Novel tricyclic Δ2-isoxazoline and 3-oxo-2-methyl-isoxazolidine derivatives: Synthesis and binding affinity at neuronal nicotinic acetylcholine receptor subtypes

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 12, 2010, Pages 4498-4508

  Dallanoce, Clelia ^a   Frigerio, Fabio ^a   Martelli, Giuliana ^a   Grazioso, Giovanni ^a   Matera, Carlo ^a   Pomè, Diego Yuri ^a   Pucci, Luca ^a   Clementi, Francesco ^a   Gotti, Cecilia ^a   Amici, Marco De ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

2 Isoxazoline and 3 oxo isoxazolidine derivatives; Binding affinity; Cytisine and ferruginine analogues; Molecular modeling; Neuronal nicotinic acetylcholine receptors

Indexed keywords

3 BROMO 5 OXA 4,10 DIAZATRICYCLO[6.3.1.02,6]DODEC 3 ENE; 3 BROMO 5 OXA 4,11 DIAZATRICYCLO[6.2.1.02,6]UNDEC 3 ENE; 3 METHOXY 5 OXA 4,11 DIAZATRICYCLO[6.2.1.02,6]UNDEC 3 ENE; 5 BROMO 3 OXA 4,11 DIAZATRICYCLO[6.2.1.02,6]UNDEC 4 ENE; 5 METHOXY 3 OXA 4,10 DIAZATRICYCLO[6.3.1.02,6]DODEC 4 ENE (5A) AND 3 METHOXY 5 OXA 4,10 DIAZATRICYCLO[6.3.1.02,6] DODEC 3 ENE; 5 METHOXY 3 OXA 4,11 DIAZATRICYCLO[6.2.1.02,6]UNDEC 4 ENE; ALPHA BUNGAROTOXIN; ISOXAZOLIDINE DERIVATIVE; ISOXAZOLINE DERIVATIVE; NICOTINIC RECEPTOR; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG; 3-BROMO-5-OXA-4,10-DIAZATRICYCLO(6.3.1.0(2,6))DODEC-3-ENE; 5-BROMO-3-OXA-4,11-DIAZATRICYCLO(6.2.1.0(2,6))UNDEC-4-ENE; ALKALOID; AZOCINE DERIVATIVE; BUNGAROTOXIN RECEPTOR; CHRNA7 PROTEIN, RAT; CYTISINE; FERRUGININE; FUSED HETEROCYCLIC RINGS; ISOXAZOLE DERIVATIVE; LIGAND; NICOTINIC RECEPTOR ALPHA4BETA2; PROTEIN BINDING; QUINOLIZINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; COLUMN CHROMATOGRAPHY; CYCLOADDITION; DRUG BINDING; DRUG SYNTHESIS; MEMBRANE BINDING; MOLECULAR DOCKING; STRUCTURAL HOMOLOGY; THIN LAYER CHROMATOGRAPHY; ANIMAL; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NERVE CELL; RAT; SYNTHESIS;

ALKALOIDS; ANIMALS; AZOCINES; BICYCLO COMPOUNDS, HETEROCYCLIC; BINDING SITES; HETEROCYCLIC COMPOUNDS, 3-RING; ISOXAZOLES; LIGANDS; MODELS, MOLECULAR; NEURONS; PROTEIN BINDING; QUINOLIZINES; RATS; RECEPTORS, NICOTINIC; ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR;

EID: 77953323415     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.04.065     Document Type: Article

References (49)

