Substituted E-3-(2-chloro-3-indolylmethylene)1,3-dihydroindol-2-ones with antitumor activity. Effect on the cell cycle and apoptosis

Journal of Medicinal Chemistry

Volumn 50, Issue 14, 2007, Pages 3167-3172

  Andreani, Aldo ^a   Burnelli, Silvia ^a   Granaiola, Massimiliano ^a   Leoni, Alberto ^a   Locatelli, Alessandra ^a   Morigi, Rita ^a   Rambaldi, Mirella ^a   Varoli, Lucilla ^a   Calonghi, Natalia ^a   Cappadone, Concettina ^a   Farruggia, Giovanna ^a   Zini, Maddalena ^a   Stefanelli, Claudio ^a   Masotti, Lanfranco ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 CHLORO 3 INDOLYLMETHYLENE) 1,3 DIHYDROINDOL 2 ONE DERIVATIVE; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG; VINCRISTINE SULFATE;

ALGORITHM; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE; CONTROLLED STUDY; CYTOSTASIS; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; GLIOMA CELL; GROWTH INHIBITION; HUMAN; HUMAN CELL; LUNG CANCER;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL DEATH; CELL DIVISION; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; OVARIAN NEOPLASMS;

EID: 34447542806     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070235m     Document Type: Article

References (25)

