Synthesis and antimicrobial evaluation of some novel benzoimidazole Schiff's bases and their C-nucleoside derivatives | ||||
| Egyptian Pharmaceutical Journal | ||||
| Volume 13, Issue 2, July 2014, Page 130-136 PDF (1.09 MB) | ||||
| DOI: 10.4103/1687-4315.147082 | ||||
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| Authors | ||||
| Eman A. Abd El-Meguid; Nayera A.M. Abdelwahed | ||||
| Abstract | ||||
| 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 () was prepared through the reaction of (3,4-diamino-phenyl)-phenyl-methanone () with 4-cyanobenzaldehyde in absolute ethanol. Stirring compound 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 (). A series of Schiff's bases derivatives and were prepared by condensation of hydrazide with different monosaccharides and/or with arenaldehydes. Treatment of with thioglycolic acid led to the formation of the C-nucleosides (), whereas treatment of with thioglycolic acid yielded the corresponding 2-arylthiazolidin-4-one (). Results and conclusion Compound showed the highest antimicrobial activity against , (gram-positive bacteria), , and (gramnegative bacteria), and and (fungi). | ||||
| Keywords | ||||
| antimicrobial activity; 2-aryl-thiazolidinone-4-one; 4-benzoimidazol-2-yl; C-nucleoside; sugar-Schiff's base | ||||
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