1. Dale H.H. Pharmacol. Rev. 6 (1954) 7
2. Schmitt J.D. Curr. Med. Chem. 7 (2000) 749
3. Dajas-Bailador F., and Wonnacott S. Trends Pharmacol. Sci. 25 (2004) 317
4. Exley R., and Cragg S.J. Br. J. Pharmacol. 153 (2008) S283
5. Jensen A.A., Frølund B., Liljefors T., and Krogsgaard-Larsen P. J. Med. Chem. 48 (2005) 4705
6. Romanelli M.N., Gratteri P., Guandalini L., Martini E., Bonaccini C., and Gualtieri F. ChemMedChem 2 (2007) 746
7. Kalamida D., Poulas K., Avramopoulou V., Fostieri E., Lagoumintzis G., Lazaridis K., Sideri A., Zouridakis M., and Tzartos S.J. FEBS J. 274 (2007) 3799
8. Gotti C., and Clementi F. Prog. Neurobiol. 74 (2004) 363
9. Gotti C., Zoli M., and Clementi F. Trends Pharmacol. Sci. 27 (2006) 482
10. Cincotta S.L., Yorek M.S., Moschak T.M., Lewis S.R., and Rodefer J.S. Curr. Opin. Invest. Drugs 9 (2008) 47
11. Daly D.W. Cell. Mol. Neurobiol. 25 (2005) 513 and references cited therein
12. Partheil A. Ber. 23 (1890) 3201
13. Ing H.R. J. Chem. Soc. (1931) 2195
14. Bick R.C., Gillard J.W., and Leow H.M. Austr. J. Chem. 32 (1979) 2537
15. Gohlke H., Gündish D., Schwartz S., Seitz G., Tilotta M.C., and Wegge T. J. Med. Chem. 45 (2002) 1064
16. Gohlke H., Schwartz S., Gündish D., Tilotta M.C., Weber A., Wegge T., and Seitz G. J. Med. Chem. 46 (2003) 2031 and references cited therein
17. Cassels B.K., Bermúdez I., Dajas F., Abin-Carriquiri J.A., and Wonnacott S. Drug Disc. Today 10 (2005) 1657
18. Meyer E.L., Xiao Y., and Kellar K.J. Mol. Pharmacol. 60 (2001) 568
19. Eaton J.B., Peng J.H., Schroeder K.M., George A.A., Fryer J.D., Krishnan C., Buhlman L., Kuo Y.P., Steinlein O., and Lukas R.J. Mol. Pharmacol. 64 (2003) 1283
20. Slater Y.E., Houlihan L.M., Maskell P.D., Exley R., Bermúdez I., Lukas R.J., Valdivia A.C., and Cassels B.K. Neuropharmacology 44 (2003) 503
21. Imming P., Klaperski P., Stubbs M.T., Seitz G., and Gündisch D. Eur. J. Med. Chem. 36 (2001) 375
22. Houlihan L.M., Slater Y.E., Guerra D.L., Peng J.H., Kuo Y.P., Lukas R.J., Cassels B.K., and Bermúdez I. J. Neurochem. 78 (2001) 1029
23. Kozikowski A.P., Chellappan S.K., Xiao Y., Bajjuri K.M., Yuan H., Kellar K.J., and Petukhov P.A. ChemMedChem 2 (2007) 1157
24. Carbonnelle E., Sparatore F., Canu-Boido C., Salvagno C., Baldani-Guerra B., Terstappen G., Zwart R., Vijverberg H., Clementi F., and Gotti C. Eur. J. Pharmacol. 471 (2003) 85
25. Tasso B., Canu-Boido C., Terranova E., Gotti C., Riganti L., Clementi F., Artali R., Bombieri G., Meneghetti F., and Sparatore F. J. Med. Chem. 52 (2009) 4345
26. Dallanoce C., Bazza P., Grazioso G., De Amici M., Gotti C., Riganti L., Clementi F., and De Micheli C. Eur. J. Org. Chem. (2006) 3746 and references cited therein
27. De Micheli, C.; De Amici, M.; Dallanoce, C.; Clementi, F.; Gotti, C. PCT Int. Appl. WO 2008000469, 2008.
28. Rizzi L., Dallanoce C., Matera C., Magrone P., Pucci L., Gotti C., Clementi F., and De Amici M. Bioorg. Med. Chem. Lett. 18 (2008) 4651
29. Grazioso G., Pomè D.Y., Matera C., Frigerio F., Pucci L., Gotti C., Dallanoce C., and De Amici M. Bioorg. Med. Chem. Lett. 19 (2009) 6353
30. Vyas D.M., Chiang Y., and Doyle T.W. Tetrahedron Lett. 25 (1984) 487
31. Esch P.M., Hiemstra H., de Boer R.F., and Speckamp W.N. Tetrahedron 48 (1992) 4659
32. Udding J.H., Papin N., Hiemstra H., and Speckamp W.N. Tetrahedron 50 (1994) 8853
33. In: Eliel E.L., and Wilen S.H. (Eds). Stereochemistry of Organic Compounds (1994), John Wiley & Sons, New York 665-834 Chapter 11
34. In Basic Terminology of Stereochemistry (IUPAC Recommendations 1996), available at the site http://www.chem.qmul.ac.uk/iupac/stereo/DE.html.
35. gaussian03, Revision B.04, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N. J.; Burant, C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, S.; Clifford, J.; Cioslowski, B. B.; Stefanov, G.; Liu, A.; Liashenko, P.; Piskorz, I.; Komaromi, A. G.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian: Wallingford CT, 2004.
36. Lin R., Castells J., and Rapoport H. J. Org. Chem. 63 (1998) 4069
37. Aggarwal V.K., Astle C.J., and Rogers-Evans M. Org. Lett. 6 (2004) 1469
38. Berdini V., Cesta M.C., Curti R., D'Anniballe G., Di Bello N., Nano G., Nicolini L., Topai A., and Allegretti M. Tetrahedron 58 (2002) 5569
39. Napier, S. E.; Bingham, M. J.; Dunbar, N. A. PCT Int. Appl. WO 2007/063071, 2007.
40. Baldwin J.E., Ng S.C., and Pratt A.J. Tetrahedron Lett. 28 (1987) 4319
41. Hanamoto T., Egashira M., Ishizuka K., Furuno H., and Inanaga J. Tetrahedron 62 (2006) 6332
42. Munson P.J., and Rodbard D. Anal. Biochem. 107 (1980) 220
43. Sgrignani J., Bonaccini C., Grazioso G., Chioccioli M., Cavalli A., and Gratteri P. J. Comp. Chem. 30 (2009) 2443
44. Pedersen H., Sinning S., Bülow A., Wiborg O., Falborg L., and Bols M. Org. Biomol. Chem. 2 (2004) 2861
45. Gerzanich V., Peng X., Wang F., Wells G., Anand R., Fletcher S., and Lindstrom J. Mol. Pharmacol. 48 (1995) 774
46. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
47. gold v. 3.2, Cambridge Crystallographic Data Centre: Cambridge, UK.
48. DeLano, W. L. The PyMOL Molecular Graphics System, 2002, DeLano Scientific: Palo Alto, CA, USA. http://www.pymol.org.
49. Zhang N., Tomizawa M., and Casida J. Bioorg. Med. Chem. Lett. 13 (2003) 525