title: Synthesis and antibacterial evaluation of new N- and S-glycosides analogues with dinitrophenyl-substituted heterocyclic bases.
abstract: Four N- and S-glycosides 13-16 having nucleobases 7-12 binding to sugar molecules from one side and to 3,5-dinitrophenyl moieties from another side were synthesized from 3,5-dinitrobenzoic acid 2. The synthetic intermediates, hydrazide 5 and thiosemicarbazide 6 regarded as important key compounds for the synthesis of nucleobases 7-12, each was obtained by two approaches. Structures of synthesized compounds were determined spectroscopically. Antibacterial activities for synthetic intermediates and glycosides were assessed using the paper disk diffusion method against Gram-negative bacteria: Pseudomonas aeruginosa, Pseudomonas fluorescens, and Escherichia coli and Gram-positive bacteria: Bacillus cereus and Staphylococcus aureus. Some of the synthetic compounds showed variant activity against some of the microorganisms tested. Nucleobases 8-10 and 12 showed moderate to slight activity against microorganisms under test at relatively high concentration, while the N-glycosides 14 and 15 exhibited persistent effect even at lower concentrations. Commercially available antibiotics polymyxine and oxytetracycline were used as positive controls.
authors.affiliation: Laboratoire de Synthèse Organique Bioactive, Département de Chimie Organique Industrielle, Faculté de Chimie, Université des Sciences et de la Technologie d'Oran Mohamed Boudiaf-USTO-MB, BP. 1505, El-M'naouer, 31003, Oran, Algeria.
authors.forename: Fatima
authors.initials: F
authors.lastname: Belkhadem
authors.affiliation: Laboratoire de Synthèse Organique Bioactive, Département de Chimie Organique Industrielle, Faculté de Chimie, Université des Sciences et de la Technologie d'Oran Mohamed Boudiaf-USTO-MB, BP. 1505, El-M'naouer, 31003, Oran, Algeria. adelaliothman@gmail.com.
authors.forename: Adil A
authors.initials: AA
authors.lastname: Othman
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008826:Microbial Sensitivity Tests
chemical_list: D000900:Anti-Bacterial Agents; D006027:Glycosides; D006571:Heterocyclic Compounds
keywords: Antibacterial activity; Glycosides; Heterocycles; Nitrobenzoic acids; Nucleosides; Synthesis