Insight into 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamides as peripheral benzodiazepine receptor ligands: Synthesis, biological evaluation and 3D-QSAR investigation

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 16, 2005, Pages 4821-4834

  Selleri, Silvia ^a   Gratteri, Paola ^a   Costagli, Camilla ^a   Bonaccini, Claudia ^a   Costanzo, Annarella ^a   Melani, Fabrizio ^a   Guerrini, Gabriella ^a   Ciciani, Giovanna ^a   Costa, Barbara ^b   Spinetti, Francesca ^b   Martini, Claudia ^b   Bruni, Fabrizio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

3D QSAR; Peripheral benzodiazepine receptor; Pyrazolo 1,5 a pyrimidines; Steroidogenesis assay

Indexed keywords

4' CHLORODIAZEPAM; 5,7 DIMETHYL 2 PHENYL 3 [(PIPERIDINOCARBONYL)METHYL]PYRAZOLO[1,5 A]PYRIMIDINE; 5,7 DIMETHYL 2 PHENYL 3 [(PYRROLIDINOCARBONYL)METHYL]PYRAZOLO[1,5 A]PYRIMIDINE; 5,7 DIMETHYL 3 [(4 METHYLPIPERAZINOCARBONYL)METHYL] 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDINE; ACETAMIDE DERIVATIVE; BENZODIAZEPINE RECEPTOR; ETHYL 5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YLACETATE; FUNCTIONAL GROUP; LIGAND; N ALPHA DIMETHYLBENZYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N BENZYL N ETHYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N ETHYL N ISOPROPYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N ETHYL N PHENYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N PROPYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N SEC BUTYL 1 (2 CHLOROPHENYL) N METHYL 3 ISOQUINOLINECARBOXAMIDE; N,N DI N BUTYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N,N DI N HEXYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N,N DI N OCTYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N,N DI N PENTYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N,N DI N PROPYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N,N DIBENZYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N,N DIETHYL 5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 CARBOXAMIDE; N,N DIETHYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)THIOACETAMIDE; N,N DIISOPROPYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; N,N DIMETHYL(5,7 DIMETHYL 2 PHENYLPYRAZOLO[1,5 A]PYRIMIDIN 3 YL)ACETAMIDE; STEROID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; GLIOMA CELL; MODULATION; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; RECEPTOR AFFINITY; STATISTICAL MODEL; STEROIDOGENESIS; SUBSTITUTION REACTION;

ACETAMIDES; ANIMALS; CELL LINE, TUMOR; CELLS, CULTURED; GLIOMA; KIDNEY; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, MOLECULAR; MOLECULAR PROBES; MOLECULAR STRUCTURE; PYRIMIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; RATS, WISTAR; RECEPTORS, GABA-A; STEROIDS;

EID: 21744438122     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.05.015     Document Type: Article

References (48)

