Abstract
New 9-(aryloxyalkyl) derivatives of adenine have been prepared by alkylation of adenine with tosylates, bromides, and α-chloro ethers containing terminal aromatic fragments in anhydrous DMF in the presence of potassium carbonate. The compounds of the 9-(2-phenoxyethyl)adenine series appear to be highly reactive against cytomegaloviruses of mankind in vitro, while derivatives of 9-(2-benzyloxyethyl)adenine demonstrate anti-HIV-1 activity. Compounds with shorter or longer chains, and also compounds which do not have aromatic fragments at the ends of the chains, do not possess antiviral activity.
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REFERENCES
E. De Clercq, J. Deschamps, P. De Somer, and A. Holy, Science, 200, 563 (1978).
S. Hayashi, S. Phadtaro, J. Zemlicka, M. Matsukara, H. Mitsuya, and S. Broder, Proc. Nat. Acad. Sci. USA, 85, 6127 (1988).
A. A. Ozerov, Thesis for Doctor of Chem. Sci., Volgograd, 1994.
H. Tanaka, H. Takashima, M. Ubasawa. K. Sekiya, N. Inoue, M. Baba, S. Shigeta, R. T. Walker, E. De Clercq, and T. Miyasaka, J. Med. Chem., 38, 2860 (1995).
A. Mai, M. Artico, G. Sbardella, S. Massa, A. G. Loi, E. Tramontano, P. Seano, and P. La Colla, J. Med. Chem., 38, 3258 (1995).
J. Balzarini and E. De Clercq, J. Biol. Chem., 266, 8686 (1991).
T. P. Ozerova, A. K. Brel', and M. S. Novikov, Vestn. Volgograd. Med. Akad., 54, No. 4, 36 (1998).
A. A. Ozerov, M. S. Novikov, and A. K. Brel', Khim. Geterotsikl. Soedin., 82 (1999).
T. P. Ozerova, Thesis for Candidate of Chem. Sci, Volgograd, 2000.
V. I. No, G. M. Butov, and V. M. Mokhov, Zh. Org. Khim., 35, 149 (1999).
Yu. V. Pokonova, Chemistry and Technology of Halo Ethers [in Russian], Leningrad State University, Leningrad, 1982.
Z. Sun and R. S. Hosmane, Synth. Commun., 31, 549 (2001).
D. H. Shepp, P. S. Dandliker, P. de Miranda, T. C. Burnette, D. M. Cederberg, L. E. Kirk, and J. D. Meyers, Ann. Intern. Med., 103, 368 (1985).
R. Snoek, I. Sakuma, E. De Clercq, I. Rosenberg, and A. Holy, Antimicrob. Agents Chemother., 32, 1839 (1988).
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Petrov, V.I., Ozerov, A.A., Novikov, M.S. et al. 9-(2-Aryloxyethyl) Derivatives of Adenine - a New Class of Non-nucleosidic Antiviral Agents. Chemistry of Heterocyclic Compounds 39, 1218–1226 (2003). https://doi.org/10.1023/B:COHC.0000008270.32235.2b
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DOI: https://doi.org/10.1023/B:COHC.0000008270.32235.2b