Modulation on C- and N-terminal moieties of a series of potent and selective linear tachykinin NK2 receptor antagonists

ChemMedChem

Volumn 5, Issue 1, 2010, Pages 65-78

  Gensini, Martina ^a   Altamura, Maria ^a   Dimoulas, Tula ^a   Fedi, Valentina ^a   Giannotti, Danilo ^a   Giuliani, Sandro ^a   Guidi, Antonio ^a   Harmat, Nicholas J S ^a   Meini, Stefania ^a   Nannicini, Rossano ^a   Pasqui, Franco ^a   Tramontana, Manuela ^a   Triolo, Antonio ^a   Maggi, Carlo Alberto ^a  

^a Menarini Ricerche SpA   (Italy)

Author keywords

Drug discovery; NK2 receptors; Structure activity relationships; Tachykinin

Indexed keywords

5 METHYLNAPHTHALENE 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE; 6 BROMONAPHTHALENE 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE TRIFLUOROACETATE; 6 METHYLBENZO[B]FURAN 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE; 6 METHYLBENZO[B]THIOPHEN 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE; 6 METHYLBENZO[B]THIOPHEN 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE TRIFLUOROACETATE; 6 METHYLNAPHTHALENE 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE TRIFLUOROACETATE; 7 METHYLBENZO[B]FURAN 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE; BENZO[B]FURAN 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE; NAPHTHALENE 2 CARBOXYLIC ACID [1 [2 PHENYL [[1 (TETRAHYDROPYRAN 4 YLMETHYL)PIPERIDIN 4 YLMETHYL]CARBAMOYL]ETHYLCARBAMOYL]CYCLOPENTYL]AMIDE; TACHYKININ RECEPTOR AGONIST; TACHYKININ RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG INHIBITION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; DIPEPTIDES; DRUG DESIGN; GUINEA PIGS; HUMANS; RECEPTORS, NEUROKININ-2; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 74849127704     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200900389     Document Type: Article

References (34)

