)(ttcH2)2(ttcH3)(H2O)] (2) is composed of a protonated bis(benzimidazole), two ttcH2 anions, ttcH3 and water. The structure is stabilized by a network of hydrogen bonds. These compounds were primarily synthesized for their potential antimicrobial activity and hence their possible use in the treatment of infections caused by bacteria or yeasts (fungi). The antimicrobial and antifungal activity of the prepared compounds have been evaluated on a wide spectrum of bacterial and yeast strains and clinical specimens isolated from patients with infectious wounds and the best antimicrobial properties were observed in strains after the use of ligand abb and complex 1, when at least 80% growth inhibition was achieved. View Full-Text
Keywords: coordination compounds; biological activity; trithiocyanuric acid; trimercaptotriazine; single crystal X-ray diffraction; benzimidazole coordination compounds; biological activity; trithiocyanuric acid; trimercaptotriazine; single crystal X-ray diffraction; benzimidazole
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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

Kopel, P.; Wawrzak, D.; Langer, V.; Cihalova, K.; Chudobova, D.; Vesely, R.; Adam, V.; Kizek, R. Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes. Molecules 2015, 20, 10360-10376.

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