Journal
CHEMISTRY CENTRAL JOURNAL
Volume 11, Issue -, Pages -Publisher
SPRINGEROPEN
DOI: 10.1186/s13065-017-0294-0
Keywords
5,6-diaminouracil; Pyrimidodiazepine; Lumazine; Xanthine; Triazolouracil; Antimicrobial and antioxidant activities
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Background: Uracil derivatives have a great attraction because they play an important role in pharmacological activities. Pyrimidodiazepines, lumazines, triazolopyrimidines and xanthines have significant wide spectrum activities including anticancer, antiviral as well as antimicrobial activities. Results: A newly synthesized compounds pyrimido[4,5-b][1, 4] diazepines 5a-e, 6a-d, lumazines 7a-d, triazolo[4,5-d] pyrimidine 8 and xanthines 9, 10 was prepared in a good yields. The antimicrobial and antioxidant activities of compounds 5a, 5b, 6a, 6d and 8 exhibited a wide range activity against the pathogenic tested microbes (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, Candida albicans, and Saccharomyces cerevisiae). Compound 8 showed activity against the fungus Aspergillus niger. The highest antioxidant activity was noticed for compound 5a. Conclusions: A series of novel pyrimido[4,5-b][1, 4] diazepines 5a-e, 6a-d, lumazines 7a-d, triazolo[4,5-d] pyrimidine 8 and xanthines 9, 10 was prepared from 5,6-diamino-1-(2-chlorobenzyl) uracil 3 in good yields. Compounds 5a-e, 6a-d were prepared by sequential manipulation of 3 with alpha,beta-unsaturated ketones. Lumazines 7a-d were obtained from 3 by treatment with phenacyl bromides in the presence of TEA. Compound 8 was prepared by treatment of 3 with -HNO2, while xanthines 9, 10 were obtained from 3 by consecutive acetylation then intramolecular cyclodehydration or heating with malononitrile under solvent-free condition. The antimicrobial and antioxidant activity of this series was evaluated in vitro and they showed either weak or moderate activities.
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