Synthesis and biological evaluation of enantiomerically pure cyclopropyl analogues of combretastatin A4

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 5, 2013, Pages 1357-1366

  Ty, Nancy ^a,b   Pontikis, Renée ^a,b   Chabot, Guy G ^c,d   Devillers, Emmanuelle ^a,b   Quentin, Lionel ^c,d   Bourg, Stéphane ^e,f   Florent, Jean Claude ^a,b  

^a INSTITUT CURIE   (France)

^b CNRS   (France)

^c UNIVERSITÉ PARIS DESCARTES   (France)

^d Centre National de la Recherche Scientifique   (France)

^e UNIVERSITÉ D'ORLÉANS   (France)

^f CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

Author keywords

Combretastatin; Cyclopropyl compounds; Palladium catalyzed reactions; Tubulin; Vascular disrupting agents

Indexed keywords

2 (3 AMINO 4 METHOXYPHENYL) 1 (3',4',5' TRIMETHOXYPHENYL)CYCLOPROPANE; 2 (3 TERT BUTYLDIMETHYLSILYLOXY 4 METHOXYPHENYL) 1 (3',4',5' TRIMETHOXYPHENYL)CYCLOPROPANE; 2 (4 METHOXY 3 HYDROXYPHENYL) 1 (3',4',5' TRIMETHOXYPHENYL)CYCLOPROPANE; 2 (4 METHOXY 3 NITROPHENYL) 1 (3',4',5' TRIMETHOXYPHENYL)CYCLOPROPANE; 2 (4 METHOXYPHENYL) 1 (3',4',5' TRIMETHOXYPHENYL)CYCLOPROPANE; 4,4,5,5 TETRAMETHYL 2 [2 (3,4,5 TRIMETHOXYPHENYL)CYCLOPROPYL] [1,3,2] DIOXABOROLANE; 4,4,5,5 TETRAMETHYL 2 [2 (3,4,5 TRIMETHOXYPHENYL)ETHENYL] [1,3,2] DIOXABOROLANE; 4,5 BIS[METHOXYDIPHENYLMETHYL 2 [2 (3',4',5' TRIMETHOXYPHENYL)CYCLOPROPYL]] [1,3,2] DIOXABOROLANE; 4,5 BIS[METHOXYDIPHENYLMETHYL 2 [2 (3,4,5 TRIMETHOXYPHENYL)ETHENYL]] [1,3,2] DIOXABOROLANE; 5 BROMO 1 METHOXYANILINE; [2 (3',4',5' TRIMETHOXYPHENYL)CYCLOPROPYL] TRIFLUOROBORATE DE POTASSIUM; BORON DERIVATIVE; CIS 2 (2 STYRYL) 1 (3,4,5 TRIMETHOXYPHENYL)CYCLOPROPANE; COLCHICINE; COMBRETASTATIN A4; CYCLOPROPANE DERIVATIVE; HALIDE; TUBULIN; UNCLASSIFIED DRUG; VASCULAR TARGETING AGENT;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIVASCULAR ACTIVITY; ARTICLE; BINDING SITE; CHIRALITY; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLOPROPANATION; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; MELANOMA CELL; MICROTUBULE ASSEMBLY; MOLECULAR DOCKING; MOUSE; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ANIMALS; BINDING SITES; CELL LINE, TUMOR; CELL SURVIVAL; COLCHICINE; CYCLOPROPANES; DRUG EVALUATION, PRECLINICAL; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; MICE; MOLECULAR DOCKING SIMULATION; STEREOISOMERISM; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS;

EID: 84873737093     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.056     Document Type: Article

References (93)

