Design, synthesis, and biological evaluation of indole derivatives as novel nociceptin/orphanin FQ (N/OFQ) receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 13, 2006, Pages 3569-3573

  Sugimoto, Yuichi ^a   Shimizu, Atsushi ^a   Kato, Tetsuya ^a   Satoh, Atsushi ^a   Ozaki, Satoshi ^a   Ohta, Hisashi ^a   Okamoto, Osamu ^a  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Antagonist; Indole; Nociceptin; ORL 1 receptor; Orphanin FQ

Indexed keywords

2 (1,2,4 OXADIAZOL 5 YL) 1H INDOLE; CARBOXYLIC ACID DERIVATIVE; ETHYL 1H INDOLE 2 CARBOXYLIC ACID; INDOLE DERIVATIVE; NOCICEPTIN RECEPTOR; NOCICEPTIN RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; NONHUMAN; SCANNING ELECTRON MICROSCOPY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; CELL MEMBRANE; CHO CELLS; CRICETINAE; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; HUMANS; INDOLES; MOLECULAR STRUCTURE; RECEPTORS, OPIOID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646849246     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.03.086     Document Type: Article

References (47)

1. Barlocco D., Cignarella G., Giardina G.A.M., and Toma L. Eur. J. Med. Chem. 35 (2000) 275
2. Zaveri N. Life Sci. 73 (2003) 663
3. Bignan G.C., Connolly P.J., and Middleton S.A. Expert Opin. Ther. Patents 15 (2005) 357
4. Mollereau C., Parmentier M., Mailleux P., Butour J., Moisand C., Chalon P., Caput D., Vassart G., and Meunier J.-C. FEBS Lett. 341 (1994) 33
5. Fukuda K., Kato S., Mori K., Nishi M., Takeshima H., Iwabe N., Miyata T., Houtani T., and Sugimoto T. FEBS Lett. 343 (1994) 42
6. Chen Y., Fan Y., Liu J., Mestek A., Tian M., Kozak C.A., and Yu L. FEBS Lett. 347 (1994) 279
7. Meunier J.-C., Mollereau C., Toll L., Suaudeau C., Moisand C., Alvinerie P., Butour J.-L., Guillemot J.-C., Ferrara P., Monsarrat B., Mazargil H., Vassart G., Parmentier M., and Costentin J. Nature 377 (1995) 532
8. Reinscheid R.K., Nothacher H.-P., Bourson A., Ardati A., Henningsen R.A., Bunzow J.R., Grady D.K., Langen H., Monsma Jr. F.J., and Civelli O. Science (1995) 270
9. Meunier J.-C. Eur. J. Pharmacol. 340 (1997) 1
10. Bigoni R., Giuliani S., Calo' G., Rizzi A., Guerrini R., Salvadori S., Regoli D., and Maggi C.A. Naunyn Schmiedebergs Arch. Pharmacol. 359 (1999) 160
11. Mollereau C., and Mouledous L. Peptides 21 (2000) 907
12. Mogil J.S., Grisel J.E., Reinscheid R.K., Civelli O., Belknap J.K., and Grandy D.K. Neuroscience 75 (1996) 333
13. Calo' G., Guerrini R., Rozzo A., Salvadori S., and Regoli D. Br. J. Pharmacol. 129 (2000) 1261
14. Calo' G., Rizzi A., Bigoni R., Guerrini R., Salvadori S., and Regoli D. Clin. Exp. Pharmacol. Physiol. 29 (2002) 223
15. Ueda H., Yamaguchi T., Tokuyama S., Inoue M., Nishi M., and Takeshima H. Neurosci. Lett. 237 (1997) 136
16. Kawamoto H., Ozaki S., Itoh Y., Miyaji M., Arai S., Nakashima H., Kato T., Ohta H., and Iwasawa Y. J. Med. Chem. 42 (1999) 5061
