Collect. Czech. Chem. Commun.
2011, 76, 1299-1305
https://doi.org/10.1135/cccc2011083
Published online 2011-10-30 22:38:34
Synthesis and antibacterial activity of unsaturated pyrimidine carboacyclonucleoside analogues
Jamal Krima,b, Bouchra Sillahib, Moha Taourirteb, Said Eddarirb and Joachim W. Engelsa,*
a Institut für Organische Chemie und Chemische Biologie, J. W. Goethe Universität, Max-von-Laue Str. 7, 60438 Frankfurt am Main, Germany
b Laboratoire de Chimie Bioorganique et Macromoléculaire, Faculté des Sciences et Techniques, Guéliz 40 000, Marrakech, Maroc
Abstract
The novel pyrimidine carboacyclonucleoside analogues containing propargylated aryl side chains were synthesized via palladium-catalyzed cross-coupling reactions as a key step. The synthesized compounds were screened for their antibacterial activity against four microorganisms: Staphylococcus aureus (CIP 53.154; Gram positive), Enterococcus hirae (CIP 58.55; Gram positive), Pseudomonas aeruginosa (CIP A22; Gram negative), Escherichia coli (CIP 54.8; Gram negative). Some of the prepared products showed promising antibacterial activity against the nosocomial E. hirae.
Keywords: N-Alkylation; Sonogashira cross-coupling; Thymine; Antibacterial activity; Alkynes; Alkylation; Antibiotics; Nucleobases; Palladium.
References: 30 live references.
