Abstract
A convenient method has been developed for the synthesis of 9-allyloxymethylguanine. The direct alkylation of the trimethylsilyl derivative of guanine allyloxymethyl chloride gives a 64% yield of 9- and 7-allyloxymethylguanine (3∶1). A mixture of 9- and 7-allyloxymethyl-N-acetylguanine (7∶4) can be obtained in 56% yield by the condensation of diacetylguanine with allyloxymethyl acetate in dimethyl sulfoxide in the presences of p-toluenesulfonic acid.
Similar content being viewed by others
References
H. L. Schaeffer, L. Beauchamp, P. De Miranda, G. B. Elion, D. L. Bauer, and P. Collins, Nature, 272, 583 (1978).
Y.-C. Cheng, S. P. Grill, G. E. Dutschman, K. Nakayama, and K. F. Bastow, J. Biol. Chem., 258, 12460 (1983).
A. Larsson and P.-Z. Tao, Antimicrob. Agents Chemother., 25, 524 (1984).
J. D. Karkas, W. T. Ashton, L. F. Canning, R. Liou, J. Germershausen, R. Bostedor, B. Arison, A. K. Field, and R. L. Tolman, J. Med. Chem., 29, 842 (1986).
G. Abele, B. Eriksson, J. Harmenberg, and B. Wahren, Antimicrob. Agents Chemother., 32, 1137 (1988).
A. A. Ozerov, M. S. Novikov, A. K. Brel', O. T. Andreeva, G. V. Vladyko, E. I. Boreko, L. V. Korobchenko, and S. G. Vervetchenko, Khim.-Farm. Zh., 25, 44 (1991).
J. C. Martin, C. A. Dvorak, D. F. Smee, T. R. Matthews, and J. P. H. Verheyden, J. Med. Chem., 26, 759 (1983).
W. T. Ashton, L. F. Canning, G. F. Reynolds, R. L. Tolman, J. D. Karkas, R. Liou, M.-E. M. Davies, C. M. De Witt, H. C. Perry, and A. K. Field, J. Med. Chem., 28, 926 (1985).
H. Matsumoto, C. Kaneko, K. Yamada, T. Takeuchi, T. Mori, and Y. Mizuno, Chem. Pharm. Bull., 36, 1153 (1988).
J. C. Martin, D. C. P. McGee, G. A. Jeffrey, D. W. Hobbs, D. F. Smee, T. R. Matthews, and J. P. H. Verheyden, J. Med. Chem., 29, 1384 (1986).
Yu. V. Pokonova, Chemistry and Technology of Halogenoethers [in Russian], Leningrad University, Leningrad (1982).
Kh. A. Khazhoka and V. D. Shatts, Khim.-Farm. Zh., 23, 1516 (1989).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1109–1113, August, 1993.
Rights and permissions
About this article
Cite this article
Ozerov, A.A., Brel', A.K. Synthesis of a new potential antiviral agent — 9-allyloxymethylguanine. Chem Heterocycl Compd 29, 945–948 (1993). https://doi.org/10.1007/BF00534275
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00534275