Synthesis of new uracil derivatives and their sugar hydrazones with potent antimicrobial, antioxidant and anticancer activities

Abstract

6-(4-Chloro-3-nitrophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4) was prepared and was reacted with ethyl chloroacetate, hydrazine hydrate, 4-chloroaniline, formaldehyde, acetic anhydride, formic acid, carbon disulfide, 4-cyanobenzaldehyde, triethyl orthoformate, D-sugars, 4-aminoacetophenone, benzoyl choride and cyclohexanone to afford a series of new uracil derivatives (5–18). Examination of some of the prepared compounds for their antimicrobial, antioxidant and anticancer activities was conducted. Among the tested samples, compound 17 was the most active substance against the gram-positive bacteria and was more potent than the reference drug Cefoperazone. Moreover, the antibacterial activity of 17 was higher against gram-negative bacteria. Compounds 6 and 13 reached a higher scavenging ability toward DPPH radicals and are better candidates for antioxidant activity. Also, compounds 6 and 13 had no significant anticancer activity toward liver cancer (Hep G2) and breast cancer (MCF-7) cell lines.

Graphical Abstract

Keywords:

• Uracil
• derivatives
• antimicrobial
• antioxidant
• anticancer
• activity

Acknowledgments

A. F. El Farargy thanks Prof. Dr. N. Krausa, Lehrstuhl für Organische Chemie, TU Dortmund, Germany, for his continuous help and repeated invitation. We thank the Alexander von Humboldt-Foundation (Germany) for the continuous help and support to F. M. Abdelrazek through granting short research fellowships, help and repeated invitation. Thanks are also due to Professor Peter Metz, Fakultät Chemie und Lebensmittelchemie, TU Dresden for his repeated invitations and generous hospitality.