Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity

European Journal of Medicinal Chemistry

Volumn 46, Issue 11, 2011, Pages 5293-5309

  Balbi, Alessandro ^a   Anzaldi, Maria ^a   MacCi, Chiara ^a   Aiello, Cinzia ^b   Mazzei, Mauro ^a   Gangemi, Rosaria ^b   Castagnola, Patrizio ^b   Miele, Mariangela ^a   Rosano, Camillo ^b   Viale, Maurizio ^b  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF GENOA   (Italy)

Author keywords

Antitumor activity; Apoptosis; Pyrazole derivatives; Tubulin polymerization inhibitors

Indexed keywords

1 (3 CHLOROPHENYL) 5 (2,6,6 TRIMETHYL 2 CYCLOHEX 1 YL)ETHENYL 1H PYRAZOLE; 1 (3,4 DIMETHYLPHENYL) 5 (2,6,6 TRIMETHYL 2 CYCLOHEX 1 YL)ETHENYL 1H PYRAZOLE; 1 (4 CHLOROPHENYL) 5 (4 METHOXYPHENYL) 1H PYRAZOLE; 1 (4 METHOXYPHENYL) 5 (2,6,6 TRIMETHYL 2 CYCLOHEX 1 YL)ETHENYL 1H PYRAZOLE; 1 BENZYL 5 (2,6,6 TRIMETHYL 2 CYCLOHEX 1 YL)ETHENYL 1H PYRAZOLE; 2 (5 (1 (2,6,6 TRIMETHYLCYCLOHEX 2 ENYL)PROP 1 EN 2 YL) 1H PYRAZOL 1 YL)PYRIDINE; 2 [1 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 4 METHYLPHENOL; 2 [1 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL] 5 METHOXYPHENOL; 2 [3 (4 METHOXYPHENYL) 1H PYRAZOL 1 YL]PYRIDINE; 2 [5 (4 METHOXYPHENYL) 1H PYRAZOL 1 YL]PYRIDINE; 2 [5 [2 (2,6,6 TRIMETHYLCYCLOHEX 2 ENYL)VINYL]PYRAZOL 1 YL]PYRIDINE; 2 [5 [2 (3 CHLOROPHENYL)VINYL]PYRAZOL 1 YL]PYRIDINE; 2 [5 [2 (3,4 DIMETHOXYPHENYL)VINYL]PYRAZOL 1 YL]PYRIDINE; 2 [5 [2 (4 CHLOROPHENYL)VINYL]PYRAZOL 1 YL]PYRIDINE; 2 [5 [2 (FURAN 2 YL)VINYL] 1H PYRAZOL 1 YL]PYRIDINE; 2 [5 [2 (PHENYL)VINYL]PYRAZOL 1 YL]PYRIDINE; 4 CHLORO 2 [1 (4 CHLOROPHENYL) 1H PYRAZOL 5 YL]PHENOL; 4 CHLORO 2 [1 (PYRIDIN 2 YL) 1H PYRAZOL 3 YL]PHENOL; 4 CHLORO 2 [1 (PYRIDIN 2 YL) 1H PYRAZOL 5 YL]PHENOL; 5 (2,6,6 TRIMETHYL 2 CYCLOHEXEN 1 YL)ETHENYL 1H PYRAZOLE 1 THIOCARBOXAMIDE; 5 METHOXY 2 [1 (PYRIDIN 2 YL) 1H PYRAZOL 3 YL]PHENOL; 5 METHOXY 2 [1 (PYRIDIN 2 YL) 1H PYRAZOL 5 YL]PHENOL; ETHYL 2 [5 [2 (2,6,6 TRIMETHYLCYCLOHEXEN 2 YL)VINYL] 1H PYRAZOL 1 YL]ETHANOATE; N [4 [(1 (PYRIDIN 2 YL) 1H PYRAZOL 5 YL)]PHENYL]ETHANAMIDE; PACLITAXEL; PROTEIN P21; PROTEIN P53; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINCRISTINE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; LUNG CARCINOMA; NONHUMAN; OVARY ADENOCARCINOMA; POLYPLOIDY; PROTEIN EXPRESSION; WESTERN BLOTTING;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CELL NUCLEUS; CELL PROLIFERATION; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIN-DEPENDENT KINASE INHIBITOR P21; DRUG EVALUATION, PRECLINICAL; HUMANS; INDOLES; MICE; MICROTUBULES; MODELS, MOLECULAR; PROTEIN MULTIMERIZATION; PROTEIN STRUCTURE, QUATERNARY; PYRAZOLES; TUBULIN; TUMOR SUPPRESSOR PROTEIN P53;

EID: 80054890054     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.08.014     Document Type: Article

References (53)

