Design, synthesis and structure-activity relationships of a series of 9-substituted adenine derivatives as selective phosphodiesterase type-4 inhibitors

European Journal of Medicinal Chemistry

Volumn 38, Issue 2, 2003, Pages 199-214

  Raboisson, Pierre ^a,c   Lugnier, Claire ^b   Muller, Christian ^b   Reimund, Jean Marie ^b   Schultz, Dominique ^a   Pinna, Guillaume ^b   Le Bec, Alain ^b   Basaran, Hélène ^b   Desaubry, Laurent ^a   Gaudiot, François ^a   Seloum, Mohamed ^a   Bourguignon, Jean Jacques ^a  

^a Laboratoire de Pharmacochimie   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c JOHNSON AND JOHNSON   (United States)

Author keywords

Adenine; Inflammation; Phosphodiesterase; TNF ; Type 4

Indexed keywords

2 IODO 9 (2 METHOXYBENZYL) 6 N METHYLADENINE; 9 (2 FLUOROBENZYL) 6 N METHYL 2 TRIFLUOROMETHYLADENINE; 9 (2 METHOXYBENZYL) 6 N METHYL 2 PROPYLADENINE; 9 (2 METHOXYBENZYL) 6 N METHYL 2 TRIFLUOROMETHYLADENINE; 9 BENZYL 6 N METHYL 2 PROPYLADENINE; ADENINE DERIVATIVE; FUNCTIONAL GROUP; ISOENZYME; PHOSPHODIESTERASE IV; PHOSPHODIESTERASE IV INHIBITOR; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0037293780     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(02)01446-0     Document Type: Article

References (38)

1. Torphy J.T. Am. J. Respir. Crit. Care Med. 157:1998;351-370.
2. Juilfs D.M., Soderling S., Burns F., Beavo J.A. Rev. Physiol. Biochem. Pharmacol. 135:1999;67-104.
3. Mueller T., Engels P., Fozard J.R. Trends Pharmacol. Sci. 17:1996;294-298.
4. Doherty A.M. Curr. Opin. Chem. Biol. 3:1999;466-473.
5. Burnouf C., Pruniaux M.-P., Szilagyi C.M. Annu. Rep. Med. Chem. 33:1998;91-109.
6. Bielekova B., Lincoln A., McFarland H., Martin R. J. Immunol. 164:2000;1117-1124.
7. Teixeira M.M., Gristwood R.W., Cooper N., Hellewell P.G. Trends Pharmacol. Sci. 18:1997;164-170.
8. Souness J.E., Aldous D., Sargent C. Immunopharmacology. 47:2000;127-162.
9. R.B. Nieman, O. Fischer, R.J. Ami, ALA/ATS International Conference, Chicago, IL, 1998, Poster B55.
10. Nell H., Leichtl S., Rathgeb F., Neuhauser M., Bardin P.G., Louw C. Am. J. Respir. Crit. Care Med. 161:2000;A505. abstract.
11. Torphy T.J. Am. J. Respir. Crit. Care Med. 157:1998;351-370.
12. Robichaud A., Savoie C., Stamatiou P.B., Tattersall F.D., Chan C.C. Neuropharmacology. 40:2001;262-269.
13. Cavalla D., Frith R. Curr. Med. Chem. 2:1995;561-572.
14. Kelley J.L., Sokoro F.E. J. Med. Chem. 29:1986;1133-1134.
15. Willard M., Misslin R., Vogel E., Desaubry D., Wermuth C.G., Bourguignon J.-J. Pharmacol. Biochem. Behav. 35:1989;85-88.
16. Bourguignon J.-J., Désaubry L., Raboisson P., Wermuth C.G., Lugnier C. J. Med. Chem. 40:1997;1768-1770.
17. Boichot E., Wallace J.L., Germain N., Corbel M., Lugnier C., Lagente V., Bourguignon J.-J. J. Pharmacol. Exp. Ther. 292:2000;647-653.
18. Hichami A., Boichot E., Germain N., Legrand A., Moodley I., Lagente V. Eur. J. Pharmacol. 291:1995;91-97.
19. Mackenzie G., Wilson H.A., Shaw G., Ewing D. J. Chem. Soc. Perkin Trans. 1:(9):1988;2541-2546.
20. Cusack N.J., Shaw G., Logemann F.I. J. Chem. Soc. Perkin Trans. 1:(10):1980;2316-2321.
21. Thomas H.J., Avery L.N., Brockman R.W., Montgomery J.A. J. Med. Chem. 30:1987;431-434.
22. Imai K., Marumoto R., Kobayashi K., Yoshioka Y., Toda J., Honjo M. Chem. Pharm. Bull. 19:1971;576-586.
23. Kelley J.L., Linn J.A., Selway J.W.T. J. Med. Chem. 30:1989;218-224.
24. Montgomery J.A., Temple C. J. Am. Chem. Soc. 83:1961;630-635.
25. H. Bader, Y.H. Chiang, US Patent, 4 405,781, (1983). H. Bader, Y.H. Chiang, Chem. Abstr. (100) (1984) 6549r.
26. Pérez-Pérez M.-J., Rozenski J., Busson R., Herdewijn P. J. Org. Chem. 60:1995;1531-1537.
27. Ciapetti P., Soccolini F., Taddei M. Tetrahedron. 53:1997;1167-1176.
28. Nair V., Richardson S.G. Synthesis. 8:1982;670-672.
29. Cristalli G., Eleuteri A., Vittori S., Volpini R., Lohse M.J., Koltz K.-N. J. Med. Chem. 35:1992;2362-2368.
30. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483.
31. Greenber S.M., Ross L.O., Robins R.K. J. Org. Chem. 24:1959;1314-1317.
32. Elion G.B. J. Org. Chem. 27:1962;2478-2491.
33. Gough G., Maguire M.H. J. Med. Chem. 10:1967;475-478.
34. Lugnier C., Schoeffter P., Le Bec A., Strouthou E., Stoclet J.-C. Biochem. Pharmacol. 35:1986;1743-1751.
35. Keravis T.M., Wells J.N., Hardman J.G. Biochem. Biophys. Acta. 613:1980;116-129.
36. Boyum A. Scand. J. Clin. Lab. Invest. (Suppl. 97):1968;77-89.
37. Reimund J.-M., Wittersheim C., Dumont S., Muller C.D., Kenney J.S., Baumann R., Poindron P., Duclos B. Gut. 39:1996;684-689.
38. White J.D., Choi Y. Org. Lett. 2:2000;2373-2376.