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Purine Nucleoside Analogs. 12. Synthesis of Novel 8,9-Disubstituted Guanine Derivatives by S-Alkylation of 2-Acetamido-9-(2-acetoxyethoxymethyl)-6-oxo-8-thioxopurine

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Abstract

S-Alkylation of 2-acetamido-9-(2-acetoxyethoxymethyl)-6-oxo-8-thioxopurine was used to synthesize its novel S- and N(7)-substituted derivatives. We have established the effect of the structure of the alkylating agent on the reaction conditions and its regioselectivity. We have shown that the synthesized guanine derivatives can be modified further.

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REFERENCES

  1. M. Madre, N. Panchenko, A. Golbraikh, R. Zhuk, U. K. Pandit, J. Geenevasen, and G.-J. Koomen, Collect. Czech. Chem. Commun., 64, 685 (1999).

    Google Scholar 

  2. C. Simons, Nucleoside Mimetics: Their Chemistry and Biological Properties, Gordon and Breach Sci. Publ., Amsterdam (2001), p. 155.

    Google Scholar 

  3. W.-V. Meister, S. Lindau, A. L. Hauser, C. Bohley, U. Gromann, S. Naumann, M. Madre, L. Kovalenko, G. Bischoff, R. Zhuk, and S. Hoffmann, J. Biomol. Struct. & Dyn., 18, 385 (2000).

    Google Scholar 

  4. M. J. Robins, P. W. Hatfield, J. Balzarini, and E. De Clercq, J. Med. Chem., 27, 1486 (1984).

    Google Scholar 

  5. T.-Sh. Lin, J.-Ch. Cheng, K. Ishiguro, and A. C. Sartorelli, J. Med. Chem., 28, 1194 (1985).

    Google Scholar 

  6. M. Ikaunieks and M. Madre, J. Chem. Res. (S), 5, 226 (2002).

    Google Scholar 

  7. M. A. Michael, H. B. Cottam, D. F. Smee, R. K. Robins, and G. D. Kini, J. Med. Chem., 36, 3431 (1993).

    Google Scholar 

  8. A. B. Reitz, M. G. Goodman, B. L. Pope, D. C. Argentieri, S. C. Bell, L. E. Burr, E. Chourmouzis, J. Come, J. H. Goodman, D. H. Klaubert, B. E. Maryanoff, M. E. McDonnell, M. S. Rampulla, M. R. Schott, and R. Chen, J. Med. Chem., 37, 3561 (1994).

    Google Scholar 

  9. M. Madre, R. Zhuk, and B. Golankiewicz, Polish J. Chem., 72, 2242 (1992).

    Google Scholar 

  10. M. A. Madre, R. A. Zhuk, and M. Yu. Lidaks, Bioorg. Khim., 17, 1516 (1991).

    Google Scholar 

  11. M. Ubasawa, H. Takashima, and K. Sekiya, Nucleosides & Nucleotides, 17, 2241 (1998).

    Google Scholar 

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV-1006

    M. Ikaunieks & M. Madre

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  1. M. Ikaunieks
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  2. M. Madre
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Ikaunieks, M., Madre, M. Purine Nucleoside Analogs. 12. Synthesis of Novel 8,9-Disubstituted Guanine Derivatives by S-Alkylation of 2-Acetamido-9-(2-acetoxyethoxymethyl)-6-oxo-8-thioxopurine. Chemistry of Heterocyclic Compounds 39, 244–249 (2003). https://doi.org/10.1023/A:1023732827820

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  • DOI: https://doi.org/10.1023/A:1023732827820

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