Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins. Part 2

Journal of Medicinal Chemistry

Volumn 54, Issue 9, 2011, Pages 3153-3162

  Combes, Sébastien ^a   Barbier, Pascale ^a   Douillard, Soazig ^a   McLeer Florin, Anne ^b   Bourgarel Rey, Véronique ^a   Pierson, Jean Thomas ^a   Fedorov, Alexey Yu ^c   Finet, Jean Pierre ^a   Boutonnat, Jean ^b   Peyrot, Vincent ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b GRENOBLE UNIVERSITY HOSPITAL   (France)

^c LOBACHEVSKY STATE UNIVERSITY OF NIZHNY NOVGOROD   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

4 (3' HYDROXY 4' METHOXYPHENYL) 5 METHOXYCOUMARIN; 4 (3' HYDROXY 4' METHOXYPHENYL) 5,6 DIMETHOXYCOUMARIN; 4 (3' HYDROXY 4' METHOXYPHENYL) 5,6,7 TRIMETHOXYCOUMARIN; 4 (3' HYDROXY 4' METHOXYPHENYL) 5,7 DIMETHOXYCOUMARIN; 4 (3' HYDROXY 4' METHOXYPHENYL) 6 METHOXYCOUMARIN; 4 (3' HYDROXY 4' METHOXYPHENYL) 6,7 DIMETHOXYCOUMARIN; 4 (3' HYDROXY 4' METHOXYPHENYL) 7 METHOXYCOUMARIN; 4 (3' HYDROXY 4' METHOXYPHENYL)COUMARIN; BREAKPOINT CLUSTER REGION PROTEIN; COMBRETASTATIN A4; COUMARIN DERIVATIVE; CYCLOSPORIN A; GLYCOPROTEIN P; METHOXYLATED 4 (3 HYDROXY 4 METHOXYPHENYL)COUMARIN; MITOXANTRONE; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CROSS COUPLING REACTION; CYTOTOXICITY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; ATP-BINDING CASSETTE TRANSPORTERS; CELL DIVISION; CELL LINE; CELL LINE, TUMOR; COUMARINS; CRYSTALLOGRAPHY, X-RAY; DAUNORUBICIN; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; G2 PHASE; HUMANS; MITOXANTRONE; MODELS, MOLECULAR; NEOPLASM PROTEINS; P-GLYCOPROTEIN; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

EID: 79955830810     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901826e     Document Type: Article

References (32)

