Synthesis and biological evaluation of imidazolo[2,1-b]benzothiazole derivatives, as potential p53 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 5, 2011, Pages 1649-1657

  Christodoulou, Michael S ^b   Colombo, Francesco ^a   Passarella, Daniele ^a   Ieronimo, Gabriella ^a   Zuco, Valentina ^c   De Cesare, Michelandrea ^c   Zunino, Franco ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^c NATIONAL CANCER INSTITUTE   (Italy)

Author keywords

Analogues of pifithrin ; Benzothiazole derivatives; Biochemical and biological evaluation; Combined treatment with taxanes; p53 Inhibitors; Tetrahydrobenzothiazole derivatives

Indexed keywords

4 (5',6',7',8' TETRAHYDROIMIDAZO[2,1 B]BENZOTHIAZOL 2' YL)BENZENAMINE; 4 (5',6',7',8' TETRAHYDROIMIDAZO[2,1 B]BENZOTHIAZOL 2' YL)BENZYLAMINE; 4 (IMIDAZO[2,1 B]BENZOTHIAZOL 2' YL)BENZYLAMINE; ANTINEOPLASTIC AGENT; BENZOTHIAZOLE DERIVATIVE; IMIDAZOLO[2,1 B]BENZOTHIAZOLE DERIVATIVE; P53 INHIBITOR; PACLITAXEL; PROTEIN P53; TUMOR SUPPRESSOR PROTEIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; OSTEOSARCOMA; OVARY CARCINOMA; PROTON NUCLEAR MAGNETIC RESONANCE; XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZOTHIAZOLES; CELL LINE, TUMOR; DISEASE MODELS, ANIMAL; FEMALE; GENE EXPRESSION REGULATION; HUMANS; INHIBITORY CONCENTRATION 50; OVARIAN NEOPLASMS; TOLUENE; TRANSPLANTATION, HETEROLOGOUS; TUMOR SUPPRESSOR PROTEIN P53;

EID: 79952188471     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.01.039     Document Type: Article

References (22)

1. L. Römer, C. Klein, A. Dehner, H. Kessler, and J. Buchner Angew. Chem., Int. Ed. 45 2006 6440
2. F. Toledo, and G.M. Wahl Nat. Rev. Cancer 6 2006 909
3. S. Haupt, M. Berger, Z. Goldberg, and Y.J. Haupt Cell Sci. 116 2003 4077
4. P. Perego, M. Giarola, S.C. Righetti, R. Supino, C. Caserini, D. Delia, M.A. Pierotti, T. Miyashita, J.C. Reed, and F. Zunino Cancer Res. 56 1996 556
5. M. Weller Cell Tissue Res. 292 1998 35
6. M. Laiho, and L. Latonen Ann. Med. 35 2003 391
7. R.H. Weiss Cancer Cell 4 2003 425
8. V. Zuco, and F. Zunino Neoplasia 10 2008 587
9. For the activity of pifithrin in the inhibition of p53 see: M.I. Walton, S.C. Wilson, I.R. Hardcastle, A.R. Mirza, and P. Workman Mol. Cancer Ther. 4 2005 1369
10. N. Pietrancosta, A. Moumen, R. Dono, P. Lingor, V. Planchamp, F. Lamballe, M. Bähr, J.L. Kraus, and F. Maina J. Med. Chem. 49 2006 3645
11. B. Sinn, J. Schulze, G. Schroeder, R. Konschak, D. Freyer, V. Budach, and I. Tinhofer Radiat. Res. 174 2010 601
12. F.J. Waters, T. Shavlakadze, M.J. McIldowie, M.J. Piggott, and M.D. Grounds Mol. Cell. Biochem. 337 2010 119
13. For previous synthesis of pifithrin and its analogs see: N. Pietrancosta, F. Maina, R. Dono, A. Moumen, C. Garino, Y. Laras, S. Burlet, G. Quéléver, and J.L. Kraus Bioorg. Med. Chem. Lett. 15 2005 1561
14. S.D. Carchéchath, R.I. Tawatao, M. Corr, D.A. Carson, and H.B. Cottam J. Med. Chem. 48 2005 6409
15. S. Murru, C.B. Singh, K. Veerababurao, and B.K. Patel Tetrahedron 64 2008 1931
16. Z. Wang, and Y. Sun Transl. Oncol. 3 2010 1
17. A.V. Gudkov, and E.A. Komarova Hum. Mol. Genet. 16 2007 R67
18. P.G. Komarov, E.A. Komarova, R.V. Kondratov, K. Christov-Tselkov, J.S. Coon, M.V. Chernov, and A.V. Gudkov Science 285 1999 1733
19. L.C. King, and R.J. Hlavacek J. Am. Chem. Soc. 72 1950 3722
20. I.V. Tetko, J. Gasteiger, R. Todeschini, A. Mauri, D. Livingstone, P. Ertl, V.A. Palyulin, E.V. Radchenko, N.S. Zefirov, A.S. Makarenko, V.Y. Tanchuk, and V.V. Prokopenko J. Comput. Aided Mol. Des. 19 2005 453
21. VCCLAB, Virtual Computational Chemistry Laboratory, http://www.vcclab. org.
22. I.V. Tetko Drug Discovery Today 10 2005 1497