1. J.N. Folkman Engl. J. Med. 285 1971 1182
2. J. Denekamp Br. J. Radiol. 60 1993 181
3. V.L. Heath, and R. Bicknell Nat. Rev. Clin. Oncol. 6 2009 395
4. G.M. Tozer, C. Kanthou, and B.C. Baguley Nat. Rev. Cancer 5 2005 423
5. C. Kanthou, and G.M. Tozer Int. J. Exp. Pathol. 90 2009 284
6. D.W. Siemann Cancer Treat. Rev. 37 2011 63 and references cited therein
7. For reviews on VDAs, see: P. Hinnen, and F.A.L.M. Eskens Br. J. Cancer 96 2007 1159
8. J.W. Lippert III Bioorg. Med. Chem. 15 2007 605
9. S.X. Cai Recent Patents Anticancer Drug Disc. 2 2007 79
10. E.L. Schwartz Clin. Cancer Res. 15 2009 2594
11. M.J. McKeage, and B.C. Baguley Cancer 116 2010 1859
12. L.G.M. Daenen, J.M.L. Roodhart, Y. Shaked, and E.E. Voest Curr. Clin. Pharm. 5 2010 178
13. For reviews on CA4, see: C.M.L. West, and P. Price Anti-Cancer Drugs 15 2004 179
14. D.W. Siemann, D.J. Chaplin, and P.A. Walicke Expert Opin. Investig. Drugs 18 2009 189
15. C.J. Mooney, G. Nagaiah, P. Fu, J.K. Wasman, M.M. Cooney, P.S. Savvides, J.A. Bokar, A. Dowlati, D. Wang, S.S. Agarwala, S.M. Flick, P.H. Hartman, J.D. Ortiz, P.N. Lavertu, and S.C. Remick Thyroid 19 2009 233
16. G.J. Rustin, G. Shreeves, P.D. Nathan, A. Gaya, T.S. Ganesan, D. Wang, J. Boxall, L. Poupard, D.J. Chaplin, M.R.L. Stratford, J. Balkissoon, and M. Zweifel Br. J. Cancer 102 2010 1355
17. http://clinicaltrials.gov/ct2/home, june 2012.
18. A. Delmonte, and C. Sessa Expert Opin. Invest. Drugs 18 2009 1541
19. Tresca, P.; Tosi, D.; van Doorn, L.; Fontaine, H.; Gaast, A. V.; Veyrat-Follet, C.; Oprea, C.; Dieras, V.; Eskens, F. J. Clin. Oncol., ASCO Meeting Abstracts, 2010, 28, abstract 3023.
20. Ura, T.; Takahashi, S.; Yokota, T.; Shitara, K.; Muro, K.; Nakano, K.; Chin, K.; Yokoyama, M.; Hatake, K.; Aoyama, T. Abstract of Papers, AACR, Mol. Cancer Ther. 2011, 10, abstract B54.
21. L. Vincent, P. Kermani, L.M. Young, J. Cheng, F. Zhang, K. Shido, G. Lam, H. Bompais-Vincent, Z. Zhu, D.J. Hicklin, P. Bohlen, D.J. Chaplin, C. May, and S. Rafii J. Clin. Invest. 115 2005 2992
22. C. Kanthou, and G.M. Tozer Blood 99 2002 2060
23. G.G. Dark, S.A. Hill, V.E. Prise, G.M. Tozer, G.R. Petitt, and D.J. Chaplin Cancer Res. 57 1997 1829
24. M.R. Horsmann, and D.W. Siemann Cancer Res. 66 2006 11520
25. For reviews on CA4 analogues, see: N.-H. Nam Curr. Med. Chem. 10 2003 1697
26. H.P. Hsieh, J.P. Liou, and N. Mahindroo Curr. Pharm. Design 11 2005 1655
27. G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, and A.A. Genazzani J. Med. Chem. 49 2006 3033
28. T. Brown, H. Holt Jr., and M. Lee Top. Heterocycl. Chem. 2 2006 1
29. R. Singh, and H. Kaur Synthesis 15 2009 2471