1. a) C. A. Maggi, R. Patacchini, P. Rovero, A. Giachetti, J. Auton. Pharmacol. 1993, 13, 23-93;
2. b) S. H. Buck, the Tachykinin Receptors, Humana, Totowa, 1995.
3. a) Y. Shimizu, H. Matsuyama, T. Shiina T. Takewaki, J. B. Furness, Cell. Mol. Life Sci. 2008, 65, 295-311;
4. b) S. Evangelista, R. Patacchini, C. A. Maggi, Curr. Med Chem. Anti-Inflammatory Anti-Allergy Agents 2003, 2, 157-174.
5. a) A. Lecci, A. Capriati, M. Altamura, C. A. Maggi, Auton. Neurosci. 2006, 126-127, 232-249;
6. b) A. Lecci, M. Altamura, A. Capriati, C. A. Maggi, Riv. Eur. Sci. Med. Farmacol. Sci. 2008, 12, 69-80.
7. a) V. Fedi, M. Altamura, R. M. Catalioto, D. Giannotti, A. Giolitti, S. Giuliani, A. Guidi, N. J. S. Harmat, A. Lecci, S. Meini, R. Nannicini, F. Pasqui, M. Tramontana, A. Triolo, C. A. Maggi, J. Med. Chem. 2007, 50, 4793-4807;
8. b) C. Cialdai, M. Tramontana, R. Patacchini, A. Lecci, C. Catalani, R. M. Catalioto, S. Meini, C. Valenti, M. Altamura, S. Giuliani, C. A. Maggi, Eur. J. Pharmacol. 2006, 549, 140-148;
9. S. Giuliani, M. Altamura, C. A. Maggi, Drugs Future 2008, 33, 111-115;
10. S. Meini, F. Bellucci, C. Catalani, P. Cucchi, A. Giolitti, P. Santicioli, S. Giuliani, J. Pharm. Exp. Ther. 2009, 329, 486-495.
11. S. Meini, F. Bellucci, C. Catalani, P. Cucchi, R. Patacchini, L. Rotondaro, M. Altamura, S. Giuliani, A. Giolitti, C. A. Maggi, Eur. J. Pharmacol. 2004, 488, 61-69.
12. M. Altamura, M. Dapporto, V. Fedi, A. Giolitti, A. Guerri, A. Guidi, C. A. Maggi, P. Paoli, P. Rossi, Acta Crystallogr. Sect. B 2006, 62, 889-896.
13. S. Meini, F. Bellucci, C. Catalani, P. Cucchi, A. Giolitti, P. Santicioli, S. Giuliani, J. Pharmacol. Exp. Ther. 2009, 329, 486-495.
14. For the replacement of a tetrahydropyranyl moiety with a bicyclic system see: M. Altamura, A. Guidi, F. Pasqui, M. Tramontana, K. Worm-Leonhard, Lett. Drug Des. Discovery 2007, 4, 520-523.
15. For modifications with biphenyl and heterobiphenyl groups see: a) M. Porcelloni, P. D'Andrea, C. Rossi, A. Sisto, A. Ettorre, A. Madami, M. Altamura, S. Giuliani, S. Meini, D. Fattori, ChemMedChem 2008, 3, 1048-1060;
16. b) M. Porcelloni, P. D'Andrea, M. Altamura, R. M. Catalioto, S. Giuliani, S. Meini, D. Fattori, Bioorg. Med. Chem. Lett. 2008, 18, 4705-4707.
17. a) H. Y. Choi, D. Y. Chi, J. Am. Chem. Soc. 2001, 123, 9202-9203;
18. b) F. Effenberger, Angew. Chem. 2002, 114, 1775-1776;
19. Angew. Chem. Int. Ed. 2002, 41, 1699-700.
20. W. Adcock, P. R. Wells, Aust. J. Chem. 1965, 18, 1351-1364.
21. J. N. Kim, Y. J. Im, J. H. Gong, K. Y. Lee, Tetrahedron Lett. 2001, 42, 4195-4197.
22. 3 see:
23. a) L. E. J. Kennis, F. P. Bischoff, C. J. Mertens, C. J. Love, F. A. F. Van den Keybus, S. Pieters, M. Braeken, A. A. H. P. Megens, J. E. Leysen, Bioorg. Med. Chem. Lett. 2000, 10, 71-74;
24. b) J. Li, T. S. Rush III, W. Li, D. DeVincentis, X. Du, Y. Hu, J. R. Thomason, J. S. Xiang, J. S. Skotnicki, S. Tam, K. M. Cunningham, P. S. Chockalingam, E. A. Morris, J. I. Levin, Bioorg. Med. Chem. Lett. 2005, 15, 4961-4966.
25. C. Corey, S. Chaykovsky, Org. Synth. 1973, 5, 755-757.
26. J. Cossy, V. Bellosta, C. Hamoir, J.-R. Desmurs, Tetrahedron Lett. 2002, 43, 7083-7086.
27. C. P. Reddy, S. Tanimoto, Synthesis 1987, 575-577.
28. G. M. Rubottom, C. Kim, J. Org. Chem. 1983, 48, 1550 -1561.
29. a) V. Chaplinski, A. de Meijere, Angew. Chem. 1996, 108, 491-492;
30. Angew. Chem. Int. Ed. Engl. 1996, 35, 413 -414;
31. b) V. Chaplinski, H. Winsel, M. Kordes, A. de Meijere, Synlett 1997, 111-114;
32. O. G. Kulinkovich, A. de Meijere, Chem. Rev. 2000, 100, 2789-2834.
33. Y.-C. Cheng, W. H. Prusoff, Biochem. Pharmacol. 1973, 22, 3099-3108.
34. T. P. Kenakin, Pharmacologic Analysis of Drug-Receptor Interaction, 3rd ed., Lippincott-Raven, Philadelphia, 1997, pp. 331-373.