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

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 t...

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Autores principales: Kopel, Pavel, Wawrzak, Dorota, Langer, Vratislav, Cihalova, Kristyna, Chudobova, Dagmar, Vesely, Radek, Adam, Vojtech, Kizek, Rene
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272323/
https://www.ncbi.nlm.nih.gov/pubmed/26053490
http://dx.doi.org/10.3390/molecules200610360
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author Kopel, Pavel
Wawrzak, Dorota
Langer, Vratislav
Cihalova, Kristyna
Chudobova, Dagmar
Vesely, Radek
Adam, Vojtech
Kizek, Rene
author_facet Kopel, Pavel
Wawrzak, Dorota
Langer, Vratislav
Cihalova, Kristyna
Chudobova, Dagmar
Vesely, Radek
Adam, Vojtech
Kizek, Rene
author_sort Kopel, Pavel
collection PubMed
description 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 [Ni(3)(abb)(3)(H(2)O)(3)(μ-ttc)](ClO(4))(3)·3H(2)O·EtOH (1), where ttcH(3) = 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 [(tbbH(2))(ttcH(2))(2)(ttcH(3))(H(2)O)] (2) is composed of a protonated bis(benzimidazole), two ttcH(2) anions, ttcH(3) 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.
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spelling pubmed-62723232018-12-31 Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes Kopel, Pavel Wawrzak, Dorota Langer, Vratislav Cihalova, Kristyna Chudobova, Dagmar Vesely, Radek Adam, Vojtech Kizek, Rene Molecules Article 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 [Ni(3)(abb)(3)(H(2)O)(3)(μ-ttc)](ClO(4))(3)·3H(2)O·EtOH (1), where ttcH(3) = 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 [(tbbH(2))(ttcH(2))(2)(ttcH(3))(H(2)O)] (2) is composed of a protonated bis(benzimidazole), two ttcH(2) anions, ttcH(3) 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. MDPI 2015-06-04 /pmc/articles/PMC6272323/ /pubmed/26053490 http://dx.doi.org/10.3390/molecules200610360 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kopel, Pavel
Wawrzak, Dorota
Langer, Vratislav
Cihalova, Kristyna
Chudobova, Dagmar
Vesely, Radek
Adam, Vojtech
Kizek, Rene
Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes
title Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes
title_full Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes
title_fullStr Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes
title_full_unstemmed Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes
title_short Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes
title_sort biological activity and molecular structures of bis(benzimidazole) and trithiocyanurate complexes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272323/
https://www.ncbi.nlm.nih.gov/pubmed/26053490
http://dx.doi.org/10.3390/molecules200610360
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