Identification and SAR of potent and selective non-peptide obeline somatostatin sst1 receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 14, 2007, Pages 3983-3987

  Troxler, Thomas ^a   Hoyer, Daniel ^a   Langenegger, Daniel ^a   Neumann, Peter ^a   Pfäffli, Paul ^a   Schoeffter, Philippe ^a   Sorg, Dieter ^a   Swoboda, Robert ^a   Hurth, Konstanze ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Octahydrobenzo g quinolines (obelines); Somatostatin sst1 receptor antagonists

Indexed keywords

LIGAND; OBELINE DERIVATIVE; QUINOLINE DERIVATIVE; RECEPTOR SUBTYPE; SOMATOSTATIN RECEPTOR; SOMATOSTATIN RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DERIVATIZATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; HUMANS; LUMINESCENT PROTEINS; RATS; RECEPTORS, SOMATOSTATIN; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34250345551     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.04.086     Document Type: Article

References (39)

1. Brazeau P., Vale W., Burgus R., Ling N., Butcher M., Rivier J., and Guillemin R. Science 179 (1973) 77
2. Gerich J.E., Lovinger R., and Grodsky G.M. Endocrinology 96 (1975) 749
3. Johansson C., Wisen O., Efendic S., and Uvnas-Wallensten K. Digestion 22 (1981) 126
4. Lamberts S.W., Krenning E.P., and Reubi J.C. Endocr. Rev. 12 (1991) 450
5. Schettini G. Pharmacol. Res. 23 (1991) 203
6. Havlicek V., Rezek M., and Friesen H. Biochem. Behav. 4 (1976) 455
7. Chesselet M.F., and Reisine T.D. J. Neurosci. 3 (1983) 232
8. Gothert M. Nature 288 (1980) 86
9. Gillies G. Trends Parmacol. Sci. 18 (1997) 87
10. Dournaud P., Jazat-Poindessous F., Slama A., Lamour Y., and Epelbaum J. Eur. J. Neurosci. 8 (1996) 476
11. Patel Y.C. Front. Neuroendocrinol. 20 (1999) 157
12. Hoyer D., Bell G.I., Berelowitz M., Epelbaum J., Feniuk W., Humphrey P.P.A., O'Carroll A.-M., Patel Y.C., and Schonbrunn A. Trends Pharmacol. Sci. 16 (1995) 86
13. Bell G.I., and Reisine T. Trends Neurosci. 16 (1993) 34
14. Lloyd K.C., Amirmoazzami S., Friedik F., Chew P., and Walsh J.H. Am. J. Physiol. 272 (1997) G1481
15. Rossowski W.J., and Coy D.H. Biochem. Biophys. Res. Commun. 205 (1994) 341
16. Lanneau C., Bluet-Pajot M.T., Zizzari P., Csaba Z., Dournaud P., Helboe L., Hoyer D., Pellegrini E., Tannenbaum G.S., Epelbaum J., and Gardette R. Endocrinology 14 (2000) 967
17. DalMonte M., Petrucci C., Cervia D., Vasilaki A., Drouselle D., Epelbaum J., Richter D., Hoyer D., and Bagnoli P. Neuropharmacology 45 (2003) 1080
18. Vasilaki A., Papasava D., Kocharyan A., Schulz S., Hoyer D., Meyerhof D., and Thermos K. Neuropharmacology 47 (2004) 612
19. Thermos K., Bagnoli P., Epelbaum J., and Hoyer D. Pharmacol. Ther. 110 (2006) 455
20. Hannon J.P., Nunn C., Stolz B., Bruns C., Weckbecker G., Lewis I., Troxler T., Hurth K., and Hoyer D. J. Mol. Neurosci. 18 (2002) 15
