Design, synthesis and anticancer properties of 5-arylbenzoxepins as conformationally restricted isocombretastatin A-4 analogs

European Journal of Medicinal Chemistry

Volumn 62, Issue , 2013, Pages 28-39

  Rasolofonjatovo, Evelia ^a   Provot, Olivier ^a   Hamze, Abdallah ^a   Rodrigo, Jordi ^a   Bignon, Jérome ^b   Wdzieczak Bakala, Joanna ^b   Lenoir, Christine ^b   Desravines, Déborah ^b   Dubois, Joëlle ^b   Brion, Jean Daniel ^a   Alami, Mouad ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

Apoptosis; Benzoxepin; Cancer; Combretastatin; Cytotoxicity; isoCA 4; Tubulin

Indexed keywords

5 ARYLBENZOXEPINS; 8 METHOXY 5 (3,4,5 TRIMETHOXYPHENYL) 2,3 DIHYDROBENZO[B]OXEPIN 9 OL; ANTINEOPLASTIC AGENT; BENZOXEPIN DERIVATIVE; BETA TUBULIN; COLCHICINE; COMBRETASTATIN A4; IODIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BINDING SITE; CANCER CELL; CELL ASSAY; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; ISOMER; MICROTUBULE ASSEMBLY; MOLECULAR DOCKING;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; BENZOXEPINS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84872685378     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.12.042     Document Type: Article

References (73)

