Synthesis of 1-(4'-Thio-${\alpha},{\beta}$-D-ribofuransyl)-5-halogeno Uracils (I)

5-할로겐 치환 uracil 들의 4-Thiosugar Nucleosides의 합성 (제 1 보)

  • Kim Jack C. (Department of Chemistry, College of Liberal Arts and Sciences, Busan National University) ;
  • Lee Euk-suck (Department of Chemistry, College of Liberal Arts and Sciences, Busan National University) ;
  • Kim Chang-bae (Department of Chemistry, Dan-kook University) ;
  • Bobek Miroslav (Department of Experimental Therapeutics, Roswell Park Memorial Institute) ;
  • Whistlee Roy L. (Department of Biochemistry, Purdue University)
  • Published : 1975.04.30

Abstract

The 4'-thio analogs of the 5-bromo-and 5-iodo-pyrimidine nucleosides were prepared by condensation of 2,3,5-tri-O-acetyl-4-thio-${\alpha},{\beta}$-D-ribofuranosyl chloride with the chloromercury derivatives of 5-halogeno-2,4-bis(trimethylsiloxy)pyrimidine, followed by the removal of the protecting groups. Although the biological activities of the 4'-thio derivatives are not greatly different from the corresponding 4'-oxygen analogs in this preliminary test, the fact that the 4'-thio analogs have comparableihigh activities, is of interest, and indicates the value of further biochemical examinations.

Keywords

References

  1. Progress in Chemistry and Chemical Industry v.14 J. C. Kim
  2. Carbohydrate Res. v.31 J. C. Kim;R. L. Whistler
  3. J. Med. Chem. v.13 M. Bobek;R. L. Whistler
  4. J. Org. Chem. v.33 H. Iwamma;T. Flashisume
  5. J. Org. Chem. v.29 R. L. Whistler;W. E. Dick;T. R. Ingle;R. M. Rowell;B. Urbas
  6. J. Org. Chem. v.31 B. Urbas;R. L. Whistler
  7. J. Org. Chem. v.34 M. P. Kotick;C. Szantay;T. J. Bardos
  8. Personal Communication A. Bloch;M. Bobek
  9. Chem. Pharm. Bull. v.12 T. Nishimura;B. Shimuzu;I. Iwai
  10. J. Med. Chem. v.13 G. L. Szekeres;T. J. Bardos
  11. J. Org. Chem. v.27 E. J. Reist;A. Benitz;L. Goodman;B. R. Baker;W. W. Lee