Synthesis and biological evaluation of novel fluoro and iodo quinoline carboxamides as potential ligands of NK-3 receptors for in vivo imaging studies

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 16, 2004, Pages 4533-4541

  Bennacef, Idriss ^a,b   Tymciu, Sylvie ^a   Dhilly, Martine ^a   Lasne, Marie Claire ^b   Debruyne, Danielle ^a   Perrio, Cécile ^a,b   Barré, Louisa ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

Fluorine; Iodine; Ligand; NK 3 receptor; Quinoline carboxamide

Indexed keywords

AMIDE; N (1 PHENYLPROPYL) 6 FLUORO 3 HYDROXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 6 FLUORO 3 METHOXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 6 IODO 3 HYDROXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 6 IODO 3 METHOXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 7 FLUORO 3 HYDROXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 7 FLUORO 3 METHOXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 7 IODO 3 HYDROXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 7 IODO 3 METHOXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 8 FLUORO 3 HYDROXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 8 FLUORO 3 METHOXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 8 IODO 3 HYDROXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (1 PHENYLPROPYL) 8 IODO 3 METHOXY 2 PHENYLQUINOLINE 4 CARBOXAMIDE; N (ALPHA ETHYLBENZYL) 3 METHYL 2 PHENYL 4 QUINOLINECARBOXAMIDE; NEUROKININ 3 RECEPTOR; NEUROKININ A; NEUROKININ B; QUINOLINE DERIVATIVE; SENKTIDE; SUBSTANCE P; TALNETANT; UNCLASSIFIED DRUG; FLUORINE; IODINE; LIGAND;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; FLUORINATION; IMAGING SYSTEM; IN VIVO STUDY; IODINATION; NEUROIMAGING; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RECEPTOR BINDING; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; CHEMISTRY; METABOLISM; SYNTHESIS;

FLUORINE; IODINE; LIGANDS; POSITRON-EMISSION TOMOGRAPHY; QUINOLINES; RECEPTORS, NEUROKININ-3; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 3242809004     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.05.020     Document Type: Article

References (29)

1. Maggio J.E. Annu. Rev. Neurosci. 11:1988;13-28
2. Regoli D., Boudon A., Fauchere J.L. Pharmacol. Rev. 46:1994;551-599
3. Gao Z., Peet N.P. Curr. Med. Chem. 6:1999;375-388
4. Maggi C.A. Gen. Pharmacol. 26:1995;911-944
5. Gerard N.P., Eddy R.L.J., Shows T.B., Gerard C. J. Biol. Chem. 265:1990;20455-20462
6. Buell G., Schulz M.F., Arkinstall S.J., Maury K., Missotten M., Adami N., Talabot F., Kawashima E. FEBS Lett. 299:1992;90-95
7. Huang R.R.C., Cheung A.H., Mazina K.E., Strader C.D., Fong T.M. Biochem. Biophys. Res. Commun. 184:1992;962-966
8. Langlois X., Wintmolders C., Te Riele P., Leyse J.E., Jurzack M. Neuropharm. 40:2001;242-253
9. Langlois X., Te Riele P., Wintmolders C., Leyse J.E., Jurzack M. J. Pharmacol. Exp. Ther. 299:2001;712-717
10. Saffroy M., Torrens Y., Glowinski J., Beaujouan J.-C. Neuroscience. 116:2003;761-773
11. Mileusnic D., Lee J.M., Magnuson D.J., Hejna M.J., Krause J.E., Lorens J.B., Lorens S.A. Neuroscience. 89:1999;1269-1290
12. Tooney P.A., Au G.G., Chahl L.A. Neurosci. Lett. 283:2000;185-188
13. Giardina G.A.M., Grugni M., Raveglia L.F. Exp. Opin. Ther. Patents. 10:2000;939-960
14. Alonso R., Fournier M., Carayon P., Petitpretre G., Le Fur G., Soubrié P. Eur. J. Neurosci. 8:1996;801-808
15. Jung M., Michaud J.C., Steinberg R., Barnouin M.C., Hayar A., Mons G., Souilhac J., Emonds-Alt X., Soubrié P., Le Fur G. Neuroscience. 74:1996;403-414
16. Marco N., Thirion A., Mons G., Bougault I., Le Fur G., Soubrié P., Steinberg R. Neuropeptides. 32:1998;481-488
17. Emonds-Alt X., Bichon D., Ducoux J.P., Heaulme M., Miloux B., Poncelet M., Proietto V., van Broeck D., Vilain P., Neliat G., Soubrié P. Life Sci. 56:1995;27-32
18. Farina, C.; Giardina, G. A. M.; Grugni, M.; Raveglia, L. F. PCT Int. App. WO 9532948, 1995. Chem. Abstr. 1995, 124, 232269b
19. Giardina G.A.M., Raveglia L.F., Grugny M., Sarau H.M., Farina C., Medhurtst A.D., Graziani D., Schmidt D.B., Rigolio R., Luttmann M., Cavagnera S., Foley J.J., Vecchietti V., Hay D.W.P. J. Med. Chem. 42:1999;1053-1065
20. Sarau H.M., Griswold D.E., Potts W., Foley J.J., Schmidt D.B., Webb E.F., Martin L.D., Brawner M.E., Elshourbagy N.A., Medhurst A.D., Giardina G.A.M., Hay D.W.P. J. Pharmacol. Exp. Ther. 281:1997;1303-1311
21. Giardina G.A.M., Raveglia L.F., Grugny M., Sarau H.M., Farina C., Medhurst A.D., Graziana D., Schmidt D.B., Rigolio R., Luttmann M., Cavagnera S., Foley J.J., Vecchietti V., Hay D.W.P. J. Med. Chem. 40:1997;1797-1807
22. Cheng C.-C., Yan S.-J. Org. React. 28:1982;37
23. Sadler P.W. J. Org. Chem. 21:1956;169-170
24. McKittrick B., Failli A., Steffan R.J., Soll R.M., Hugues P., Schmid J., Asselin A.A., Shaw C.C., Noureldin R., Gavin G. J. Heterocycl. Chem. 27:1990;2151-2163
25. Sarau H.M., Griswold D.E., Bush B., Potts W., Sandhu P., Lundberg D., Foley J.J., Schmidt D.B., Webb E.F., Martin L.D., Legos J.J., Whitmore R.G., Barone F.C., Medhurst A.D., Luttmann M.A., Giardina G.A., Hay D.W. J. Pharmacol. Exp. Ther. 295:2000;373-381
26. Guard S., Watson S.P., Maggio J.E., Too H.P., Watling K. Br. J. Pharmacol. 99:1990;767-773
27. Suman-Chauban N., Grimson P., Guard S., Madden Z., Chung F.-Z., Watling K.J., Pinnock R.D., Woodruff G.N. Eur. J. Pharmacol. 269:1994;65-72
28. Sagot M.A., Wijkhuisen A., Creminon C., Tymciu S., Frobert Y., Turbica I., Grassi J., Couraud J.Y., Boquet D. Mol. Pharmacol. 37:2000;423-433
29. Cheng Y.C., Prusoff W.H. Biochem. Pharmacol. 22:1973;3099-3108