30. Y. Shan, J. Zhang, Z. Liu, M. Wang, and Y. Dong Curr. Med. Chem. 18 2011 523
31. M. Marelli, F. Conforti, G.A. Statti, X. Cachet, S. Michel, F. Tillequin, and F. Menichini Curr. Med. Chem. 18 2011 3055
32. For recent reports on heterocyclic CA4 derivatives, see: N.M. O'Boyle, L.M. Greene, O. Bergin, J.-B. Fichet, T. McCabe, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan Bioorg. Med. Chem. 19 2011 2306
33. M. Lee, O. Brockway, A. Dandavati, S. Tzou, R. Sjoholm, V. Satam, C. Westbrook, S.L. Mooberry, M. Zeller, B. Babu, and M. Lee Eur. J. Med. Chem. 2011 3099
34. R. Romagnoli, P.G. Baraldi, A. Brancale, A. Ricci, E. Hamel, R. Bortolozzi, G. Basso, and G. Viola J. Med. Chem. 54 2011 5144
35. B. Biersack, Y. Muthukumar, R. Schobert, and F. Sasse Bioorg. Med. Chem. Lett. 21 2011 6270
36. R. Fürst, I. Zupkó, A.G. Berényi, G.F. Ecker, and U. Rinner Bioorg. Med. Chem. Lett. 19 2009 6948
37. J. Kaffy, R. Pontikis, D. Carrez, A. Croisy, C. Monneret, and J.-C. Florent Bioorg. Med. Chem. 14 2006 4067
38. N. Ty, J. Kaffy, A. Arrault, S. Thoret, R. Pontikis, J. Dubois, L. Morin-Allory, and J.-C. Florent Bioorg. Med. Chem. Lett. 19 2009 1318
39. For selected reviews see: W.A. Donaldson Tetrahedron 57 2001 8589
40. H. Lebel, J.-F. Marcoux, C. Molinaro, and A.B. Charette Chem. Rev. 103 2003 977
41. J. Pietruszka Chem. Rev. 103 2003 1051
42. H. Pellissier Tetrahedron 64 2008 7041
43. P. Tang, and Y. Qin Synthesis 44 2012 2969
44. A.B. Charrette, and H. Juteau J. Am. Chem. Soc. 116 1994 2651
45. J.E.A. Luithle, and J. Pietruszka J. Org. Chem. 64 1999 8287
46. J.E.A. Luithle, and J. Pietruszka Eur. J. Org. Chem. 2000 2557
47. J. Pietruszka, and A. Witt J. Chem. Soc., Perkin Trans. 1 2000 4293
48. Others diols were used as chiral auxiliaries in the cyclopropanation of alkenylboronic esters; see, for example: T. Imai, H. Mineta, and S. Nishida J. Org. Chem. 55 1990 4986
49. J. Pietruszka, and M. Widenmeyer Synlett 1997 977
50. J. Pietruszka, and A. Witt Synlett 2003 91
51. H.A. Dieck, and R.F. Heck J. Org. Chem 1975 1083
52. H.C. Brown, and T.E. Cole Organometallics 2 1983 1316
53. H.-G. Herz, M.J. Queiroz, and G. Maas Synthesis 6 1999 1013
54. N.-W. Tseng, J. Mancuso, and M. Lautens J. Am. Chem. Soc. 128 2006 5338
55. J. Furukawa, N. Kawabata, and J. Nishimura Tetrahedron Lett. 28 1966 3353
56. P. Fontani, B. Carboni, M. Vaultier, and R. Carrié Tetrahedron Lett. 30 1989 4815
57. E. Hohn, J. Pietruszka, and G. Solduga Synlett 2006 1531
58. S. Darses, G. Michaud, and J.-P. Genêt Eur. J. Org. Chem. 1999 1875
59. G.-H. Fang, Z.J. Yan, and M.Z. Deng Org. Lett. 6 2004 357