1. Potential Antitumor Agents 41. For part 40, see: Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi M.; Varoli, L.; Farruggia, G.; Stefanelli, C.; Masotti, L.; Kunkel, M. W. Synthesis and antitumor Activity of guanylhydrazones from 6-(2,4-dichloro-5-nitrophenyl) imidazo[2,1-b]thiazoles and 6-pyridylimidazo[2,1-b]thiazoles. J. Med. Chem. 2006, 49, 7897-7901.
2. Andreani, A.; Locatelli, A.; Rambaldi, M.; Leoni, A.; Bossa, R.; Fraccari, A.; Galatulas, I. Potential Antitumor Agents. 25. Synthesis and cytotoxic activity of 3-(2-chloro-3-indolylmethylene)1,3-dihydroindol-2-ones. Anticancer Res. 1996, 16, 3585-3588.
3. Andreani, A.; Locatelli, A.; Leoni, A.; Morigi, R.; Chiericozzi, M.; Fraccari, A.; Galatulas, I.; Salvatore, G. Synthesis and potential coanthracyclinic activity of pyridylmethylene and indolylmethylene lactams. Eur. J. Med. Chem. 1998, 33, 905-909.
4. Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Garaliene, V. Synthesis and antitumor activity of 1,5,6-substituted 3-(2-chloro-3-indolylmethylene) 1,3-dihydroindol-2-ones. J. Med. Chem. 2002, 45, 2666-2669.
5. Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Garaliene, V.; Farruggia, G.; Masotti, L. Substituted E-3-(2-chloro-3-indolylmethylene) 1,3-dihydroindol-2-ones with anti-tumor activity. Bioorg. Med. Chem. 2002, 12, 1121-1128.
6. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A. Feasibility of a high-flux anticancer drag screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. 1991, 83, 757-766.
7. Weinstein, J. N.; Myers, T. G.; O' Connor, P. M.; Friend, S. H.; Fornace, A. J., Jr.; Kohn, K. W.; Fojo, T.; Bates, S. E.; Rubinstein, L. V.; Anderson, N. L.; Boulamwini, J. K.; van Osdol, W. W.; Monks, A. P.; Scudiero, D. A.; Sausville, E. A.; Zaharevitz, D. W.; Bunow, B.; Viswanadhan, V. N.; Johnson, G. S.; Wittes, R. E.; Paull, K. D. An Information-intensive approach to the molecular pharmacology of cancer. Science 1997, 275, 343-349.
8. Paull, K. D.; Lin, C. M.; Malspeis, L.; Hamel, E. Identification of novel antimitotic agents acting at the tubulin level by computer-assisted evaluation of differential cytotoxicity data. Cancer Res. 1992, 52, 3892-3900.
9. Lambert, W. T.; Hanson, G. H.; Benayoud, F.; Burke, S. D. Halichondrin B: Synthesis of the C1-C22 subunit. J. Org. Chem. 2005, 70, 9382-9398.
10. Dabydeen, D. A.; Burnett, J. C.; Bai, R.; Verdier-Pinard, P.; Hickford, S. J.; Pettit, G. R.; Blunt, J. W.; Munro, M. H.; Gussio, R.; Hamel, E. Comparison of the activities of the truncated halichondrin B analog NSC 707389 (E7389) with those of the parent compound and a proposed binding site on tubulin. Mol. Pharmacol. 2006, 70, 1866-1875.
11. Hart, J. B.; Blunt, J. W.; Munro, M. H. Acid-catalyzed reactions of homohalichondrin B, a marine sponge-derived antitumor polyether macrolide. J. Org. Chem. 1996, 61, 2888-2890.
12. Fodstad, O.; Breistol, K.; Pettit, G. R.; Shoemaker, R. H.; Boyd, M. R. Comparative antitumor activities of halichondrins and vinblastine against human tumor xenografts. J. Exp. Ther. Oncol. 1996, 1, 119-125.
13. Luesch, H.; Moore, R. E.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H. Isolation of dolastatin 10 from the marine cyanobacterium symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1. J. Nat. Prod. 2001, 64, 907-910.
14. Kindler, H. L.; Tothy, P. K.; Wolff, R.; McCormack, R. A.; Abbruzzese, J. L.; Mani, S.; Wade-Oliver, K. T.; Vokes, E. E. Phase II trials of dolastatin-10 in advanced pancreaticobiliary cancers. Invest. New Drugs. 2005, 23, 489-493.
15. Lavrik, I. N.; Golks, A.; Krammer, P. H. Caspases: pharmacological manipulation of cell death. J. Clin. Invest. 2005, 115, 2665-2672.
16. Sosinski, J.; Thakar, J. H.; Germain, G. S.; Harwood, F. C.; Houghton, P. J. Proliferation-dependent and -independent cytotoxicity by antitumor diarylsulfonylureas. Indication of multiple mechanisms of drug action. Biochem. Pharmacol. 1993, 45, 2135-2142.
17. Xiang, X.; Saha, A. K.; Wen, R.; Ruderman, N. B.; Luo, Z. AMP-activated protein kinase activators can inhibit the growth of prostate cancer cells by multiple mechanisms. Biochem. Biophys. Res. Commun. 2004, 321, 161-167.
18. Brahimi, F.; Rachid, Z.; Qiu, Q.; McNamee, J. P.; Li, Y. J.; Tari, A. M.; Jean-Claude, B. J. Multiple mechanisms of action of ZR2002 in human breast cancer cells: A novel combi-molecule designed toblock signaling mediated by the ERB family of oncogenes and to damage genomic DNA. Int. J. Cancer 2004, 112, 484-491.
19. Haidara, K.; Zamir, L.; Shi, Q. W.; Batist, G. The flavonoid casticin has multiple mechanisms of tumor cytotoxicity action. Cancer Lett. 2006, 242, 180-190.
20. Qiu, Q.; Domarkas, J.; Banerjee, R.; Merayo, N.; Brahimi, F.; McNamee, J. P.; Gibbs, B. F.; Jean-Claude, B. J. The combi-targeting concept: In vitro and in vivo fragmentation of a stable combinitrosourea engineered to interact with the epidermal growth factor receptor while remaining DNA reactive. Clin. Cancer Res. 2007, 13, 331-340.
21. Zakrzewska, A.; Kolehmainen, E.; Osmialowski, B.; Gawinecki, R. 4-Fluoroanilines: Synthesis and decomposition. J. Fluorine Chem. 2001, 111, 1-10.
22. Romeo, A.; Corrodi, H.; Hardegger, E. The reaction of ethyl (o-nitrophenyl)acetate and (2-chloro-6-nitrophenyl)pyruvate. Helv. Chim. Acta 1955, 38, 463-467.
23. Beer, R. J. S.; Davenport, H. F.; Robertson, A. Extensions of the synthesis of hydroxyindoles from p-benzoquinones. J. Chem. Soc., Abstr. 1953, 1262-1264.
24. Mayer, F.; Oppenheimer, T. Naphthylacetic acids. III. 1-Nitronaphthyl-2-pyruvic acid and 1-nitronaphthyl-2-acetic acid. Chemische Berichte 1918, 51, 1239-1245.
25. Andreani, A.; Rambaldi, M.; Bonazzi, D.; Greci, L.; Andreani, F. Potential antitumor agents. III. Hydrazone derivatives of 5-substituted 2-chloro-3-formyl-6-methylindole. Farmaco 1979, 34, 132-138.