17. Ito, F.; Noguchi, H.; Ohashi, Y.; Kondo, H.; Yamagishi, T. WO 99/36421, 1999.
18. Kyle, D.; Goehring, R. R.; Shao, B. WO 01/39775 A1, 2001.
19. Ito, F.; Noguchi, H.; Kondo, H. US 6172067 B1, 2001.
20. Ito, F.; Noguchi, H.; Ohashi, Y.; Shimokawa, H. EP 1122257 A1, 2001.
21. Ito, F. US 6340681 B1, 2002.
22. Zaveri N.T., Jiang F., Olsen C.M., Deschamps J.R., Parrish D., Polgar W., and Toll L. J. Med. Chem. 47 (2004) 2973
23. Bignan G.C., Battista K., Connolly P.J., Orsini M.J., Liu J., Middleton S.A., and Reitz A.B. Bioorg. Med. Chem. Lett. 15 (2005) 5022
24. Rover S., Adam G., Cesura A.M., Galley G., Jenck F., Monsma F.J., Wichmann J., and Dautzenberg F.M. J. Med. Chem. 43 (2000) 1329
25. Kolczweski S., Adam G., Cesura A.M., Jenck F., Hennig M., Oberhauser T., Poli S.M., Rossler F., Rover S., Wichmann J., and Dautzenberg F.M. J. Med. Chem. 46 (2003) 255
26. Thomsen C., and Hohlweg R. Br. J. Pharmacol. 131 (2000) 903
27. Ito, F.; Ohashi, Y. EP 0997464 A1, 2000.
28. Kawamoto, H.; Ozaki, S.; Ito, Y.; Iwasawa, Y. JP 2000169476, 2000.
29. Satoh, A.; Kato, T.; Iwasawa, Y.; Ooi, N. WO 01/96337, 2001.
30. Arai, T.; Nishikimi, Y.; Imamura, S.; Kamiyama, K.; Kobayashi, M. WO 02/26714 A1, 2002.
31. Cesura, A. M.; Hoffmann, T.; Rover, S.; Wichmann, J. WO 00/14067, 2000.
32. Barlocco, D.; Cignarella, G.; Giardina, G.; Grugni, M.; Ronzoni, S. WO 00/27815, 2000.
33. Tulshian, D.; Ho, G. D.; Silverman, L. S.; Matasi, J. J.; McLeod, R. L.; Hey, J. A.; Chapman, R. W.; Bercovici, A.; Cuss, F. M. WO 01/07050, 2001.
34. Zaratin P.F., Petrone G., Sbacchi M., Garnier M., Fossati C., Petrillo P., Ronzoni S., Giardina G.A.M., and Scheideler M. J. Pharmacol. Exp. Ther. 308 (2004) 454
35. Shinkai H., Ito T., Iida T., Kitao Y., Yamada H., and Uchida I. J. Med. Chem. 43 (2000) 4667
36. Patent literature WO 96/03400 A1 describes a series of 4-indole derivatives as having affinity for serotonin receptors.
37. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893
38. DeSimone R.W., Currie K.S., Mitchell S.A., Darrow J.W., and Pippin D.A. Comb. Chem. High Throughput Screening 7 (2004) 473
39. Henn L., Hickey D.M.B., Moody C.J., and Rees C.W. J. Chem. Soc. Perkin Trans. I (1984) 2189
40. Hickey D.M.B., Mackenzie R., Moody C.J., and Rees C.W. J. Chem. Soc. Perkin Trans. I (1987) 921
41. 2, Pd/C].
42. Phillip A.J., Uto Y., Wipf P., Reno M.J., and Williams D.R. Org. Lett. 2 (2000) 1165
43. 35S]GTPγS binding assay was conducted as described previously:. Ozaki S., Kawamoto H., Itoh Y., Miyaji M., Azuma T., Ichikawa D., Nambu H., Iguchi T., Iwasawa Y., and Ohta H. Eur. J. Pharmacol. 402 (2000) 45
44. Synthesized from 5-bromo-2-methyl-1,2,3,4-tetrahydroisoquinoline.
45. Synthesized from 2-(4-pyridyl)benzaldehyde.
46. Synthesized from 2-chloronicotinaldehyde.
47. Synthesized from 4-bromonicotinaldehyde.