1. M.W. McEnery, A.M. Snowman, R.R. Trifiletti, and S.H. Snyder Proc. Natl. Acad. Sci. U.S.A. 89 1992 3170
2. P. Casellas, S. Galiegue, and A.S. Basile Neurochem. Int. 40 2002 475
3. K.E. Krueger Biochim. Biophys. Acta 1241 1995 453
4. M. Gavish, I. Bachman, R. Shoukrun, Y. Katz, L. Veenman, G. Weisinger, and A. Weizman Pharmacol. Rev. 51 1999 629
5. G.B. O'Beirne, and D.C. Williams Eur. J. Biochem. 175 1988 413
6. S. Galiegue, N. Tinel, and P. Casellas Curr. Med. Chem. 10 2003 1563
7. L. Veenman, S. Leschiner, I. Spanier, G. Weisinger, A. Weizman, and M. Gavish J. Neurochem. 80 2002 917
8. A. Avital, G. Richter-Levin, S. Leschiner, I. Spanier, L. Veenman, A. Weizman, and M. Gavish Neuropsychopharmacology 25 2001 669
9. E. Kelly-Hershkovitz, R. Weizman, I. Spanier, S. Leschiner, M. Lahav, G. Weisinger, and M. Gavish J. Biol. Chem. 273 1998 5478
10. S. Lang Curr. Med. Chem. 9 2002 1411
11. T. Hauet, J. Liu, H. Li, M. Gazouli, M. Culty, and V. Papadopoulos Endocr. Res. 28 2002 395
12. J.J. Lacapere, and V. Papadopoulos Steroids 68 2003 569
13. J. Liu, H. Li, and V. Papadopoulos J. Steroid. Biochem. Mol. Biol 85 2003 275
14. M. Gazouli, Z. Han, and V. Papadopoulos J. Pharmacol. Exp. Ther. 303 2002 627
15. R. Farges, E. Joseph-Liauzun, D. Shire, D. Caput, G. Le Fur, and P. Ferrara Mol. Pharmacol. 46 1994 1160
16. A.A. Yeliseev, and S. Kaplan J. Biol. Chem. 274 1999 21234
17. V. Papadopoulos, H. Amri, N. Boujrad, C. Cascio, M. Culty, M. Garnier, M. Hardwick, H. Li, B. Vidic, A.S. Brown, J.L. Reversa, J.M. Bernassau, and K. Drieu Steroids 62 1998 21
18. N. Cinone, H.-D. Höltje, and A. Carotti J. Comput. Aided Drug Des. 14 2000 753
19. G. Campiani, V. Nacci, I. Fiorini, M.P. De Filippis, A. Garofalo, S.M. Ciani, G. Greco, E. Novellino, D.C. Williams, D.M. Zisterer, M.J. Woods, C. Mihai, C. Manzoni, and T. Mennini J. Med. Chem. 1996 3435
20. A. Cappelli, M. Anzini, S. Vomero, P.G. De Benedetti, M.C. Menziani, G. Giorgi, and C. Manzoni J. Med. Chem. 40 1997 2910
21. M. Anzini, A. Cappelli, S. Vomero, M. Seeber, M.C. Menziani, T. Langer, B. Hagen, C. Manzoni, and J.-J. Bourguignon J. Med. Chem. 44 2001 1134
22. S. Selleri, F. Bruni, C. Costagli, A. Costanzo, G. Guerrini, G. Ciciani, B. Costa, and C. Martini Bioorg. Med. Chem. 9 2001 2661
23. GOLPE 4.5. Multivariate Infometric Analysis Srl. (http://www.miasrl.com).
24. E.C. Taylor, G.H. Hawks, and A. McKillop J. Am. Chem. Soc. 90 1968 2421
25. T.S. Mansour Tetrahedron Lett. 29 1988 3437
26. M.F. Ansell Preparation of Acyl Halides 1972 Interscience London, Engl. 35 68
27. D.O. Jang, D.J. Park, and J. Kim Tetrahedron Lett. 40 1999 5323
28. P. Frøyen Synth. Commun. 25 1995 959
29. A.S. Ghozlan Said Pharmazie 46 1991 352
30. E. Romeo, J. Auta, A.P. Kozikowski, D. Ma, V. Papadopoulos, G. Puia, E. Costa, and A. Guidotti J. Pharmacol. Exp. Ther. 262 1992 971
31. G. Trapani, M. Franco, L. Ricciardi, A. Latrofa, G. Genchi, E. Sanna, F. Tuberi, E. Cagetti, G. Biggio, and G. Liso J. Med. Chem. 40 1997 3109
32. M.C. Dubroeucq, J. Benavides, A. Doble, F. Guillox, D. Allam, N. Vaucher, P. Bertran, C. Gueremy, C. Renault, and A. Uzan Eur. J. Pharmacol. 128 1986 269
33. A.H. Newman, H.W. Lueddens, P. Skolnick, and K.C. Rice J. Med. Chem. 30 1987 1901
34. F. Shah, S.P. Hume, V.W. Pike, S. Ashworth, and J. McDermott Nucl. Med. Biol. 21 1994 573
35. Selleri, S.; Bruni, F.; Costagli, C.; Costanzo, A.; Guerrini, G.; Ciciani, G.; Gratteri, P.; Besnard, F.; Costa, B.; Martini, C.; Fohlin, J.; De Siena, G.; Malmberg Aiello, P.; J. Med. Chem., submitted for publication.
36. P.J. Goodford J. Med. Chem. 28 1985 849
37. GRIDv.20 Molecular Discovery Ltd (http://www.moldiscovery.com ).
38. G. Trapani, M. Franco, A. Latrofa, L. Ricciardi, A. Carotti, M. Serra, E. Sanna, G. Biggio, and G. Liso J. Med. Chem. 42 1999 3934
39. G. Campiani, A. Ramunno, I. Fiorini, V. Nacci, E. Morelli, E. Novellino, M. Goegan, T. Mennini, S. Sullivan, D.M. Zisterer, and C.D. Williams J. Med. Chem. 45 2002 4276
40. G. Primofiore, F. Da Settimo, S. Taliani, F. Simorini, M.P. Patrizi, E. Novellino, G. Greco, E. Abignente, B. Costa, B. Chelli, and C. Martini J. Med. Chem. 45 2002 4276
41. InsightII 2000, Accelrys Inc. (www.accelrys.com).
42. (a) Volsurf v.3.0.11. (http://www.moldiscovery.com);
43. G. Cruciani, P. Crivori, P.-A. Carrupt, and B. Testa J. Mol. Struct. Theochem. 503 2000 17
44. Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099
45. O.H. Lowry, N.J. Rosenbrough, A.L. Farr, and R.J. Randall J. Biol. Chem. 193 1951 265
46. R.F. Squires, and C. Braestrup Nature 266 1997 732
47. M. Karobath, and G. Sperk Proc. Natl. Acad. Sci. U.S.A. 76 1979 1004
48. A. Costanzo, G. Guerrini, G. Ciciani, F. Bruni, S. Selleri, B. Costa, C. Martini, A. Lucacchini, P.M. Aiello, and A. Ipponi J. Med. Chem. 42 1999 2218