1. Kingston, D. G. I. Tubulin-interactive natural products as anticancer agents J. Nat. Prod. 2009, 72, 507-515
2. Tozer, G. M.; Kanthou, C.; Parkins, C. S.; Hill, S. A. The biology of the combretastatins as tumour vascular targeting agents Int. J. Exp. Pathol. 2002, 83, 21-38 (Pubitemid 34638944)
3. Hinnen, P.; Eskens, F. A. L. M. Vascular disrupting agents in clinical development Br. J. Cancer 2007, 96, 1159-1165 (Pubitemid 46625071)
4. Kanthou, C.; Tozer, G. M. Tumour targeting by microtubule-depolymerising vascular disrupting agents Expert Opin. Ther. Targets 2007, 11, 1443-1457 (Pubitemid 350200480)
5. Banerjee, S.; Wang, Z.; Mohammad, M.; Sarkar, F. H.; Mohammad, R. M. Efficacy of selected natural products as therapeutic agents against cancer J. Nat. Prod. 2008, 71, 492-496 (Pubitemid 351549382)
6. Butler, M. S. Natural products to drugs: natural product-derived compounds in clinical trials Nat. Prod. Rep. 2008, 25, 475-516 (Pubitemid 351725315)
7. Bailly, C.; Bal, C.; Barbier, P.; Combes, S.; Finet, J.-P.; Hildebrand, M. P.; Peyrot, V.; Wattez, N. Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins J. Med. Chem. 2003, 46, 5437-5444 (Pubitemid 37490376)
8. Rappl, C.; Barbier, P.; Bourgarel-Rey, V.; Gregoire, C.; Gilli, R.; Carre, M.; Combes, S.; Finet, J.-P.; Peyrot, V. Interaction of 4-arylcoumarin analogues of combretastatins with microtubule network of HBL100 cells and binding to tubulin Biochemistry 2006, 45, 9210-9218 (Pubitemid 44156384)
9. Bai, R.; Covell, D. G.; Pei, X. F.; Ewell, J. B.; Nguyen, N. Y.; Brossi, A.; Hamel, E. Mapping the binding site of colchicinoids on beta-tubulin-2- chloroacetyl-2-demethylthiocolchicine covalently reacts predominantly with cysteine 239 and secondarily with cysteine 354 J. Biol. Chem. 2000, 275, 40443-40452 (Pubitemid 32064679)
10. Nguyen, T. L.; McGrath, C.; Hermone, A. R.; Burnett, J. C.; Zaharevitz, D. W.; Day, B. W.; Wipf, P.; Hamel, E.; Gussio, R. A common pharmacophore for a diverse set of colchicine site inhibitors using a structure-based approach J. Med. Chem. 2005, 48, 6107-6116 (Pubitemid 41324618)
11. Naumov, M. I.; Nuchev, A. V.; Sitnikov, N. S.; Malysheva, Y. B.; Shavyrin, A. S.; Beletskaya, I. P.; Gavryushin, A. E.; Combes, S.; Fedorov, A. Y. 2-(Azidomethyl)arylboronic acids in the synthesis of coumarin-type compounds Synthesis 2009, 10, 1673-1682
12. Ganina, O. G.; Daras, E.; Bourgarel-Rey, V.; Peyrot, V.; Andresuk, A. N.; Finet, J.-P.; Fedorov, A. Y.; Beletskaya, I. P.; Combes, S. Synthesis and biological evaluation of polymethoxylated 4-heteroarylcoumarins as tubulin assembly inhibitor Bioorg. Med. Chem. 2008, 16, 8806-8812
13. Luo, Y.; Wu, J. Palladium-catalyzed direct arylation of 4-hydroxycoumarins with arylboronic acids via C-OH bond activation Tetrahedron Lett. 2009, 50, 2103-2105
14. Wu, J.; Wang, L.; Fathi, R.; Yang, Z. Metal catalysed carbon-carbon bond-forming reaction Catalysts Fine Chem. Synth. 2004, 3, 64-67
15. Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J.; Rea, M. D. Synthesis of C-ring hydroxylated neoflavonoids by ligand coupling reactions Synth. Commun. 1999, 29, 2719-2730 (Pubitemid 29287931)
16. Billard, C.; Menasria, F.; Quiney, C.; Faussat, A. M.; Finet, J.-P.; Combes, S.; Kolb, J.-P. 4-Arylcoumarin analogues of combretastatins stimulate apoptosis of leukemic cells from chronic lymphocytic leukemia patients Exp. Hematol. 2008, 36, 1625-1633
17. Lage, H. An overview of cancer multidrug resistance: a still unsolved problem Cell. Mol. Life Sci. 2008, 65, 3145-3167
18. Wu, C. P.; Calcagno, A. M.; Ambudkar, S. V. Reversal of ABC drug transporter-mediated multidrug resistance in cancer cells: evaluation of current strategies Curr. Mol. Pharmacol. 2008, 1, 93-105
19. Heusele, C.; Bonne, D. Role of DAPI in microtubule reactions at steady-state Biochem. Biophys. Res. Commun. 1985, 133, 662-669 (Pubitemid 16103899)
20. Bonne, D.; Heusele, C.; Simon, C.; Pantaloni, D. 4′,6-Diamidino-2- phenylindole, a fluorescent probe for tubulin and microtubules J. Biol. Chem. 1985, 260, 2819-2825 (Pubitemid 15141425)
21. Lara-Ochoa, F.; Espinosa-perez, G. A new synthesis of combretastatins A-4 and AVE-8062A Tetrahedron Lett. 2007, 48, 7007-7010 (Pubitemid 47336949)
22. AMPAC 6.55; Semichem, Inc.: P.O. Box 1649, Shawnee, KS 66222, 1998.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
24. Cormier, A.; Marchand, M.; Ravelli, R. B. G.; Knossow, M.; Gigant, B. Structural insight into the inhibition of tubulin by vinca domain peptide ligands EMBO Rep. 2008, 9, 1101-1106
25. Boland, G. M.; Donnelly, D. M. X.; Finet, J.-P.; Rea, M. D. Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins J. Chem. Soc., Perkin Trans. 1 1996, 2591-2597 (Pubitemid 126803658)
26. Kym, P. R.; Iyengar, R.; Souers, A. J.; Lynch, J. K.; Judd, A. S.; Gao, J.; Freeman, J.; Mulhern, M.; Zhao, G.; Vasudevan, A.; Wodka, D.; Blackburn, C.; Brown, J.; Che, J. L.; Cullis, C.; Lai, S. J.; LaMarche, M. J.; Marsilje, T.; Roses, J.; Sells, T.; Geddes, B.; Govek, E.; Patane, M.; Fry, D.; Dayton, B. D.; Brodjian, S.; Falls, D.; Brune, M.; Bush, E.; Shapiro, R.; Knourek-Segel, V.; Fey, T.; McDowell, C.; Reinhart, G. A.; Preusser, L. C.; Marsh, K.; Hernandez, L.; Sham, H. L.; Collins, C. A. Discovery and characterization of aminopiperidinecoumarin melanin concentrating hormone receptor 1 antagonists J. Med. Chem. 2005, 48, 5888-5891 (Pubitemid 41324599)
27. Ciattini, P. G.; Morera, E.; Ortar, G. 4-Stannylcoumarins as useful reagents in a new approach to neoflavonoids Synth. Commun. 1995, 25, 2883-2894
28. Rizzi, E.; Dallavalle, S.; Merlini, L.; Pratesi, G.; Zunino, F. Short synthesis of cytotoxic 4-arylcoumarins Synth. Commun. 2006, 36, 1117-1122
29. Boumendjel, A.; McLeer-Florin, A.; Champelovier, P.; Allegro, D.; Muhammad, D.; Souard, F.; Derouazi, M.; Peyrot, V.; Toussaint, B.; Boutonnat, J. A novel chalcone derivative which acts as a microtubule depolymerising agent and an inhibitor of P-gp and BCRP in in vitro and in vivo glioblastoma models BMC Cancer 2009, 9, 242-253
30. Deesamer, S.; Kokpol, U.; Chavasiri, W.; Douillard, S.; Peyrot, V.; Vidal, N.; Combes, S.; Finet, J.-P. Synthesis and biological evaluation of isoflavone analogues from dalbergia oliveri Tetrahedron 2007, 63, 12986-12993 (Pubitemid 350116211)
31. Heusele, C.; Bonne, D.; Carlier, M. F. Is microtubule assembly a biphasic process - a flurometric study using 4′,6-diamidino-2-phenylindole as a probe Eur. J. Biochem. 1987, 165, 613-620 (Pubitemid 17090843)
32. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 1-496.