1. J. Elguero, P. Goya, N. Jagerovic, and A.M.S. Silva O.A. Attanasi, D. Spinelli, Targets in Heterocyclic Systems 6th ed 2002 Societ Chimica Italiana Roma 52 98
2. G. Szabo, J. Fischer, A. Kis-Varga, and K. Gyires J. Med. Chem. 51 2008 142 147
3. A. Tanitame, Y. Oyamada, K. Ofuji, H. Terauchi, M. Kawasaki, M. Wachi, and J. Yamagishi Bioorg. Med. Chem. Lett. 15 2005 4299 4303
4. A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, K. Suzuki, T. Ueda, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi, and J. Yamagishi Bioorg. Med. Chem. 12 2004 5515 5524
5. N. Cho, M. Kamaura, T. Yogo, and H. Imoto PCT Int. Appl. 2009 WO 2009139340
6. K. Dugi, M. Mark, and F. Himmelsbach PCT Int. Appl. 2009 WO 2009022009
7. Y. Momose, T. Maekawa, H. Odaka, and H. Kimura PCT Int. Appl. 2001 WO 2001038325
8. S.M. Rida, M.N.S. Saudi, A.M. Youssef, and M.A. Halim Lett. Org. Chem. 6 2009 282 288
9. J. Regan, S. Breitfelder, P. Cirillo, T. Gilmore, A.G. Graham, E. Hickey, B. Klaus, J. Madwed, M. Moriak, N. Moss, C. Pargellis, S. Pav, A. Proto, A. Swinamer, L. Tong, and C. Torcellini J. Med. Chem. 45 2002 2994 3008
10. M.G. Brasca, C. Albanese, R. Amici, D. Ballinari, L. Corti, V. Croci, D. Fancelli, F. Fiorentini, M. Nesi, P. Orsini, F. Orzi, W. Pastori, E. Perrone, E. Pesenti, P. Pevarello, F. Riccardi-Sirtori, F. Roletto, P. Roussel, M. Varasi, A. Vulpetti, and C. Mercurio Chem. Med. Chem. 2 2007 841 852
11. P. Pevarello, D. Fancelli, A. Vulpetti, R. Amici, M. Villa, V. Pittal, P. Vianello, A. Cameron, M. Ciomei, C. Mercurio, J.R. Bischoff, F. Roletto, M. Varasi, and M.G. Brasca Bioorg. Med. Chem. Lett. 16 2006 1084 1090
12. A.H. Abadi, A. Abdel Haleem Eissa Hassan, and G.S. Hassan Chem. Pharm. Bul 51 2003 838 844
13. M.R. Michaelides PCT Int. Appl. 2010 WO 2010065825
14. S. Ludwig, O. Planz, Hans-H. Sedlacek, and S. Pleschka PCT Int. Appl. 2004 WO 2004085682
15. E.M. Perchellet, M.M. Ward, Alexios-L. Skaltsounis, I.K. Kostakis, N. Pouli, P. Marakos, and J.H. Perchellet Anticancer Res. 26 2006 2791 2804
16. B. Insuasty, A. Tigreros, F. Orozco, J. Quiroga, R. Abonia, M. Nogueras, A. Sanchez, and J. Cobo Bioorg. Med. Chem. 18 2010 4965 4974
17. M. Labbozzetta, R. Baruchello, P. Marchetti, M.C. Gueli, P. Poma, M. Notarbartolo, D. Simoni, and N. D'Alessandro Chem.-Biol. Interact 181 2009 29 36
18. P. Pevarello, M.G. Brasca, R. Amici, P. Orsini, G. Traquandi, L. Corti, C. Piutti, P. Sansonna, M. Villa, B.S. Pierce, M. Pulici, P. Giordano, K. Martina, E.L. Fritzen, R.A. Nugent, E. Casale, A. Cameron, M. Ciomei, F. Roletto, A. Isacchi, G.P. Fogliatto, E. Pesenti, W. Pastori, A. Marsiglio, K.L. Leach, P.M. Clare, F. Fiorentini, M. Varasi, A. Vulpetti, and M.A. Warpehoski J. Med. Chem. 47 2004 3367 3380
19. M. Anzaldi, E. Sottofattori, R. Rizzetto, B. Granello Di Casaleto, and A. Balbi Eur. J. Med. Chem. 34 1999 837 842
20. A. Balbi, M. Anzaldi, M. Mazzei, M. Miele, M. Bertolotto, L. Ottonello, and F. Dallegri Bioorg. Med. Chem. 14 2006 5152 5160
21. M. Anzaldi, C. Macci, M. Mazzei, M. Bertolotto, L. Ottonello, F. Dallegri, and A. Balbi Chem. Biodivers 6 2009 1674 1687
