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Original Articles

A CONVENIENT METHOD FOR THE SYNTHESIS AND RANEY NICKEL DESULFURIZATION OF 5′-DEOXY-5′ -M ETHYLTHIOADENOSINE

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Pages 149-152 | Received 08 Apr 1993, Accepted 18 Oct 1993, Published online: 23 Sep 2006

References

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  • Lewis , A. F. and Townsend , L. B. 1982 . J. Amer. Chem. Soc. , 104 : 1073 – 1077 . The biological activity (i.e., cytotoxicity) of nucleosides is commonly thought to result from their conversion to the corresponding 5′-phosphates, cf. Blocking this conversion might be accomplished by conversion of the 5′-hydroxy group to a halo group or a hydrogen atom. Thus, we observed that the nucleoside antibiotic tubercidin, had an IC50 of 50 ng/mL against EL4 mouse leukemia cells in culture, while 5′-chloro-5′-deoxytubercidin lacked toxicity at 10. μg/mL. A similar effect was observed for formycin-A, which also had an IC50, of 50 ng/mL, while the 5′-chloro-5′-deoxy derivative was non-toxic at 100 μg/mL.
  • Kissman , H. M. and Baker , B. R. 1957 . J. Amer. Chem. Soc. , 79 : 5534 – 55440 .
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  • Robbins , M. J. , Hansske , F. , Wnuk , S. F. and Kanai , T. 1991 . Can. J. Chem. , 69 : 1468 – 1474 .

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