One pot synthesis, antimicrobial and antioxidant activities of fused uracils: pyrimidodiazepines, lumazines, triazolouracil and xanthines

Résumé

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. 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 . 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 α , β -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 HNO 2 , 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. Several pyrimido[4,5- b ][1,4]diazepines, lumazines, triazolo-, and imidazolopyrimidines were synthesized from the starting compound 4,5-diaminouracils. The newly synthesized compounds were screened for both antimicrobial and antioxidant activities.

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