1. G.R. Pettit, S.B. Singh, E. Hamel, C.M. Lin, D.S. Alberts, and D. Garcia-Kendall Experientia 45 1989 209 211
2. G.R. Pettit, M.R. Rhodes, D.L. Herald, E. Hamel, J.M. Schmidt, and R.K. Pettit J. Med. Chem. 48 2005 4087 4099
3. A.T. Mc Gown, and B.W. Fox Cancer Chemother. Pharmacol. 26 1990 79 81
4. G.R. Pettit, B. Toki, D.L. Herald, P. Verdier-Pinard, M.R. Boyd, E. Hamel, and R.K. Pettit J. Med. Chem. 41 1998 1688 1695
5. D.J. Chaplin, G.R. Pettit, and S.A. Hill Anticancer Res. 19 1999 189 195
6. D.J. Chaplin, and S.A. Hill Int. J. Radiat. Oncol. Biol. Phys. 54 2002 1491 1496
7. G.R. Pettit, C. Temple, V.L. Narayanan, R. Varma, M.R. Boyd, G.A. Rener, and N. Bansal Anti-Cancer Drug Des. 10 1995 299 309
8. G.J. Rustin, S.M. Galbraith, H. Anderson, M. Stratford, L.K. Folkes, L. Sena, L. Gumbrell, and P.M. Price J. Clin. Oncol. 21 2003 2815 2822
9. A. Dowlati, K. Robertson, M. Cooney, W.P. Petros, M. Stratford, J. Jesberger, N. Rafie, B. Overmoyer, V. Makkar, B. Stambler, A. Taylor, J. Waas, J.S. Lewin, K.R. McCrae, and S.C. Remick Cancer Res. 62 2002 3408 3416
10. G.R. Pettit, M.R. Rhodes, D.L. Herald, D.J. Chaplin, M.R.L. Stratford, E. Hamel, R.K. Pettit, J.-C. Chapuis, and D. Oliva Anti-Cancer Drug Des. 13 1998 981 993
11. K. Ohsumi, T. Hatanaka, K. Fujita, R. Nakagawa, Y. Fukuda, Y. Nihei, Y. Suga, Y. Morinaga, Y. Akiyama, and T. Tsuji Bioorg. Med. Chem. Lett. 8 1998 3153 3158
12. S. Aprile, E. Del Grosso, G.C. Tron, and G. Grosa Drug Metab. Dispos. 35 2007 2252 2261
13. B.L. Flynn, G.S. Gill, D.W. Grobelny, J.H. Chaplin, D. Paul, A.F. Leske, T.C. Lavranos, D.K. Chalmers, S.A. Charman, E. Kostewicz, D.M. Shackleford, J. Morizzi, E. Hamel, M.K. Jung, and G. Kremmidiotis J. Med. Chem. 54 2011 6014 6027
14. N.H. Nam Curr. Med. Chem. 10 2003 1692 1722 (and references therein)
15. G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, and A.A. Genazzani J. Med. Chem. 49 2006 3033 3044 (and references therein)
16. M. Marelli, F. Conforti, G.A. Statti, X. Cachet, S. Michel, F. Tillequin, and F. Menichini Curr. Med. Chem. 18 2011 3035 3081 (and references therein)
17. A. Chaudhary, S.N. Pandeya, P. Kumar, P.P. Sharma, S. Gupta, N. Soni, K.K. Verma, and G. Bhardwaj Mini-Rev. Med. Chem. 7 2007 1186 1205 (and references therein)
18. A. Cirla, and J. Mann Nat. Prod. Rep. 20 2003 558 564 (and references therein)
19. M. Arthuis, R. Pontikis, G.G. Chabot, J. Seguin, L. Quentin, S. Bourg, L. Morin-Allory, and J.-C. Florent ChemMedChem 6 2011 1693 1705 (and references therein)
20. Y. Shan, J. Zhang, Z. Liu, M. Wang, and Y. Dong Curr. Med. Chem. 18 2011 523 538 (and references therein)
21. O. Provot, A. Giraud, J.-F. Peyrat, M. Alami, and J.-D. Brion Tetrahedron Lett. 46 2005 8547 8550
22. C. Mousset, A. Giraud, O. Provot, A. Hamze, J. Bignon, J.M. Liu, S. Thoret, J. Dubois, J.-D. Brion, and M. Alami Bioorg. Med. Chem. Lett. 18 2008 3266 3271
23. S. Messaoudi, A. Hamze, O. Provot, B. Tréguier, J. Rodrigo De Losada, J. Bignon, J.M. Liu, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, and M. Alami ChemMedChem 6 2011 488 497
24. C. Mousset, O. Provot, A. Hamze, J. Bignon, J.-D. Brion, and M. Alami Tetrahedron 64 2008 4287 4294
25. N. L'Hermite, A. Giraud, O. Provot, J.-F. Peyrat, M. Alami, and J.-D. Brion Tetrahedron 62 2006 1199 12002
26. E. Rasolofonjatovo, O. Provot, A. Hamze, J. Bignon, S. Thoret, J.-D. Brion, and M. Alami Eur. J. Med. Chem. 45 2010 3617 3626
27. A. Hamze, D. Veau, O. Provot, J.-D. Brion, and M. Alami J. Org. Chem. 74 2009 1337 1340
28. F. Liron, M. Gervais, J.-F. Peyrat, M. Alami, and J.-D. Brion Tetrahedron Lett. 44 2003 2789 2794
29. B. Tréguier, A. Hamze, O. Provot, J.-D. Brion, and M. Alami Tetrahedron Lett. 50 2009 6549 6552
30. S. Messaoudi, B. Tréguier, A. Hamze, O. Provot, J.-F. Peyrat, J. Rodrigo De Losada, J.M. Liu, J. Bignon, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, and M. Alami J. Med. Chem. 52 2009 4538 4542
31. A. Hamze, A. Giraud, S. Messaoudi, O. Provot, J.-F. Peyrat, J. Bignon, J.M. Liu, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, and M. Alami ChemMedChem 4 2009 1912 1924
32. A. Hamze, E. Rasolofonjatovo, O. Provot, C. Mousset, D. Veau, J. Rodrigo, J. Bignon, J.M. Liu, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, and M. Alami ChemMedChem 6 2011 2179 2191
33. M.A. Soussi, S. Aprile, S. Messaoudi, O. Provot, E. Del Grosso, J. Bignon, J. Dubois, J.-D. Brion, G. Grosa, and M. Alami ChemMedChem 6 2011 1781 1788
34. K.G. Pinney, V.P. Mocharla, Z. Chen, C.M. Garner, A. Ghatak, M. Hadimani, J. Kessler, J.M. Dorsey, K. Edvardsen, D.J. Chaplin, J. Prezioso, U.R. Ghatak, U.S. Patent Appl. Publ. 20040043969 A1, 2004.
