Synthesis and immunostimulatory activity of 8-substituted amino 9-benzyladenines as potent Toll-like receptor 7 agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 17, 2006, Pages 4559-4563

  Jin, Guangyi ^a   Wu, Christina C N ^a   Tawatao, Rommel I ^a   Chan, Michael ^a   Carson, Dennis A ^a   Cottam, Howard B ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

8 Substituted aminoadenines; Innate immune response; Interferon inducers; Toll like receptor agonists

Indexed keywords

ADENINE DERIVATIVE; HORMONE RECEPTOR STIMULATING AGENT; IMIQUIMOD; INTERFERON; MORPHOLINE DERIVATIVE; RESIQUIMOD; TOLL LIKE RECEPTOR 7;

ANIMAL CELL; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IMMUNOSTIMULATION; INTERFERON PRODUCTION; MOUSE; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ADENINE; AMINATION; HUMANS; LEUKOCYTES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TOLL-LIKE RECEPTOR 7;

EID: 33746222920     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.06.017     Document Type: Article

References (29)

1. Nagahara K., Anderson J.D., Kini G.D., Dalley N.K., Larson S.B., Smee D.F., Jin A., Sharma B.S., Jolley W.B., Robins R.K., and Cottam H.B. J. Med. Chem. 33 (1990) 407
2. Bontems R.J., Anderson J.D., Smee D.F., Jin A., Alaghamandan H.A., Sharma B.S., Jolley W.B., Robins R.K., and Cottam H.B. J. Med. Chem. 33 (1990) 2174
3. Michael M.A., Cottam H.B., Smee D.F., Robins R.K., and Kini G.D. J. Med. Chem. 36 (1993) 3431
4. Smee D.F., Alaghamandan H.A., Gilbert J., Burger R.A., Jin A., Sharma B.S., Ramasamy K., Revankar G.R., Cottam H.B., et al. Antimicrob. Agents Chemother. 35 (1991) 152
5. Girgis N.S., Michael M.A., Smee D.F., Alaghamandan H.A., Robins R.K., and Cottam H.B. J. Med. Chem. 33 (1990) 2750
6. Smee D.F., Huffman J.H., Gessaman A.C., Huggins J.W., and Sidwell R.W. Antiviral Res. 15 (1991) 229
7. Smee D.F., Alaghamandan H.A., Jin A., Sharma B.S., and Jolley W.B. Antiviral Res. 13 (1990) 91
8. Smee D.F., Alaghamandan H.A., Cottam H.B., Sharma B.S., Jolley W.B., and Robins R.K. Antimicrob. Agents Chemother. 33 (1989) 1487
9. Smee D.F., Alaghamandan H.A., Ramasamy K., and Revankar G.R. Antiviral Res. 26 (1995) 203
10. Reitz A.B., Goodman M.G., Pope B.L., Argentieri D.C., Bell S.C., Burr L.E., Chourmouzis E., Come J., Goodman J.H., et al. J. Med. Chem. 37 (1994) 3561
11. Lee J., Chuang T.-H., Redecke V., She L., Pitha P.M., Carson D.A., Raz E., and Cottam H.B. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 6646
12. Isobe Y., Kurimoto A., Tobe M., Hashimoto K., Nakamura T., Norimura K., Ogita H., and Takaku H. J. Med. Chem. 49 (2006) 2088
13. Kurimoto A., Tobe M., Ogita H., Ogino T., Takaku H., Ichii S., Kawakami H., and Isobe Y. Chem. Pharm. Bull. 52 (2004) 466
14. Kurimoto A., Ogino T., Ichii S., Isobe Y., Tobe M., Ogita H., Takaku H., Sajiki H., Hirota K., and Kawakami H. Bioorg. Med. Chem. 12 (2004) 1091
15. Horsmans Y., Berg T., Desager J.-P., Mueller T., Schott E., Fletcher S.P., Steffy K.R., Bauman L.A., Kerr B.M., and Averett D.R. Hepatology (Hoboken, NJ, United States) 42 (2005) 724
16. Lee J., Wu C.C.N., Lee K.J., Chuang T.-H., Katakura K., Liu Y.-T., Chan M., Tawatao R., Chung M., Shen C., Cottam H.B., Lai M.M.C., Raz E., and Carson D.A. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 1828
17. Tran H., Moreno G., and Shumack S. Expert Opin. Pharmacother. 5 (2004) 427
18. Amlie-Lefond C., Paz D.A., Connelly M.P., Huffnagle G.B., Dunn K.S., Whelan N.T., and Whelan H.T. J. Allergy Clin. Immunol. 116 (2005) 1334
19. Holmes R.E., and Robins R.K. J. Am. Chem. Soc. 87 (1965) 1772
20. Young R.C., Jones M., Milliner K.J., Rana K.K., and Ward J.G. J. Med. Chem. 33 (1990) 2073
21. Janeba Z., Holy A., and Masojidkova M. Collect. Czech. Chem. Commun. 66 (2001) 517
22. de Ligt R.A.F., van der Klein P.A.M., von Frijtag Drabbe Kunzel J.K., Lorenzen A., Ait El Maate F., Fujikawa S., van Westhoven R., van den Hoven T., Brussee J., and Ijzerman A.P. Bioorg. Med. Chem. 12 (2004) 139
23. Kelley J.L., McLean E.W., Linn J.A., Krochmal M.P., Ferris R.M., and Howard J.L. J. Med. Chem. 33 (1990) 196
24. 2. The IFN-α level in the supernatants was measured by Luminex (Austin, TX) using the Beadlyte Human MultiCytokine kit (Upstate, Charlottesville, VA), according to the manufacturer's instructions. Results presented in the table are averages of data composited from four different donors.
25. 3: C, 56.97; H, 6.19; N, 23.45%. Found: C, 56.59; H, 6.29; N, 23.06%.
26. 2O: C, 58.05; H, 6.54; N, 23.90%. Found: C, 58.45; H, 6.44; N, 23.64%.
27. 2O: C, 56.63; H, 6.55; N, 22.02%. Found: C, 57.01; H, 6.42; N, 22.22%.
28. 2O: C, 58.45; H, 6.81; N, 22.73%. Found: C, 58.51; H, 6.85; N, 22.51%.
29. 50.