Synthesis and antiproliferative activity of 3-(2-chloroethyl)-5-methyl-6-phenyl-8-(trifluoromethyl)-5,6-dihydropyrazolo[3,4-f][1,2,3,5]tetrazepin-4-(3H)-one

European Journal of Medicinal Chemistry

Volumn 96, Issue , 2015, Pages 98-104

  Maggio, Benedetta ^a   Raimondi, Maria Valeria ^a   Raffa, Demetrio ^a   Plescia, Fabiana ^a   Cascioferro, Stella ^a   Cancemi, Gabriella ^a   Tolomeo, Manlio ^a   Grimaudo, Stefania ^a   Daidone, Giuseppe ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 CHLOROETHYL) 5 METHYL 6 PHENYL 8 (TRIFLUOROMETHYL) 5,6 DIHYDROPYRAZOLO[3,4 F][1,2,3,5]TETRAZEPIN 4 (3H) ONE; 3,5 DIMETHYL 6 PHENYL 8 (TRIFLUOROMETHYL) 5,6 DIHYDROPYRAZOLO{3,4 F][1,2,3,5]TETRAZEPIN 4 (3H) ONE; ANTINEOPLASTIC AGENT; DAUNORUBICIN; DOUBLE STRANDED DNA; ETOPOSIDE; HETEROCYCLIC COMPOUND; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; MULTIDRUG RESISTANCE PROTEIN; TEMOZOLOMIDE; UNCLASSIFIED DRUG; 3-(2-CHLOROETHYL)-5-METHYL-6-PHENYL-8-(TRIFLUOROMETHYL)-5,6-DIHYDROPYRAZOLO(3,4-F)(1,2,3,5)TETRAZEPIN-4-(3H)-ONE; AZEPINE DERIVATIVE; PYRAZOLE DERIVATIVE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL DEATH; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; G1 PHASE CELL CYCLE CHECKPOINT; GENE OVEREXPRESSION; HEPG2 CELL LINE; HL 60 CELL LINE; HUMAN; HUMAN CELL; K562 CELL LINE; MINIMAL RESIDUAL DISEASE; PHENOTYPE; PROTON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; APOPTOSIS; AZEPINES; CELL CYCLE; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; K562 CELLS; MOLECULAR STRUCTURE; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84927130269     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.04.004     Document Type: Article

References (20)