22. S. Al-Mousawi, M.M. Abdel-Khalik, S. El-Sherbiny, E. John, and M.H. Elnagdi J. Heterocycl. Chem. 38 2001 949 953
23. Y. Lin, and S.A. Lang Jr. J. Org. Chem. 45 1980 4857 4860
24. T. Ghosh, S. Saha, and C. Bandyopadhyay Synthesis 11 2005 1845 1849
25. W. Loewe, and A. Kennemann Arch. Pharm. 318 1985 239 243
26. J.P. Dusza, A.S. Tomcufcik, and J.D. Albright Eur. Pat. Appl. 1985 EP 129847
27. C.K. Ghosh, and S. Khan Synthesis 9 1981 719 721
28. S.S. Tseng, J.W. Epstein, H.J. Brabander, and G. Francisco J. Heterocycl. Chem. 24 1987 837 843
29. S.S. Tseng, J.P. Dusza, and J.W. Epstein U. S. P. 1989 US 4888345
30. Y.D. Wang, A. Gopalsamy, D.W. Powell, H. Tsou, and N. Zhang U. S. Pat. Appl. 2006 20060063785
31. A.M.S. Silva, L.M.P.M. Almeida, J.A.S. Cavaleiro, C. Foces-Foces, A.L. Llamas-Saiz, C. Fontenas, N. Jagerovic, and J. Elguero Tetrahedron 53 1997 11645 11658
32. G.A. Reynolds, J.A. Van Allan, and A.K. Seidel J. Heterocycl. Chem. 16 1979 369 370
33. J.C. Jung Lee, J.H. Lee, S. Oh, J.G. Lee, and O.S. Park Bioorg. Med. Chem. Lett. 14 2004 5527 5531
34. S.S. Jenkins J. Am. Chem. Soc. 54 1932 1155 1163
35. E. Hasegawa, K. Ishiyama, T. Horaguchi, and T. Shimizu J. Org. Chem. 56 1991 1631 1635
36. A. Horeau, and J. Jacques Bull. Soc. Chim. Fr. 1948 53 59
37. M.A. Jordan, D. Thrower, and L. Wilson J. Cell Sci. 102 1992 401 416
38. E.L.K. Goh, T.J. Pircher, and P.E. Lobie Endocrinology 139 1998 4364 4372
39. B. Gigant, C. Wang, R.B. Ravelli, F. Roussi, M.O. Steinmetz, P.A. Curmi, A. Sobel, and M. Knossow Nature 435 2005 519 522
40. H. Ohki, K. Hirotani, H. Naito, S. Ohsuki, M. Minami, A. Ejima, Y. Koisoc, and Y. Hashimoto Bioorg. Med. Chem. Lett. 12 2002 3191 3193
41. M. Iwahana, Y. Ochi, and A. Ejima Anticancer Res. 20 2000 785 792
42. C. Wasylyk, H. Zheng, C. Castell, L. Debussche, M.C. Multon, and B. Wasylyk Cancer Res. 68 2008 1275 1283
43. S. Bergemann, R. Brecht, F. Büttner, D. Guénard, R. Gust, G. Seitz, M.T. Stubbs, and S. Thoret Bioorg. Med. Chem. 11 2003 1269 1281
44. V. Agnese, V. Bazan, F.P. Fiorentino, D. Fanale, G. Badalamenti, G. Colucci, V. Adamo, D. Santini, and A. Russo Ann. Oncol. 18 2007 47 52 Supp vi
45. J.R. Pollard, and M. Mortimore J. Med. Chem. 52 2009 2629 2651
46. D.O. Wise, R. Krahe, and B.R. Oakley Genomics 67 2000 164 170
47. T. Nayak, H. Edgerton-Morgan, T. Horio, Y. Xiong, C.P. De Souza, S.A. Osmani, and B.R. Oakley J. Cell. Biol. 190 2010 317 330
48. S. Cafaggi, E. Russo, R. Stefani, R. Leardi, G. Caviglioli, B. Parodi, G. Bignardi, D. De Totero, C. Aiello, and M. Viale J. Control. Release 121 2007 110 123
49. R.F. Hussain, A.M.E. Nouri, and R.T.D. Oliver J. Immunol. Methods 160 1993 89 96
50. D. Bonne, C. Heusele, C. Simon, and D. Pantaloni J. Biol. Chem. 260 1985 2819 2825
51. D.M. Barron, S.K. Chatterjee, R. Ravindra, R. Roof, E. Baloglu, G.I. David, D.G.I. Kingston, and S. Bane Anal. Biochem. 315 2003 49 56
52. M.F. Sanner, B.S. Duncan, C.J. Carrillo, and A.J. Olson Symp. Biocomput 4 1999 401 412
53. D.S. Goodsell, G.M. Morris, and A.J. Olson J. Mol. Recognit 9 1996 1 5