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. 1982 Sep 11;10(17):5285–5295. doi: 10.1093/nar/10.17.5285

Synthesis and biological properties of 2'-deoxy-5-vinyluridine and 2'deoxy-5-vinylcytidine.

S G Rahim, M J Duggan, R T Walker, A S Jones, R L Dyer, J Balzarini, E De Clercq
PMCID: PMC320871  PMID: 6292837

Abstract

Rapid and efficient syntheses for the preparation of 2'-deoxy-5-vinyluridine and 2'-deoxy-5-vinylcytidine are described starting from nucleoside precursors. Contrary to some previous reports, 2-deoxy-5-vinyluridine has be found to be quite stable under normal laboratory conditions but when tested in animals shows neither toxicity nor anti-leukemic (L1210 cells) or anti-parasitic (Plasmodium berghei) activity. 2'-Deoxy-5-vinylcytidine appears to polymerise readily. It is much less toxic to cell cultures than 2'-deoxy-5'vinyluridine but is almost as active against herpes virus replication (ID50:0.2 microgram/ml) for both type 1 and type 2 herpes virus (selectivity index:225).

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bergstrom D. E., Ruth J. L. Letter: Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates. J Am Chem Soc. 1976 Mar 17;98(6):1587–1589. doi: 10.1021/ja00422a056. [DOI] [PubMed] [Google Scholar]
  2. Chelton E. T., Duggan M., Hunston R. N., Jones A. S., O'Leary M. K., Overton D. J., Walker R. T. Incorporation of 5-substituted uracil derivatives into nucleic acids. The isolation and gamma-radiation-sensitivity of bacteriophage T3 containing the thymine analogue 5-vinyluracil. Biochem J. 1980 Apr 1;187(1):257–260. doi: 10.1042/bj1870257. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Chelton E. T., Evans C. H., Jones A. S., Walker R. T. Incorporation of 5-substituted uracil derivatives into nucleic acids. II. Incorporation of 5-vinyluracil into the DNA of Escherichia coli. Biochim Biophys Acta. 1973 Jun 8;312(1):38–44. doi: 10.1016/0005-2787(73)90050-6. [DOI] [PubMed] [Google Scholar]
  4. Chelton E. T., Jones A. S., Walker R. T. The sensitivity of Mycoplasma mycoides var. capri cells to gamma-radiation after growth in a medium containing the thymine analogue 5-vinyluracil. Biochem J. 1979 Sep 1;181(3):783–785. doi: 10.1042/bj1810783. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Cheng Y. C., Domin B. A., Sharma R. A., Bobek M. Antiviral action and cellular toxicity of four thymidine analogues: 5-ethyl-,5-vinyl-, 5-propyl-, and 5-allyl-2'- deoxyuridine. Antimicrob Agents Chemother. 1976 Jul;10(1):119–122. doi: 10.1128/aac.10.1.119. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. De Clercq E., Balzarini J., Descamps J., Huang G. F., Torrence P. F., Bergstrom D. E., Jones A. S., Serafinowski P., Verhelst G., Walker R. T. Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 2'-deoxycytidines. Mol Pharmacol. 1982 Jan;21(1):217–223. [PubMed] [Google Scholar]
  7. De Clercq E., Balzarini J., Torrence P. F., Mertes M. P., Schmidt C. L., Shugar D., Barr P. J., Jones A. S., Verhelst G., Walker R. T. Thymidylate synthetase as target enzyme for the inhibitory activity of 5-substituted 2'-deoxyuridines on mouse leukemia L1210 cell growth. Mol Pharmacol. 1981 Mar;19(2):321–330. [PubMed] [Google Scholar]
  8. De Clercq E., Descamps J., De Somer P., Barr P. J., Jones A. S., Walker R. T. (E)-5-(2-Bromovinyl)-2'-deoxyuridine: a potent and selective anti-herpes agent. Proc Natl Acad Sci U S A. 1979 Jun;76(6):2947–2951. doi: 10.1073/pnas.76.6.2947. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. De Clercq E., Descamps J., Verhelst G., Walker R. T., Jones A. S., Torrence P. F., Shugar D. Comparative efficacy of antiherpes drugs against different strains of herpes simplex virus. J Infect Dis. 1980 May;141(5):563–574. doi: 10.1093/infdis/141.5.563. [DOI] [PubMed] [Google Scholar]
  10. Fissekis J. D., Sweet F. The chemistry of some 5-(2-hydroxyalkyl)uracil derivatives and a synthesis of 5-vinyluracil. J Org Chem. 1973 Jan 26;38(2):264–269. doi: 10.1021/jo00942a015. [DOI] [PubMed] [Google Scholar]
  11. Schildkraut I., Cooper G. M., Greer S. Selective inhibition of the replication of herpes simplex virus by 5-halogenated analogues of deoxycytidine. Mol Pharmacol. 1975 Mar;11(2):153–158. [PubMed] [Google Scholar]
  12. Sharma R. A., Bobek M. Synthesis of 5-vinyluridine and 5-vinyl-2'-deoxyuridine as new pyrimidine nucleoside analogs. J Org Chem. 1975 Aug 8;40(16):2377–2379. doi: 10.1021/jo00904a025. [DOI] [PubMed] [Google Scholar]
  13. Walker R. T., Jones A. S., Rahim S. G., Serafinowski P., De Clercq E. The synthesis and properties of some 5-substituted uracil derivatives. Nucleic Acids Symp Ser. 1981;(9):21–24. [PubMed] [Google Scholar]

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