Author(s)

Sarkar M. A. Kawsar^1*, Hamida A. Ara¹, Sheikh Aftab Uddin², Mohammed K. Hossain³, Shagir A. Chowdhury¹, Abul F. M. Sanaullah¹, Mohammad A. Manchur⁴, Imtiaj Hasan⁵, Yukiko Ogawa⁶, Yuki Fujii⁶, Yasuhiro Koide⁵, Yasuhiro Ozeki⁵

¹Laboratory of Carbohydrate and Protein Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, Bangladesh.
²The Institute of Marine Science, Faculty of Science, University of Chittagong, Chittagong, Bangladesh.
³Department of Pharmacy, Faculty of Biological Science, University of Chittagong, Chittagong, Bangladesh.
⁴Department of Microbiology, Faculty of Biological Science, University of Chittagong, Chittagong, Bangladesh.
⁵Laboratory of Glycobiology and Marine Biochemistry, Department of Life and Environmental System Science, Graduate School of NanoBio Sciences, Yokohama City University, Yokohama, Japan.
⁶Divisions of Microbiology, Graduate School of Pharmaceutical Science, Nagasaki International University, Nagasaki, Japan.

A new N-acetylsulfanilylation series of uridine have been synthesized in good yield using direct acylation method and afforded the 5’-O-N-acetylsulfanilyluridine. In order to obtain newer products, the 5’-O-N-acetylsulfanilyluridine derivative was further transformed to a series of 2’,3’-di-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were confirmed on the basis of their FTIR, ¹H-NMR spectroscopy, physicochemical properties and elemental analysis. All the synthesized uridine derivatives were tested for their in vitro antibacterial activity against six human pathogenic bacterial strains and for comparison standard antibiotic Ampicillin was also determined. The study revealed that the selectively acylated deriva-tives 5’-O-N-acetylsulfanilyl-2’,3’-di-O-lauroyluridine and 5’-O-N-acetylsulfanilyl-2’,3’-di-O-pivaloyluridine showed highest inhibition against Staphylococcus aureus and Bacillus cereus, respectively. We also observed that the introduction of hexanoyl, decanoyl, lauroyl, myristoyl and pivaloyl groups, the antibacterial functionality of the compound uridine increases. Another noteworthy observation was that the uridine derivatives were found comparatively more effective against Gram-positive microorganisms than those of Gram-negative microorganisms. In addition, the test chemicals were also tested for cyto-toxicity by brine shrimp lethality bioassay and compounds showed different rate mortality with different concentrations.

Uridine, Synthesis, Structure, Spectroscopy, Antibacterial, Cytotoxicity

Kawsar, S. , Ara, H. , Uddin, S. , Hossain, M. , Chowdhury, S. , Sanaullah, A. , Manchur, M. , Hasan, I. , Ogawa, Y. , Fujii, Y. , Koide, Y. and Ozeki, Y. (2015) Chemically Modified Uridine Molecules Incorporating Acyl Residues to Enhance Antibacterial and Cytotoxic Activities. International Journal of Organic Chemistry, 5, 232-245. doi: 10.4236/ijoc.2015.54023.