1. J.L. Villano, N. Letarte, L.R. Bressler, Going past the data for temozolomide, Cancer Chemother. Pharmacol. 69 (2012) 1113-1115.
2. J.A.B. van Genugten, P. Leffers, B.G. Baumert, H. Tjon-a-Fat, A. Twijnstra, Effectiveness of temozolomide for primary glioblastoma multiforme in routine clinical practice, J. Neuro-oncol. 96 (2010) 249-257.
3. K.J. Cohen, I.F. Pollack, T. Zhou, A. Buxton, E.J. Holmes, P.C. Burger, D.J. Brat, M.K. Rosenblum, R.L. Hamilton, R.S. Lavey, R.L. Heideman, Temozolomide in the treatment of high-grade gliomas in children: a report from the Children's oncology Group, Neuro-Oncol. 13 (2011) 317-323.
4. M. Reni, F. Zaja, W. Mason, J. Perry, E. Mazza, M. Spina, R. Bordonaro, F. Ilariucci, M. Faedi, G. Corazzelli, P. Manno, E. Franceschi, A. Pace, M. Candela, A. Abbadessa, C. Stelitano, G. Latte, A.J.M. Ferreri, Temozolomide as salvage treatment in primary brain lymphomas, Brit. J. Cancer 96 (2007) 864-867.
5. R. Dubrow, A.S. Darefsky, D.I. Jacobs, L.S. Park, M.G. Rose, M.S.H. Maxwell, J.T. King Jr., Time trends in glioblastoma multiforme survival: the role of temozolomide, Neuro-Oncol. 15 (2013) 1750-1761.
6. T. Yamaki, Y. Suenaga, T. Iuchi, J. Alagu, A. Takatori, M. Itami, A. Araki, M. Ohira, M. Inoue, H. Kageyama, S. Yokoi, N. Saeki, A. Nakagawara, Temozolomide suppresses MYC via activation of TAp63 to inhibit progression of human glioblastoma, Sci. Rep. 3 (2013) 1160.
7. S.D. Baker, M. Wirth, P. Statkevich, P. Reidenberg, K. Alton, S.E. Sartorius, M. Dugan, D. Cutler, V. Batra, L.B. Grochow, R.C. Donehower, E.K. Rowinsky, Absorption, metabolism, and excretion of 14C-temozolomide following oral administration to patients with advanced cancer, Clin. Cancer Res. 5 (1999) 309-317.
8. W. Wick, M.l. Platten, M. Weller, New (alternative) temozolomide regimens for the treatment of glioma, Neuro-Oncol. 11 (2009) 69-79.
9. I. Passagne, A. Evrard, P. Depeille, P. Cuq, D. Cupissol, L. Vian, O6-methylguanine-DNA methyltransferase (MGMT) overexpression in melanoma cells induces resistance to nitrosoureas and temozolomide but sensitizes to mitomycin C, Toxicol. Appl. Pharm. 211 (2006) 97-105.
10. C.H. Fan, W.L. Liu, H. Cao, C. Wen, L. Chen, G. Jiang, O6-methylguanine-DNA methyltransferase as a promising target for the treatment of temozolomideresistant gliomas, Cell. Death Dis. 4 (2013) e876.
11. B.J. Jean-Claude, A. Mustafa, A. Watson, Z. Damian, D.E. Vasilescu, T.H. Chan, B. Leyland-Jones, Tetrazepinones are equally cytotoxic to Mer\+ and merhuman tumor cell lines, J. Pharm. Exp. Ther. 288 (1999) 484-489.
12. B.J. Jean-Claude, A. Mustafa, Z. Damian, J. De Marte, D.E. Vasilescu, R. Yen, T.H. Chan, B. Leyland-Jones, Cytokinetics of a novel 1, 2, 3-triazene-containing heterocycle, 8-nitro-3-methyl-benzo-1, 2, 3, 5-tetrazepin-4(3H)-one (NIME), in the human epithelial ovarian cancer cell line OVCAR-3, Biochem. Pharm. 57 (1999) 753-762.
13. B.J. Jean-Claude, G. Just, Synthesis of bi-and tri-cyclic tetrazepinones, J. Chem. Soc. Perkin Trans. 1 10 (1991) 2525-2529.
14. B.J. Jean-Claude, A. Mustafa, N.D. Cetateanu, Z. Damian, J. De Marte, R. Yen, D. Vasilescu, T.H. Chan, B. Leyland-Jones, Design and mechanism of action of a novel cytotoxic 1, 2, 3-triazene-containing heterocycle, 3, 5-dimethyl-pyrido-1, 2, 3, 5-tetrazepin-4-one (PYRZ), in the human epithelial ovarian cancer cell line NIH: OVCAR-3 in vitro, Br. J. Cancer 76 (1997) 467-473.
15. B.D. Hornebeck, Y.N. Strube, D. Vasilescu, B.J. Jean-Claude, Design and synthesis of a novel water soluble benzotetrazepinone, Bioorg. Med. Chem. Lett. 10 (2000) 2325-2327.
16. B. Maggio, D. Raffa, M.V. Raimondi, F. Plescia, S. Cascioferro, G. Daidone, Synthesis of alkyl-5, 8-dimethyl-6-phenyl-5, 6-dihydropyrazolo [3, 4-f] [1, 2, 3, 5] tetrazepin-4(3H)-ones of pharmaceutical interest, Arkivoc xvi (2006) 120-126.
17. B. Maggio, D. Raffa, M.V. Raimondi, S. Cascioferro, F. Plescia, M. Tolomeo, E. Barbusca, G. Cannizzo, S. Mancuso, G. Daidone, Synthesis and induction of G0-G1 phase arrest with apoptosis of 3, 5-Dimethyl-6-phenyl-8-(trifluoromethyl)-5, 6-dihydropyrazolo [3, 4-f] [1, 2, 3, 5]tetrazepin-4(3H)-one, Eur. J. Med. Chem. 43 (2008) 2386-2394.
18. R.I. Freshney, Culture of Animal Cells. A Manual of Basic Technique, second ed., Alan R. Liss, New York, 1987, p. 117.
19. R.C. Duke, J.J. Cohen, Morphological and biochemical assays of apoptosis, in: J.E. Coligan, A.M. Kruisbeek, D.H. Margulies, E.M. Shevach, W. Strober (Eds.), Current Protocols in Immunology, Greene Publishing and Wiley-Interscience, New York, 1992, pp. 1-16 unit 3.17.
20. M.G. Ormerod, B. Tribukait, W. Giarretti, Consensus report of the task force on standardisation of DNA flow cytometry in clinical pathology, Anal. Cell. Path 17 (1998) 103-110.