35. K.G. Pinney, V.P. Mocharla, P. Vani, Z. Chen, C.M. Garner, A. Ghatak, M. Hadimani, J. Kessler, J.M. Dorsey PCT Int. Appl., WO 2001068654 A2 20010920, 2001.
36. E. Rasolofonjatovo, O. Provot, A. Hamze, J. Rodrigo, J. Bignon, J. Wdzieczak-Bakala, D. Desravines, J. Dubois, J.-D. Brion, and M. Alami Eur. J. Med. Chem. 52 2012 22 32
37. E. Rasolofonjatovo, B. Tréguier, O. Provot, A. Hamze, E. Morvan, J.-D. Brion, and M. Alami Tetrahedron Lett. 52 2011 1036 1040
38. E. Rasolofonjatovo, B. Tréguier, O. Provot, A. Hamze, J.-D. Brion, and M. Alami Eur. J. Org. Chem. 2012 1603 1615
39. M. Sriram, J.J. Hall, N.C. Grohmann, T.E. Strecker, T. Wootton, A. Franken, M.L. Trawick, and K.G. Pinney Bioorg. Med. Chem. 16 2008 8161 8171
40. K.G. Pinney, M. Sriram, U.S. PCT Appl., WO 2006138427 A2, 2006.
41. J. Barluenga, P. Moriel, C. Valdés, and F. Aznar Angew. Chem. Int. Ed. 46 2007 5587 5590
42. J. Barluenga, and C. Valdés Angew. Chem. Int. Ed. 50 2011 7486 7500
43. M. Alami, F. Liron, M. Gervais, J.-F. Peyrat, and J.-D. Brion Angew. Chem. Int. Ed. 41 2002 1578 1580
44. G.S. Gill, D.W. Grobelny, J.H. Chaplin, and B.L. Flynn J. Org. Chem. 73 2008 1131 1134
45. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467 4470
46. M. Alami, F. Ferri, and G. Linstrumelle Tetrahedron Lett. 34 1993 6403 6406
47. N. Olivi, E. Thomas, J.-F. Peyrat, M. Alami, and J.-D. Brion Synlett 2004 2175 2179
48. G. Le Bras, O. Provot, J.-F. Peyrat, M. Alami, and J.-D. Brion Tetrahedron Lett. 47 2006 5497 5501
49. M. Jacubert, O. Provot, J.-F. Peyrat, A. Hamze, J.-D. Brion, and M. Alami Tetrahedron 66 2010 3775 3787
50. M. Jacubert, A. Hamze, O. Provot, J.-F. Peyrat, J.-D. Brion, and M. Alami Tetrahedron Lett. 50 2009 3588 3592
51. G. Le Bras, A. Hamze, S. Messaoudi, O. Provot, P.-B. Le Calvez, J.-D. Brion, and M. Alami Synthesis 2008 1607 1611
52. E. Brachet, A. Hamze, J.-F. Peyrat, J.-D. Brion, and M. Alami Org. Lett. 12 2010 4042 4045
53. For the synthesis of 5-arylbenzoxepins according to Suzuki couplings, see Ref. [27] and I. Barrett, M.J. Meegan, R.B. Hughes, M. Carr, A.J.S. Knox, N. Artemenko, G. Golfis, D.M. Zisterer, and D.G. Lloyd Bioorg. Med. Chem. 16 2008 9554 9573
54. I. Barrett, M. Carr, N. O'Boyle, L.M. Greene, A.J.S. Knox, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan J. Enzyme Inhib. Med. Chem. 25 2010 180 194
55. M. Jacubert, A. Tikad, O. Provot, A. Hamze, J.-D. Brion, and M. Alami Eur. J. Org. Chem. 2010 4492 4500
56. A. Bekaert, O. Provot, O. Rasolojaona, M. Alami, and J.-D. Brion Tetrahedron Lett. 46 2005 4187 4191
57. During the preparation of this manuscript, a similar strategy for the synthesis of benzosuberene derivatives was reported, see: Z. Chen, C.J.O. 'Donnell, and A. Maderna Tetrahedron Lett. 53 2012 64 66
58. S. Messaoudi, J.-D. Brion, and M. Alami Adv. Synth. Catal. 352 2010 1677 1687
59. S. Messaoudi, J.-D. Brion, and M. Alami Mini-Rev. Org. Chem. 8 2011 448 454
60. J. Chen, Y. Zhang, L. Yang, X. Zhang, J. Liu, L. Li, and H. Zhang Tetrahedron 63 2007 4266 4270
61. K. Anderson, T. Ikawa, R.E. Tundel, and S.L. Buchwald J. Am. Chem. Soc. 128 2006 10694 10695
62. A. Giraud, O. Provot, A. Hamze, J.D. Brion, and M. Alami Tetrahedron Lett. 49 2008 1107 1110
63. K. Ohsumi, R. Nakagawa, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y. Nihei, K. Ohishi, Y. Suga, Y. Akiyama, and T. Tsuji J. Med. Chem. 41 1998 3022 3032
64. M. Cushman, D. Nagarathnam, D. Gopal, H.-M. He, C.M. Lin, and E. Hamel J. Med. Chem. 35 1992 2293 2314
65. Y.G. Tong, X.W. Zhang, M.Y. Geng, J.M. Yue, X.L. Xin, T. Fang, S. Xu, L.J. Tong, M.H. Li, C. Zhang, W.H. Li, L.P. Lin, and J. Ding Mol. Pharmacol. 69 2006 1226 1233
66. R.B. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, and M. Knossow Nature 428 2004 198 202
67. M. Rosillo, G. Dominguez, L. Casarrubios, U. Amador, and J. Pérez-Castells J. Org. Chem. 69 2004 2084 2093
68. A.R. Pereira, W.K. Strangman, F. Marion, L. Feldberg, D. Roll, R. Mallon, I. Hollander, and R.J. Anderson J. Med. Chem. 53 2010 8523 8533
69. M.L. Shelanski, F. Gaskin, and C.R. Cantor Proc. Natl. Acad. Sci. U.S.A. 70 1973 765 768
70. D.M. Barron, S.K. Chatterjee, R. Ravindra, R. Roof, E. Baloglu, D.G.I. Kingston, and S. Bane Anal. Biochem. 315 2003 49 56
71. C. Venot, M. Maratrat, C. Dureuil, E. Conseiller, L. Bracco, and L. Debussche EMBO J. 17 1998 4668 4679
72. D.A. Case, T.A. Darden, T.E. Cheatham III, C.L. Simmerling, J. Wang, R.E. Duke, R. Luo, K.M. Merz, B. Wang, D.A. Pearlman, M. Crowley, S. Brozell, V. Tsui, H. Gohlke, J. Mongan, V. Hornak, G. Cui, P. Beroza, C. Schafmeister, J.W. Caldwell, W.S. Ross, and P.A. Kollman AMBER8 2008 University of California San Francisco
73. M.L. Verdonk, J.C. Cole, M.J. Hartshorn, C.W. Murray, and R.D. Taylor Proteins 52 2003 609 623