Synthesis of 1-(4-Thio-${\alpha},{\beta}$-D-ribofuranosyl)-5-halogenouracils (II). 5-Fluoro-4'-thiouridine and 5-Chloro-4'-thio-uridine

5-할로겐 치환된 Uracil의 4-Thiosugar Nucleosides의 합성에 관한 연구 (제2보). 5-Fluoro-4'-thiouridine과 5-Chloro-4'-thiouridine의 합성

  • Jack C Kim (Department of Chemistry, College of Liberal Arts Science Busan National University) ;
  • Won-Jei Cho (Department of Chemistry, College of Liberal Arts Science Busan National University) ;
  • Miroslay Bobek (Department of Experimental Therapeutics) ;
  • Roy L. Whistler (Department of Biochemistry)
  • Published : 1975.12.30

Abstract

The syntheses of anomeric mixtures of 1-(4-thio-${\alpha},{\beta}$-D-ribofuranosyl)-5-fluoro-and 5-chlorouracils from their corresponding bis(trimethylsilyl) derivatives of 5-halogenouracils and 2,3,5-tri-O-acetyl-4-thio-${\alpha},{\beta}$-D-ribofuranosyl chloride are described. Preliminary biochemical studies showed that in leukemia 1210 cells and Streptococcus faecium, the ${\beta}$-anomeric 5-chloro-4'-thionucleoside is not greatly different from the corresponding 4'-oxygen analog. However, the 5-fluoro-4'-thionucleoside showed a growth inhibitory effect more than that of the oxygen counterpart. The potential chemotherapeutic use of the analog is to warrant further study.

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References

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