Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: Toward a structure/activity correlation

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 1, 2008, Pages 240-247

  Petrillo, Giovanni ^a   Mariggiò, Maria A ^b   Aiello, Cinzia ^c   Cordazzo, Cinzia ^c   Fenoglio, Carla ^d   Morganti, Stefano ^e   Croce, Michela ^c   Rizzato, Egon ^e   Spinelli, Domenico ^e   Maccagno, Massimo ^a   Bianchi, Lara ^a   Prevosto, Claudia ^c   Tavani, Cinzia ^a   Viale, Maurizio ^c  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF BARI   (Italy)

^c UNIVERSITY OF GENOA   (Italy)

^d UNIVERSITY OF PAVIA   (Italy)

^e UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Antiproliferative activity; Mechanism of action; Molecular simplification strategy; Naphthylnitrobutadienes

Indexed keywords

1,3 BUTADIENE; 1,4 BIS(1 NAPHTHYL) 2,3 DINITRO 1,3 BUTADIENE; 1,4 BIS(4 CARBOXY 1 NAPHTHYL) 2,3 DINITRO 1,3 BUTADIENE; METHYL 2 METHYLSULFANYL 5 (1 NAPHTHYL) 4 NITRO 2,4 PENTADIENOATE; NAPHTHYL GROUP; NITRO DERIVATIVE; PROTEIN P53; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG DNA BINDING; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BUTADIENES; CELL LINE, TUMOR; CELL PROLIFERATION; DNA; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; INTERPHASE; NAPHTHALENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR SUPPRESSOR PROTEIN P53;

EID: 38049178571     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.09.042     Document Type: Article

References (26)

1. Neidle S., and Thurston D.E. Nat. Rev. Cancer 5 (2005) 285-296
2. Pujol M.D., Romero M., and Sanchez I. Curr. Med. Chem. Anticancer Agents 5 (2005) 215-237
3. Medarde M., Maya A.B., and Perez-Melero C. J. Enzyme Inhib. Med. Chem. 19 (2004) 521-540
4. Alessio E., Mestroni G., Bergamo A., and Sava G. Curr. Top. Med. Chem. 4 (2004) 1525-1535
5. Schwartsmann G., Ratain M.J., Cragg G.M., Wong J.E., Saijo N., Parkinson D.R., Fujiwara Y., Pazdur R., Newman D.J., Dagher R., and Di Leone L. J. Clin. Oncol. 20 (2002) 47S-59S
6. Pakin D.M. Lancet Oncol. 2 (2001) 533-543
7. Ferlay, J.; Bray, F.; Pisani, P.; Parkin, D. M. Globocan 2000: cancer incidence, mortality and prevalence worldwide, version 1.0 (IARC, CancerBase No 5). IARC Press, Lyon, 2001.
8. Viale M., Ottone M., Chiavarina B., Mariggiò M.A., Prevosto C., Dell'Erba C., Petrillo G., and Novi M. Invest. New Drug 22 (2004) 359-367
9. Novi M., Ottone M., Dell'Erba C., Barbieri F., Chiavarina B., Maccagno M., and Viale M. Oncol. Rep. 12 (2004) 91-96
10. Dell'Erba C., Chiavarina B., Fenoglio C., Petrillo G., Cordazzo C., Boncompagni E., Spinelli D., Ognio E., Aiello C., Mariggiò M.A., and Viale M. Pharmacol. Res. 52 (2005) 271-282
11. Dell'Erba C., Mele A., Novi M., Petrillo G., and Stagnaro P. Tetrahedron Lett. 31 (1990) 4933-4936
12. Dell'Erba C., Mele A., Novi M., Petrillo G., and Stagnaro P. Tetrahedron 48 (1992) 4407-4418
13. Bianchi L., Dell'Erba C., Maccagno M., Morganti S., Petrillo G., Rizzato E., Sancassan F., Severi E., Spinelli D., and Tavani C. Arkivoc vii (2006) 169-185
14. Dell'Erba C., Gabellini A., Novi M., Petrillo G., Tavani C., Cosimelli B., and Spinelli D. Tetrahedron 57 (2001) 8159-8165
15. Gonzales V.M., Fuertes M.A., Alonso C., and Perez J.M. Mol. Pharmacol. 59 (2001) 657-663
16. Pérez J.M., Montero E.I., González A.M., Alvarez-Valdés A., Alonso C., and Navarro-Ranninger C. J. Inorg. Biochem. 77 (1999) 37-42
17. Geske F.J., and Gerschenson L.E. Hum. Pathol. 32 (2001) 1029-1038
18. Kerr J.F.R., Winterford C.M., and Harmon B.V. Cancer 73 (1994) 2013-2026
19. Green A.M., and Steinmetz N.D. Cancer J. 8 (2002) 82-92
20. Gadducci A., Cosio S., Muraca S., and Genazzani A.R. Eur. J. Gynaecol. Oncol. 23 (2002) 390-396
21. Manetti D., Ghelardini C., Bartolini A., Dei S., Galeotti N., Gualtieri F., Romanelli M.N., and Teodori E. J. Med. Chem. 43 (2000) 4499-4507
22. Crisòstomo F.R.P., Carrillo R., Leòn L.G., Marti{dotless}̀n T., Padròn J.M., and Martin V.S. J. Org. Chem. 71 (2006) 2339-2345
23. Goldstein H., Mohr R., and Blezinger T. Helv. Chim. Acta 18 (1935) 813-816
24. Boymond L., Rottlander M., Cahiez G., and Knochel P. Angew. Chem. Int. Ed. Engl. 110 (1998) 1801-1804
25. Hussain R.F., Nouri A.M.E., and Oliver R.T.D. J. Immunol. Methods 160 (1993) 89-96
26. Coluccia M., Boccarelli A., Mariggiò M.A., Cardellicchio N., Caputo P., Intini F.P., and Natile G. Chem. Biol. Interact. 98 (1995) 251-266