Year : 2014 | Volume
: 13 | Issue : 2 | Page : 130--136
Synthesis and antimicrobial evaluation of some novel benzoimidazole Schiff俟Q製 bases and their C-nucleoside derivatives
Eman A Abd El-Meguid, Nayera AM Abdelwahed
Department of Chemistry of Natural Products and Microbial Products, National Research Centre, Dokki, Egypt
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俟Q製 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俟Q製 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) .
Eman A Abd El-Meguid
Faculty of Pharmacy, Cairo University, Cairo
|How to cite this article:|
Abd El-Meguid EA, Abdelwahed NA. Synthesis and antimicrobial evaluation of some novel benzoimidazole Schiff's bases and their C-nucleoside derivatives.Egypt Pharmaceut J 2014;13:130-136
|How to cite this URL:|
Abd El-Meguid EA, Abdelwahed NA. Synthesis and antimicrobial evaluation of some novel benzoimidazole Schiff's bases and their C-nucleoside derivatives. Egypt Pharmaceut J [serial online] 2014 [cited 2021 Aug 2 ];13:130-136
Available from: http://www.epj.eg.net/article.asp?issn=1687-4315;year=2014;volume=13;issue=2;spage=130;epage=136;aulast=Abd;type=0