Nitrogen-bridged substituted 8-arylquinolines as potent PDE IV inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 10, 2006, Pages 2608-2612

  Lacombe, Patrick ^a   Deschênes, Denis ^a   Dubé, Daniel ^a   Dubé, Laurence ^a   Gallant, Michel ^a   Macdonald, Dwight ^a   Mastracchio, Antony ^a   Perrier, Hélène ^a   Charleson, Stella ^a   Huang, Zheng ^a   Laliberté, France ^a   Liu, Susana ^a   Mancini, Joseph A ^a   Masson, Paul ^a   Salem, Myriam ^a   Styhler, Angela ^a   Girard, Yves ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

Asthma; c AMP; COPD; PDE4; TNF

Indexed keywords

4 [2 [3 (CYCLOPENTYLOXY) 4 METHOXYPHENYL] 2 PHENYLETHYL]PYRIDINE; BRIDGED COMPOUND; NITROGEN; OVALBUMIN; PHOSPHODIESTERASE IV INHIBITOR; QUINOLINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BRONCHOSPASM; CONSCIOUSNESS; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENCY; DRUG SYNTHESIS; GUINEA PIG; HUMAN; IN VIVO STUDY; NONHUMAN; PHARMACOLOGICAL PARAMETERS; RAT; SQUIRREL MONKEY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BIOLOGICAL AVAILABILITY; HALF-LIFE; NITROGEN; PHOSPHODIESTERASE INHIBITORS; QUINOLINES; RATS; SAIMIRI;

ANIMALIA; CAVIA; CAVIA PORCELLUS; SAIMIRI;

EID: 33645851018     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.02.043     Document Type: Article

References (16)

1. Yuasa K., Kanoh Y., Okumura K., and Omori K. Eur. J. Biochem. 268 (2001) 168
2. Soderling S.H., and Beavo J.A. Curr. Opin. Cell Biol. 12 (2000) 174
3. Claveau D., Chen S.L., O'Keefe S., Zaller D.M., Styhler A., Liu S., Huang Z., Nicholson D.W., and Mancini J.A. J. Pharmacol. Exp. Ther. 310 2 (2004) 752
4. Jones T.R., McAuliffe M., McFarlane C.S., Piechuta H., Macdonald D., and Rodger I.W. Can. J. Physiol. Pharmacol. 76 (1998) 210
5. Danahay H., and Broadley K.J. Clin. Exp. Allergy 28 4 (1998) 513
6. Burnouf C., Pruniaux M.-P., and Szilagyi C.M. Ann. Rep. Med. Chem. 33 (1998) 91
7. Hughes B., Howat D., Lisle H., Holbrook M., James T., Gozzard N., Blease K., Hughes P., Kingaby R., Warrellow G., Alexander R., Head J., Boyd E., Eaton M., Perry M., Wales M., Smith B., Owens R., Catterall C., Lumb S., Russell A., Allen R., Merriman M., Bloxham D., and Higgs G. Br. J. Pharmacol. 118 (1996) 1183
8. Perry M.J., O'Connell J., Walker C., Crabbe T., Baldock D., Russell A., Lumb S., Huang Z., Howat D., Allen R., Merriman M., Walls J., Daniel T., Hughes B., Laliberte F., Higgs G.A., and Owens R.J. Cell Biochem. Biophys. 29 (1998) 113
9. Christensen S.B., Guider A., Forster C.J., Gleason J.G., Bender P.E., Karpinski J.M., DeWolf Jr. W.E., Barnette M.S., Underwood D.C., Griswold D.E., Cieslinski L.B., Burman M., Bochnowicz S., Osborn R.R., Manning C.D., Grous M., Hillegas L.M., Bartus J.O., Ryan M.D., Eggleston D.S., Haltiwanger R.C., and Torphy T.J. J. Med. Chem. 41 (1998) 821
10. Xu R.X., Hassell A.M., Vanderwall D., Lambert M.H., Holmes W.D., Luther M.A., Rocque W.J., Milburn M.V., Zhao Y., Ke H., and Nolte R.T. Science 288 (2000) 1822
11. Macdonald D., Mastracchio A., Perrier H., Dubé D., Gallant M., Lacombe P., Desch ênes D., Roy B., Scheigetz J., Bateman K., Li C., Trimble L.A., Day S., Chauret N., Nicoll-Griffith D.A., Silva J.M., Huang Z., Lalibert é F., Liu S., Ethier D., Pon D., Muise E., Boulet L., Chan C.C., Styler A., Charleson S., Mancini J., Masson P., Claveau D., Nicholson D., Turner M., Young R.N., and Girard Y. Bioorg. Med. Chem. Lett. 15 (2005) 5241
12. Laliberté F., Han Y., Govindarajan A., Giroux A., Liu S., Bobechko B., Lario P., Bartlett A., Gorseth E., Gresser M., and Huang Z. Biochemistry 39 (2000) 6449
13. Brideau C., Van Staden C., Styhler A., Rodger I.W., and Chan C.-C. Br. J. Pharmacol. 126 (1999) 979
14. Ortiz J.L., Vallés J.M., Marti-Cabrera M., Cortijo J., and Morcillo E.J. Naunyn-Schmiedeberg's Arch. Pharmacol. 353 (1996) 200
15. Jones T.R., and Masson P. Prostaglandins 29 (1985) 799
16. Separation of the two enantiomers was performed by chiral HPLC (Chiralpak AD 5 × 50 cm, 20 μ, 60 ml/min, 40% hexanes/60% ethanol, rt = 55 and 79 min.).