Novel Nonsymmetrically p-Benzyl-Substituted (Benz)imidazole N-Heterocyclic Carbene-Silver(I) Acetate Complexes : Synthesis and Biological Evaluation
Joint Authors
Malenke, Sina
Tacke, Matthias
Paradisi, Francesca
Patil, Siddappa
Lally, Grainne
Quaglia, Daniela
Müller-Bunz, Helge
Hackenberg, Frauke
Deally, Anthony
Source
International Journal of Inorganic Chemistry
Issue
Vol. 2012, Issue 2012 (31 Dec. 2012), pp.1-13, 13 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2012-03-01
Country of Publication
Egypt
No. of Pages
13
Main Subjects
Abstract EN
Nonsymmetrically substituted N-heterocyclic carbene (NHC) precursors 1a–d and 3a–d were synthesised by first reacting 1H-(benz)imidazole with p-cyanobenzyl bromide to give 4-(1H-imidazole-1-ylmethyl)benzonitrile (1) and 4-(1H-benzimidazole-1-ylmethyl)benzonitrile (3) and afterwards introducing benzyl bromide, 1-(bromomethyl)-4-methylbenzene, 1-(bromomethyl)-4-methoxybenzene, and methyl 4-(bromomethyl)benzoate.
The NHC-silver(I) acetate complexes (1-benzyl-3-(4-cyanobenzyl)-2,3-dihydro-1H-imidazole-2-ylidene) silver(I) acetate (2a), (1-(4-cyanobenzyl)-3-(4-methylbenzyl)-2,3-dihydro-1H-imidazole-2-ylidene) silver(I) acetate (2b), (1-(4-cyanobenzyl)-3-[4-(methoxycarbonyl)benzyl]-2,3-dihydro-1H-imidazole-2-ylidene) silver(I) acetate (2c), (1-benzyl-3-(4-cyanobenzyl)-2,3-dihydro-1H-benzimidazole-2-ylidene) silver(I) acetate (4a), (1-(4-cyanobenzyl)-3-(4-methylbenzyl)-2,3-dihydro-1H-benzimidazole-2-ylidene) silver(I) acetate (4b), (1-(4-cyanobenzyl)-3-(4-methoxybenzyl)-2,3-dihydro-1H-benzimidazole-2-ylidene) silver(I) acetate (4c), and (1-(4-cyanobenzyl)-3-[4-(methoxycarbonyl)benzyl]-2,3-dihydro-1H-benzimidazole-2-ylidene) silver(I) acetate (4d) were yielded by reacting these NHC precursors with silver(I) acetate.
The silver(I) acetate complex 4b was characterised by single crystal X-ray diffraction.
Preliminary in vitro antibacterial studies against the Gram-positive bacteria Staphylococcus aureus and the Gram-negative bacteria Escherichia coli, using the Kirby-Bauer disc diffusion method, were carried out on the seven NHC-silver(I) acetate complexes 2a–c and 4a–d.
Also the IC50 values of these seven complexes were determined by an MTT-based assay against the human renal cancer cell line Caki-1.
The complexes 2a–c and 4a–c revealed the following IC50 values, respectively, 25 (±1), 15 (±2), 5.4 (±0.8), 16 (±2), 7.1 (±1), 20 (±4), and 14 (±1) μM.
American Psychological Association (APA)
Hackenberg, Frauke& Deally, Anthony& Lally, Grainne& Malenke, Sina& Müller-Bunz, Helge& Paradisi, Francesca…[et al.]. 2012. Novel Nonsymmetrically p-Benzyl-Substituted (Benz)imidazole N-Heterocyclic Carbene-Silver(I) Acetate Complexes : Synthesis and Biological Evaluation. International Journal of Inorganic Chemistry،Vol. 2012, no. 2012, pp.1-13.
https://search.emarefa.net/detail/BIM-447333
Modern Language Association (MLA)
Hackenberg, Frauke…[et al.]. Novel Nonsymmetrically p-Benzyl-Substituted (Benz)imidazole N-Heterocyclic Carbene-Silver(I) Acetate Complexes : Synthesis and Biological Evaluation. International Journal of Inorganic Chemistry No. 2012 (2012), pp.1-13.
https://search.emarefa.net/detail/BIM-447333
American Medical Association (AMA)
Hackenberg, Frauke& Deally, Anthony& Lally, Grainne& Malenke, Sina& Müller-Bunz, Helge& Paradisi, Francesca…[et al.]. Novel Nonsymmetrically p-Benzyl-Substituted (Benz)imidazole N-Heterocyclic Carbene-Silver(I) Acetate Complexes : Synthesis and Biological Evaluation. International Journal of Inorganic Chemistry. 2012. Vol. 2012, no. 2012, pp.1-13.
https://search.emarefa.net/detail/BIM-447333
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-447333