Skip to main content
SpringerLink
Log in

The oxidative iodination of pyrimidine bases and their nucleosides using iodine/dimethylformamide/ m-chloroperbenzoic acid

  • Original Articles
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Pyrimidine bases and their nucleosides were oxidatively iodinated at C-5 position by the reaction of iodine in DMF (dimethylformamide) with MCPBA (m-chloroperbenzoic acid) under mild conditions. For uracil derivatives such as uracil1a, 1,3-dimethyluracil1b, uridine1c, and 2′-deoxyuridine1d, the corresponding 5-iodo derivatives were obtained in high yields (71–95%). The iodination of cytidine3a and 2′-deoxycytidine3b was achieved in moderate yields (41–56%).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  1. (a) Roy-Burman, P.Analogues of Nucleic Acid Components. Springer-Verlag New York. 1970. (b) Uesugi, S. Ikehara, M.: Studies on nucleosides and nucleotides. LXXXI Carbon-13 magnetic resonance spectra of 8-substituted purine nucleotides. Effects of various phosphate groups on the chemical shifts and conformation of nucleotides.Chem. Pharm. Bull. 26, 3040 (1978). (c) Lin, T-S. Chen, M. S. McLaren, C. Gao, Y-S. Ghazzouli, I. and Prusoff, W. H.: Synthesis and antiviral activity of various 3′-azido, 3′-amino, 2′,3′-unsaturated, and 2′,3′-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.J. Med. Chem. 30, 440 (1987).

    Google Scholar 

  2. (a) Bradshaw, T. K. and Hutchinson, D. W.: 5-Substituted pyrimidine nucleosides and nucleotides.Chem. Soc. Rev. 6, 43 (1977). (b) Long, R. A. Robins, R. K. and Townsend, L. B.: Purine nucleosides. XV. The synthesis of 8-amino-and 8-substituted aminopurine nucleosides.J. Org. Chem.,32, 2751 (1967). (c) Robins, M. J. and Barr, P. J.: Nucleic acid related compounds. 39. Efficient conversion of 5-iodo to 5-alkynyl and derived 5-substituted uracil based and nucleosides.J. Org. Chem.,48, 1854 (1983). (d) De Clercq, E. Descamps, J. Balzarini, J. Giziewicz, J. Barr, P. J. and Robins, M. J.: Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.J. Med. Chem.,26, 661 (1983).

    Article  CAS  Google Scholar 

  3. (a) Prusoff, W. H. Holmes, W. L. and Welch, A. D.: Nonutilization of radioactive iodinated uracil, uridine, and orotic acid by animal tissuein vivo.Cancer Res. 13, 221 (1953). (b) Prusoff, W.H.: Synthesis and biological activities of iododeoxyuridine, an analog of thymidine.Biochim. Biophys. Acta.,32, 295 (1959).

    PubMed  CAS  Google Scholar 

  4. (a) Lipkin, D. Howard, F. B. Nowotny, D. and Sano, M.: The iodination of nucleosides and nucleotides.J. Biol Chem. 238, 2249 (1963). (b) Das, B. and Kundu, N. G.: An efficient method for the iodination of C-5 position of dialkoxypyrimidines and uracil bases.Synthetic Commun.,18, 855 (1988).

    Google Scholar 

  5. Robins, M. J. Barr, P. J. Giziewicz, J.: Nucleic acids related compounds. 38. Smooth and highyield iodination and chlorination at C-5 of uracil bases andp-toluyl-protected nucleosides.Can. J. Chem. 60, 554 (1982).

    Article  CAS  Google Scholar 

  6. Asakura, J. I. and Robins, M. J.: Cerium (IV)-mediated halogenation at C-5 of uracil derivatives.J. Org. Chem. 55, 4928 (1990).

    Article  CAS  Google Scholar 

  7. (a) Ryu, E. K. and MacCoss, M.: New procedure for the chlorination of pyrimidine and purine nucleosides.J. Org. Chem. 46, 2819 (1981). (b) Ryu, E. K. and Kim, J. N.: The oxidative chlorination of pyrimidine and purine bases, and nucleosides using acyl chloride-dimethylformamide-m-chloroperbenzoic acid system.Nucleosides and Nucleotides.8, 43 (1989).

    Article  CAS  Google Scholar 

  8. (a) Chung, K. H. Kim, K. M. Kim, J. N. and Ryu, E. K.: Oxidative chlorination of acetanilides with hydrogen chloride/m-chloroperbenzoic acid /N,N-dimethyl-formamide system.Synthetic Commun.,21, 1917 (1991). (b) Chung, K. H. Kim, H. J. Kim, H. R. and Ryu, E. K.: Oxidative chlorination of phenols with hydrogen chloride/m-chloroperbenzoic acid/N,N-dimethylformamide system,Synthetic Commun.,20, 2991 (1990).

    Article  CAS  Google Scholar 

  9. Chang, P. K. and Welch, A. D.: Iodination of 2′-deoxycytidine and related substances.J. Med. Chem. 6, 428 (1963).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Pharmacy, Chungbuk National University, Cheongju, 360-763, Chungbuk, Korea

    Chang Ho Hwang, Jung Sup Park & Jeong Hee Won

  2. Korea Research Institute of Chemical Technology, Daedeog-Danji, 305-606, Daejeon, Korea

    Jae Nyoung Kim & Eung K. Ryu

Authors
  1. Chang Ho Hwang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jung Sup Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jeong Hee Won
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jae Nyoung Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Eung K. Ryu
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hwang, C.H., Park, J.S., Won, J.H. et al. The oxidative iodination of pyrimidine bases and their nucleosides using iodine/dimethylformamide/ m-chloroperbenzoic acid. Arch. Pharm. Res. 15, 69–72 (1992). https://doi.org/10.1007/BF02973987

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02973987

Keywords

Search

Navigation