Discovery of 8-hydroxyadenines as a novel type of interferon inducer

Journal of Medicinal Chemistry

Volumn 45, Issue 25, 2002, Pages 5419-5422

  Hirota, Kosaku ^a   Kazaoka, Kazunori ^a   Niimoto, Itaru ^a   Kumihara, Hiroshi ^a   Sajiki, Hironao ^a   Isobe, Yoshiaki ^b   Takaku, Haruo ^b   Tobe, Masanori ^b   Ogita, Haruhisa ^b   Ogino, Tetsuhiro ^c   Ichii, Shinji ^c   Kurimoto, Ayumu ^c   Kawakami, Hajime ^c  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b JAPAN ENERGY CORPORATION   (Japan)

^c DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

9 BENZYL 8 HYDROXYADENINE; AMINO ACID DERIVATIVE; INTERFERON INDUCING AGENT; LEAD; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; IN VITRO STUDY; MOUSE; NONHUMAN;

ADENINE; ADMINISTRATION, ORAL; ANIMALS; INTERFERON INDUCERS; MICE; SPLEEN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037028041     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0203581     Document Type: Article

References (26)

1. Wang, Q. M.; Heinz, B. A. Recent advances in prevention and treatment of hepatitis C virus infections. Prog. Drug. Res. 2000, 55, 1-32.
2. Rönnblom, L. E.; Janson, E. T.; Perers, A.; Öberg, K. E.; Alm, G. V. Characterization of anti-interferon-α antibodies appearing during recombinant interferon-α2a treatment. Clin. Exp. Immunol. 1992, 89, 330-335.
3. Wierenga, W. Interferon inducers. Annu. Rep. Med. Chem. 1982, 17, 151-161.
4. Krueger, R. F.; Mayer, G. D. Tilorone Hydrochloride: An Orally Active Antiviral Agent. Science 1970, 169, 1213-1214.
5. Siminoff, P.; Bernard, A. M.; Hursky, V. S.; Price, K. E. BL-20803, a new, low-molecular-weight interferon inducer. Antimicrob. Agents Chemother. 1973, 3, 742-743.
6. Gláz, E. T.; Szolgay, E.; Stöger, I.; Tálas, M. Antiviral activity and induction of interferon-like substance by quinacrine and acranil. Antimicrob. Agents Chemother. 1973, 3, 537-541.
7. Hoffman, W. W.; Korst, J. J.; Niblack, J. F.; Cronin, T. H. N,N-dioctadecyl-N′,N′-bis(2-hydroxyethyl)propanediamine: Antiviral activity and interferon stimulation in mice. Antimicrob. Agents Chemother. 1973, 3, 498-502.
8. Nichol, F. R.; Weed, S. D.; Underwood, G. E. Stimulation of murine interferon by a substituted pyrimidine. Antimicrob. Agents Chemother. 1976, 9, 433-439.
9. Tamm, I.; Sehgal, P. B. A Comparative study of the effects of certain halogenated benzimidazole ribosides on RNA synthesis, cell proliferation, and interferon production. J. Exp. Med. 1977, 145, 344-356.
10. Taylor, J. L.; Schoenherr, C. K.; Grossberg, S. E. High-yield interferon induction by 10-carboxymethyl-9-acridanone in mice and hamsters. Antimicrob. Agents Chemother. 1980, 18, 20-26.
11. Wierenga, W.; Skulnick, H. I.; Stringfellow, D. A.; Weed, S. D.; Renis, H. E.; Eidson, E. E. 5-Substituted 2-amino-6-phenyl-4(3H)-pyrimidinones. Antiviral- and interferon-inducing agents. J. Med. Chem. 1980, 23, 237-239.
12. Weeks, C. E.; Reiter, M. J. Antiviral/immunomodulator R-837 induces alpha interferon in mice. J. Invest. Dermatol. 1989, 93, 584.
13. Dockrell, D. H.; Kinghorn, G. R. Imiquimod and resiquimod as novel immunomodulators. J. Antimicrob. Chemother. 2001, 48, 751-755.
14. Weeks, C. E.; Gibson, S. J. Induction of interferon and other cytokines by imiquimod and its hydroxylated metabolite R-842 in human blood cells in vitro. J. Interferon Res. 1994, 14, 81-85.
15. Tomai, M. A.; Gibson, S. J.; Imbertson, L. M.; Miller, R. L.; Myhre, P. E.; Reiter, M. J.; Wagner, T. L.; Tamulinas, C. B.; Beaurline, J. M.; Gerster, J. F.; Horton, V. L. Immunomodulating and antiviral activities of the imidazoquinoline S-28463. Antiviral Res. 1995, 28, 253-264.
16. (a) Holmes, R. E.; Robins, R. K. Purine nucleosides. VII. Direct bromination of adenosine, deoxyadenosine, guanosine, and related purine nucleosides. J. Am. Chem. Soc. 1964, 86, 1242-1245.
17. (b) Hirota, K.; Kitade, Y.; Kanbe, Y.; Maki, Y. Convenient method for the synthesis of C-alkylated purine nucleosides: Palladium-catalyzed cross-coupling reaction of halogenopurine nucleosides with trialkylaluminums. J. Org. Chem. 1992, 57, 5268-5270.
18. (c) Altman, J.; Ben-Ishai, D. Acylation of nitrogen heterocycles. II. Carbobenzoxylation of substituted adenines under the conditions of the Schotten-Baumann reaction. Chem. Pharm. Bull. 1968, 5, 679-682.
19. (d) Robins, R. K. Potential purine antagonists. XV. Preparation of some 6,8-disubstituted purines. J. Am. Chem. Soc. 1958, 80, 6671-6679.
20. (e) Lin, T.-S.; Cheng, J.-C.; Ishiguro, K.; Sartorelli, A. C. 8-Substituted guanosine and 2′-deoxyguanosine derivatives as potential inducers of the differentiation of friend erythroleukemia cells. J. Med. Chem. 1985, 28, 1194-1198.
21. (f) Koda, R. T.; Biles, J. A.; Wolf, W. Synthesis of some iodopurine derivatives. J. Pharm. Sci. 1968, 57, 2056-2061.
22. Fujii, T.; Saito, T. Purines. XIII. Ring opening of 3-alkyladenines with carbobenzoxy chloride: Transformation into 8-hydroxylated adenines. Chem. Pharm. Bull. 1973, 21, 1954-1959.
23. Hirota, K.; Kazaoka, K.; Niimoto, I.; Sajiki, H. Novel and efficient synthesis of 8-oxoadenine derivatives. Heterocycles 2001, 55, 2279-2282.
24. (a) Watanabe, Y.; Kawade, Y. In Lymphokines and Interferons: A Practical Approach; Clemens, M. J.; Morris, A. G. Gearing, A. J. H., Eds.; IRL Press: Oxford, 1987; pp 1-14.
25. (b) Pestka, S. Method in Enzymology, Pestka, S., Ed.; Academic Press: New York, 1986; Vol. 119, pp 14-23.
26. Hemmi, H.; Kaisho, T.; Takeuchi, O.; Sato, S.; Sanjo, H.; Hoshino, K.; Horiuchi, T.; Tomizawa, H.; Takeda, K.; Akira, S. Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nature Immunol. 2002, 3, 196-200.