Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Partition Property of 5-Nitrothuopyrimidine Nucleoside

  • Published : 1997.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

5-Nitrouracil and 5-nitrouridine derivatives which C-2 and C-4 oxo-groups of the pyrimidine base were replaced by thio groups were synthesized. The lipophilicities of thiopyrimidine bases were enhanced significantly as indicated by P-values. Oxygen-sulfur exchange leading to 2-thiouracil (2) and 2,4-dithiouracil (3) were associated with 1.4- and 2.6-fold increase in P-value relative to that of uracil (1). The P-values of 5-nitro-2-thiouracil (5) and 5-nitro-2,4-dithiouracil (6) were increased 13.2- and 79.8-fold relative to that of 5-nitrouracil (4). Most of the 5-nitrothiopyrimidine bases and their nucleosides were found to be moderately active against Staphylococcus aureus and Escherichia coli except 5-nitrouracil (4).

Keywords

References

  1. J. Med. Chem. v.13 no.5 Coats, E.;Glave, W. R.;Hansch, C.
  2. J. Med. Chem. v.13 no.3 Baker, B. R.;James, L. K.
  3. J. Am. Chem. Soc. v.80 fox, J. J.;Wempen, I.;Hampton, A.;doerr, I. L.
  4. J. Med. Chem. v.33 Palomino, E.;Meltsner, B. R.;Kessel, D.;Morwitz, J. P.
  5. Antibiotics in Laboratory Medicine(3rd ed.) Lorian, V
  6. Microscale Organic Laboratory Mayo, D. W.;Pike, R. M.;Butcher, S. S.
  7. J. Biol. Chem. v.243 Kessel, D.
  8. Intrduction to Chromatography Robbit, J. M.;Schqarting, A. E.;Gritter, R. J.
  9. Chem. Pharm. Bull. v.16 no.9 Ueda, T.;Iida, Y.;Ikeda, K.;Mizuno, Y.
  10. J. Org. Chem. v.42 no.24 Huang, G. F.;Torrence, P. F.
  11. Nucleoside Analogues Chemistry, Biology, and Medical Applications Walker, R. T.;Clercq, E. D.;Eckstein, F.
  12. Synthetic Procedures in Nucleic Acid Chemistry v.1 Zorbach, W. W.;tipson, R. S.
  13. Biologically active material and microorganism Cheon, H. K.