Rhodanine derivatives as novel inhibitors of PDE4

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 6, 2008, Pages 2032-2037

  Irvine, Mark W ^a   Patrick, Graham L ^a   Kewney, Justin ^b   Hastings, Stuart F ^b   MacKenzie, Simon J ^b  

^a UNIVERSITY OF THE WEST OF SCOTLAND   (United Kingdom)

^b Scottish Biomedical   (United Kingdom)

Author keywords

Asthma; COPD; PDE4 inhibitor; Phosphodiesterase 4; Rhodanine

Indexed keywords

CILOMILAST; PHOSPHODIESTERASE IV; PHOSPHODIESTERASE IV INHIBITOR; RHODAMINE; ROFLUMILAST; ROLIPRAM; THIOHYDANTOIN DERIVATIVE;

ARTICLE; BINDING SITE; CHEMICAL MODIFICATION; DENSITY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; IN VITRO STUDY; NONHUMAN; STRUCTURE ACTIVITY RELATION;

CYCLIC NUCLEOTIDE PHOSPHODIESTERASES, TYPE 4; HUMANS; MOLECULAR STRUCTURE; PHOSPHODIESTERASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOHYDANTOINS;

EID: 40749100178     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.117     Document Type: Article

References (41)

1. Torphy T.J. Am. J. Respir. Crit. Care Med. 157 (1998) 351
2. Souness J.E., Aldous D., and Sargent C. Immunopharmacology 47 (2000) 127
3. Cavalla D., and Frith R. Curr. Med. Chem. 2 (1995) 561
4. Lombardo L.J. Curr. Pharm. Design 1 (1995) 255
5. Dal Paiz V., and Giovannoni M.P. Eur. J. Med. Chem. 35 (2000) 463
6. Campillo N., and Paez J.A. Expert Opin. Ther. Patents 12 (2002) 53
7. Burnouf C., Devillers I., and Pruniaux M.-P. Frontiers Med. Chem. Online 1 (2004) 293
8. Norman P. Expert Opin. Ther. Patents 12 (2002) 93
9. Montana J.G., and Dyke H.J. Expert Opin. Invest. Drugs 11 (2002) 1
10. Barnette M.S., Christensen S.B., Essayan D.M., Grous M., Prabhakar U., Rush J.A., Kagey-Sobotka A., and Torphy T.J. J. Pharmacol. Exp. Ther. 284 (1998) 420
11. Griswold D.E., Webb E.F., Badger A.M., Gorycki P.D., Levandoski P.A., Barnette M.A., Grous M., Christensen S., and Torphy T.J. J. Pharmacol. Exp. Ther. 287 (1998) 705
12. Hatzelmann A., and Schudt C. J. Pharmacol. Exp. Ther. 297 (2001) 267
13. Bundschuh D.S., Eltze M., Barsig J., Wollin L., Hatzelmann A., and Beume R. J. Pharmacol. Exp. Ther. 297 (2001) 280
14. Lipworth B.J. Lancet 365 (2005) 167
15. IUPAC name for rhodanine is 2-thioxothiazolidin-4-one.
16. Boschelli D.H., Connor D.T., Kuipers P.J., and Wright C.D. Bioorg. Med. Chem. Lett. 2 (1992) 705
17. Grant E.B., Guiadeen D., Baum E.Z., Foleno B.D., Jin H., Montenegro D.A., Nelson E.A., Bush K., and Hlasta D.J. Bioorg. Med. Chem. Lett. 10 (2000) 2179
18. Whitesitt C.A., Simon R.L., Reel J.K., Sigmund S.K., Phillips M.L., Shadle J.K., Heinz L.J., Koppel G.A., Hunden D.C., Lifer S.L., Berry D., Ray J., Little S.P., Liu X., Marshall W.S., and Panetta J.A. Bioorg. Med. Chem. Lett. 6 (1996) 2157
19. Sing W.T., Lee C.L., Yeo S.L., Lim S.P., and Sim M.M. Bioorg. Med. Chem. Lett. 11 (2001) 91
20. Fujishima H., and Tsubota K. Br. J. Ophthalmol. 86 (2002) 860
21. Orchard M.G., Neuss J.C., Galley C.M.S., Carr A., Porter D.W., Smith P., Scopes D.I.C., Haydon D., Vousden K., Stubberfield C.R., Young K., and Page M. Bioorg. Med. Chem. Lett. 14 (2004) 3975
22. Cutshall N.S., O'Day C., and Prezhdo M. Bioorg. Med. Chem. Lett. 15 (2005) 3374
23. IUPAC name for pseudothiohydantoin is 2-thioxo-imidazolidin-4-one.
24. Zimmer H., Armbruster D.C., and Trauth L.J. J. Heterocyclic Chem. 2 (1965) 171
25. Phillips M.L., Berry D.M., and Panetta J.A. J. Org. Chem. 57 (1992) 4047
26. Brown F.C., Bradsher C.K., McCallum S.G., and Potter M. J. Org. Chem. 15 (1950) 174
27. Gibson L.C.D., Hastings S.F., McPhee I., Clayton R.A., Darroch C.E., Mackenzie A., Mackenzie F.L., Nagasawa M., Stevens P.A., and Mackenzie S.J. Eur. J. Pharmacol. 538 (2006) 39
28. Marivet M.C., Bourguignon J.-J., Lugnier C., Mann A., Stoclet J.-C., and Wermuth C.-G. J. Med. Chem. 32 (1989) 1450
29. Brown F.C., Bradsher C.K., and Bond S.M. Ind. Eng. Chem. 45 (1953) 1030
30. Scott A.W., and Robbins T.E. Ind. Eng. Chem., Anal. Ed. 14 (1942) 206
31. Grundon M.F., and Perry H.J.H. J. Chem. Soc. (1954) 3531
32. Campaigne E., and Kreighbaum W.E. J. Org. Chem. 26 (1961) 1326
33. Wong E. J. Org. Chem. 28 (1963) 2336
34. Stafford J.A., Feldman P.L., Marron B.E., Schoenen F.J., Valvano N.L., Unwalla R.J., Domanico P.L., Brawley E.S., Leesnitzer M.A., Rose D.A., and Dougherty R.W. Bioorg. Med. Chem. Lett. 4 (1994) 1855
35. The dipole orientation in 2a and 2s was investigated by generating the global minimum energy conformations of these compounds within the Insight-II molecular modeling package (Accelrys, Cambridge, UK).
36. Huai Q., Wang H., Sun Y., Kim H.-W., Lui Y., and Ke H. Structure 11 (2003) 865
37. Card G.L., England B.P., Suzuki Y., Fong D., Powell B., Lee B., Luu C., Tabrizizad M., Gillette S., Ibrahim P.N., Artis D.R., Bollag G., Milburn M.V., Kim S.-H., Schlessinger J., and Zhang K.Y.J. Structure 12 (2004) 2233
38. Xu R.X., Rocque W.J., Lambert M.H., Vanderwall D.E., Luther M.A., and Nolte R.T. J. Mol. Biol. 337 (2004) 355
39. Villemin D., and Alloum A.B. Phosphorus, Sulfur Silicon Relat. Elem. 79 (1993) 33
40. Andreasch R., and Zipser A. Monatsh. Chem. 25 (1904) 159
41. Yang D.-H., Chen Z.-C., Chen S.-Y., and Zheng Q.-G. J. Chem. Res., Synop. 6 (2003) 330