Year : 2014  |  Volume : 13  |  Issue : 2  |  Page : 130-136

Synthesis and antimicrobial evaluation of some novel benzoimidazole Schiff's bases and their C-nucleoside derivatives

Department of Chemistry of Natural Products and Microbial Products, National Research Centre, Dokki, Egypt

Correspondence Address:
Eman A Abd El-Meguid
Faculty of Pharmacy, Cairo University, Cairo
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Source of Support: None, Conflict of Interest: None

DOI: 10.4103/1687-4315.147082

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Background and objectives The discovery of C-nucleosides and continuous study of their biological activities led us to construct new compounds containing 4-(5-benzoyl-benzoimidazol-2)-benzoic acid hydrazide Schiff's bases incorporated into different aldoses, thiazolidinones, and/or their C-nucleoside analogues. The aim of this study is to describe the synthesis of some new heterocycles derived from 4-(5-benzoyl-benzoimidazol-2)-benzoic acid hydrazide and to evaluate their antimicrobial activities. Materials and methods The starting material 4-(5-benzoyl-1H-benzoimidazol-2-yl)-benzonitrile ( 2 ) was prepared through the reaction of (3,4-diamino-phenyl)-phenyl-methanone ( 1 ) with 4-cyanobenzaldehyde in absolute ethanol. Stirring compound 2 with 70% sulfuric acid yielded benzoic acid derivative 3 , followed by esterification and refluxing with hydrazine hydrate to yield the corresponding 4-(5-benzoyl-1H-benzoimidazol-2-yl)-benzoic acid hydrazide ( 5 ). A series of Schiff's bases derivatives 6a-c and 8a-e were prepared by condensation of hydrazide 5 with different monosaccharides and/or with arenaldehydes. Treatment of 6a-c with thioglycolic acid led to the formation of the C-nucleosides ( 7a-c ), whereas treatment of 8a-e with thioglycolic acid yielded the corresponding 2-arylthiazolidin-4-one ( 9a-e ). Results and conclusion Compound 6b showed the highest antimicrobial activity against Bacillus subtilis, Staphylococcus aureus (gram-positive bacteria), Escherichia coli, and Pseudomonas aeuroginosa (gram-negative bacteria), and Candida albicans and Aspergillus niger (fungi) .

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