Cyclic nucleotide phosphodiesterase type 4 inhibitors: Evaluation of pyrazolo[1,5-a]-1,3,5-triazine ring system as an adenine bioisostere

European Journal of Medicinal Chemistry

Volumn 43, Issue 4, 2008, Pages 816-829

  Raboisson, Pierre ^a,c   Schultz, Dominique ^a   Muller, Christian ^b   Reimund, Jean Marie ^b   Pinna, Guillaume ^b   Mathieu, Romain ^a   Bernard, Philippe ^d   Do, Quoc Tuan ^d   DesJarlais, Renee L ^c   Justiano, Hélène ^b   Lugnier, Claire ^b   Bourguignon, Jean Jacques ^a  

^a Laboratoire de Pharmacochimie   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c TIBOTEC BVBA   (Belgium)

^d GreenPharma SA   (France)

Author keywords

Bioisostere; Inflammation; Phosphodiesterase; Pyrazolo 1,5 a 1,3,5 triazines; TNF ; Type 4

Indexed keywords

2 TRIFLUOROMETHYL 8 (2 METHOXYBENZYL) 4 (N METHYLAMINO)PYRAZOLO[1,5 A] 1,3,5 TRIAZINE; 8 (2 METHOXYBENZYL) 4 (N METHYLAMINO) 2 N PROPYLPYRAZOLO[1,5 A] 1,3,5 TRIAZINE; PHOSPHODIESTERASE IV INHIBITOR; PYRAZOLO[1,5 A] 1,3,5 TRIAZINE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; CYTOKINE RELEASE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MONONUCLEAR CELL;

ADENINE; CYCLIC NUCLEOTIDE PHOSPHODIESTERASES, TYPE 4; ENZYME INHIBITORS; HUMANS; HYDROCARBONS, FLUORINATED; LIPOPOLYSACCHARIDES; METHYLAMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PALLADIUM; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 41249090531     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.05.016     Document Type: Article

References (36)

1. Souness J.E., Aldous D., and Sargent C. Immunopharmacology 47 (2000) 127-162
2. Teixeira M.M., Gristwood R.W., Cooper N., and Hellewell P.G. Trends Pharmacol. Sci. 18 (1997) 164-170
3. Duplantier A.J., and Cheng J.B. Annu. Rep. Med. Chem. 29 (1994) 73-81
4. Huang Z., Ducharme Y., Macdonald D., and Robichaud A. Curr. Opin. Chem. Biol. 5 (2001) 432-438
5. Torphy T.J. Am. J. Respir. Crit. Care Med. 157 (1998) 351-370
6. Robichaud A., Savoie C., Stamatiou P.B., Tattersall F.D., and Chan C.C. Neuropharmacology 40 (2001) 262-269
7. Zhang H.T., Huang Y., Jin S.L., Frith S.A., Suvarna N., Conti M., and O'Donnell J.M. Neuropsychopharmacology 27 (2002) 587-595
8. Torphy T.J., Barnette M.S., Underwood D.C., Griswold D.E., Christensen S.B., Murdoch R.D., Nieman R.B., and Compton C.H. Pulm. Pharmacol. Ther. 12 (1999) 131-135
9. Piaz V.D., and Giovannoni M.P. Eur. J. Med. Chem. 35 (2000) 463-480
10. Conti M., and Jin S.-L.C. Prog. Nucleic Acid Res. Mol. Biol. 63 (2000) 1-38
11. Robichaud A., Stamatiou P.B., Jin S.-L.C., Lachance N., MacDonald D., Laliberté F., Liu S., Huang Z., Conti M., and Chan C.-C. J. Clin. Invest. 110 (2002) 1045-1052
12. Giembycz M.A. Trends Pharmacol. Sci. 23 (2002) 548
13. Pascal Y., Andrianjara C.R., Auclair E., Avenel N., Bertin B., Calvet A., Feru F., Lardon S., Moodley I., Ouagued M., Payne A., Pruniaux M.P., and Szilagyi C. Bioorg. Med. Chem. Lett. 10 (2000) 35-38
14. Tulshian D., Czarniecki M., Doll R.J., and Ahn H.-S. J. Med. Chem. 36 (1993) 1210-1220
15. Bourguignon J.-J., Désaubry L., Raboisson P., Wermuth C.G., and Lugnier C. J. Med. Chem. 40 (1997) 1768-1770
16. Boichot E., Wallace J.L., Germain N., Corbel M., Lugnier C., Lagente V., and Bourguignon J.-J. J. Pharmacol. Exp. Ther. 292 (2000) 647-653
17. Hichami A., Boichot E., Germain N., Legrand A., Moodley I., and Lagente V. Eur. J. Pharmacol. 291 (1995) 91-97
18. Burger A. Prog. Drug Res. 37 (1991) 287-371
19. Olesen P.H. Curr. Opin. Drug Discov. Devel. 4 (2001) 471-478
20. Raboisson P., Schultz D., Baurand A., Cazenave J.-P., Gachet C., Spiess B., and Bourguignon J.-J. J. Org. Chem. 67 (2002) 8063-8071
21. Sybyl 6.8, Tripos, Inc., 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA.
22. Clark M., Cramer III R.D., and Van Opdenbosch N. J. Comp. Chem. 10 (1989) 982-1012
23. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902-3909
24. Mopac: Quantum Chemistry Program Exchange, Creative Arts Building 181, Indiana University, Bloomington, Indiana 47405, USA. Phone: +1 (812) 855-4784; Fax: +1 (812) 855-5678. As a service to the scientific community, QCPE programs (such as MOPAC, FORTICON 8, and GAUSSIAN 80) are distributed on a not-for-profit basis.
25. Laboratory for Molecular Graphics and Theoretical Modeling of the College of Pharmacy of the University of Texas at Austin USA.
26. Press W.H., Flannery B.P., Teukolsky S.A., and Vetterling W.T. Numerical recipes in C. The Art of Scientific Computing (1988), Cambridge University Press CONJUGATE GRADIENTS (p. 301), SIMPLEX (p. 312), and BFGS (p. 324
27. Powell M.J.D. Restart procedures for the conjugate gradient method. Math. Program. 12 (1977) 241-254
28. Brickmann J., Exner T.E., Keil M., and Marhöfer R.J. J. Mol. Model. 6 (2000) 328-340
29. Heiden W., Moeckel G., and Brickmann J. J. Comput. Aided Mol. Des. 7 (1993) 503-514
30. Raboisson P., Lugnier C., Muller C., Reimund J.-M., Schultz D., Pinna G., Lebec A., Bassaran H., Desaubry L., Gaudiot F., Seloum M., and Bourguignon J.-J. Eur. J. Med. Chem. 2003 38 (2003) 199-214
31. Raboisson P., Schultz D., Lugnier C., and Bourguignon J.-J. Tetrahedron Lett. 43 (2002) 9501-9503
32. Lugnier C., Schoeffter P., Le Bec A., Strouthou E., and Stoclet J.-C. Biochem. Pharmacol. 35 (1986) 1743-1751
33. Lugnier C., and Schini V. Biochem. Pharmacol. 39 (1990) 75-84
34. Keravis T.M., Wells J.N., and Hardman J.G. Biochim. Biophys. Acta 613 (1980) 116-129
35. Boyum A. Scand. J. Clin. Lab. Invest. Suppl. 97 (1968) 77-89
36. Reimund J.-M., Wittersheim C., Dumont S., Muller C.D., Kenney J.S., Baumann R., Poindron P., and Duclos B. Gut 39 (1996) 684-689