21. Hirschmann R., Nicolaou K.C., Pietranico S., Leahy E.M., Salvino J., Arison B., Cichy M.A., Spoors P.G., and Shakespeare W.C. J. Am. Chem. Soc. 115 (1993) 12550
22. Papageorgiou C., Haltiner R., Bruns C., and Petcher T.J. Bioorg. Med. Chem. Lett. 2 (1992) 135
23. Damour D., Barreau M., Blanchard J.-C., Burgevin M.-C., Doble A., Herman F., Pantel G., James-Surcouf E., and Vuilhorgne M. Bioorg. Med. Chem. Lett. 6 (1996) 1667
24. Papageorgiou C., and Borer X. Bioorg. Med. Chem. Lett. 6 (1996) 267
25. Liu S., Tang C., Ho B., Ankersen M., Stidsen C.E., and Crider A.M. J. Med. Chem. 41 (1998) 4693
26. Rohrer S.P., Birzin E.T., Mosley R.T., Berk S.C., Hutchins S.M., Shen D.-M., Xiong Y., Hayes E.C., Parmar R.M., Foor F., Mitra S.W., Degrado S.J., Shu M., Klopp J.M., Cai S.-J., Blake A., Chan W.W.S., Pasternak A., Yang L., Patchett A.A., Smith R.G., Chapman K.T., and Schaeffer J.M. Science 282 (1998) 737
27. Berk S.C., Rohrer S.P., Degrado S.J., Birzin E.T., Mosley R.T., Hutchins S.M., Pasternak A., Schaeffer J.M., Underwood D.J., and Chapman K.T. J. Comb. Chem. 1 (1999) 388
28. Yang L., Guo L., Pasternak A., Mosley R., Rohrer S., Birzin E., Foor F., Cheng K., Schaeffer J., and Patchett A.A. J. Med. Chem. 41 (1998) 2175
29. Yang L., Berk S.C., Rohrer S.P., Mosley R.T., Guo L., Underwood D.J., Arison B.H., Birzin E.T., Hayes E.C., Mitra S.W., Parmar R.M., Cheng K., Wu T.J., Butler B.S., Foor F., Pasternak A., Pan Y., Silva M., Freidinger R.M., Smith R.G., Chapman K., Schaeffer J.M., and Patchett A.A. Proc. Natl. Acad. Sci. USA 95 (1998) 10836
30. Nunn C., Rueping M., Langenegger D., Schuepbach E., Kimmerlin T., Micuch P., Hurth K., Seebach D., and Hoyer D. Naunyn-Schmiedeberg's Arch. Pharmacol. 367 (2003) 95
31. Hay B.A., Cole B.M., DiCapua F.M., Kirk G.W., Murray M.C., Nardone R.A., Pelletier D.J., Ricketts A.P., Robertson A.S., and Siegel T.W. Bioorg. Med. Chem. Lett. 11 (2001) 2731
32. Moinet C., Contour-Galcera M.-O., Poitout L., Morgan B., Gordon T., Roubert P., and Thurieau C. Bioorg. Med. Chem. Lett. 11 (2001) 991
33. Poitout L., Roubert P., Contour-Galcera M.-O., Moinet C., Lannoy J., Pommier J., Plas P., Bigg D., and Thurieau C. J. Med. Chem. 44 (2001) 2990
34. Hurth K., Floersheim P., Hoyer D., Langenegger D., Neumann P., Pfäffli P., Sorg D., Swoboda R., and Troxler T. Bioorg. Med. Chem. Lett. 17 (2007) 3988-3991
35. Pfaeffli, P.; Neumann, P.; Swoboda, R.; Stütz, P. PCT Int. Appl. WO 9854183, 1998; Chem. Abstr. 1998, 130, 25220.
36. Hoyer D., Perez J., Schoeffter P., Langenegger D., Schüpbach E., Kaupmann K., Lübbert H., Bruns C., and Reubi J.C. Eur. J. Pharmacol. 289 (1995) 151
37. Nordmann R., and Petcher T.J. J. Med. Chem. 28 (1985) 367
38. All compounds listed in Tables 1-3 were prepared according to procedures given as Supporting information.
39. d of 8.60 for the native rat brain cortex sst1 receptor. The data in Tables 1-3 apply to the free base