60. A.B. Charette, S. Mathieu, and J.-F. Fournier Synlett 11 2005 1779 1782
61. G.A. Molander, and P.E. Gormisky J. Org. Chem. 73 2008 7481
62. A. Fürstner, and K. Nikolakis Liebigs Ann. 1996 2107
63. T. Oberhauser J. Org. Chem. 62 1997 4504
64. C. Heusèle, D. Bonne, and M.-F. Carlier Eur. J. Biochem. 165 1987 613
65. D.M. Barron, S.K. Chatterjee, R. Ravindra, R. Roof, E. Baloglu, D.G. Kingston, and S. Bane Anal. Biochem. 315 2003 49
66. K. Grosios, S.E. Holwell, A.T. McGown, G.R. Pettit, and M.C. Bibby Br. J. Cancer 81 1999 1318
67. S.M. Galbraith, D.J. Chaplin, F. Lee, M.R. Stratford, R.J. Locke, B. Vojnovic, and G.M. Tozer Anticancer Res. 21 2001 93
68. A. Cirla, and J. Mann Nat. Prod. Rep. 20 2003 558
69. M.B. Hadimani, J. Hua, M.D. Jonklaas, R.J. Kessler, Y. Sheng, A. Olivares, R.P. Tanpure, A. Weiser, J. Zhang, K. Edvardsen, R.R. Kane, and K.G. Pinney Bioorg. Med. Chem. Lett. 13 2003 1505
70. L.A. Wessjohann, W. Brandt, and T. Thiemann Chem. Rev. 103 2003 1625 1647
71. R.B. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, and M. Knossow Nature 428 2004 198
72. T.L. Nguyen, C. McGrath, A.R. Hermone, J.C. Burnett, D.W. Zaharevitz, B.W. Day, P. Wipf, E. Hamel, and R. Gussio J. Med. Chem. 48 2005 6107
73. A. Massaroti, A. Coluccia, R. Silvestri, G. Sorba, and A. Brancale ChemMedChem 7 2012 33
74. G. Jones, P. Willett, and R.C. Glen J. Mol. Biol. 245 1995 43 53
75. M. Arthuis, R. Pontikis, G.G. Chabot, J. Seguin, L. Quentin, S. Bourg, L. Morin-Allory, and J.-C. Florent ChemMedChem 6 2011 1693
76. N.M. Blanch, G.G. Chabot, L. Quentin, D. Scherman, S. Bourg, and D. Dauzonne Eur. J. Med. Chem. 54 2012 22
77. Y. Kong, J. Grembecka, M.C. Edler, E. Hamel, S.L. Mooberry, M. Sabat, J. Rieger, and M.L. Brown Chem. Biol. 12 2005 1007
78. C. Rappl, P. Barbier, V. Bourgarel-Rey, C. Grégoire, R. Gilli, M. Carre, S. Combes, J.-P. Finet, and V. Peyrot Biochemistry 45 2006 9210
79. S. Ducki, G. Mackenzie, B. Greedy, S. Armitage, J. Fournier Dit Chabert, E. Bennett, J. Nettles, J.P. Snyder, and N.J. Lawrence Bioorg. Med. Chem. 17 2009 7711
80. F. Arndt Org. Synth. Coll. 2 1943 165 167
81. K. Gaukroger, J.A. Hadfield, L.A. Hepworth, N.J. Lawrence, and A.T. McGown J. Org. Chem. 66 2001 8135
82. H.Y. Choi, and D.Y. Chi J. Am. Chem. Soc. 123 2001 9202 9203
83. D. Bonne, C. Heusele, C. Simon, and D. Pantaloni J. Biol. Chem. 260 1985 2819
84. S.L. Bane, R. Ravindra, and A.A. Zaydman J. Zhou, Microtubule Protocols 2007 Humana Press Totowa 281 288
85. C.J. Edgell, C.C. McDonald, and J.B. Graham Proc. Natl. Acad. Sci. U.S.A. 80 1983 3734
86. D. Bouis, G.A. Hospers, C. Meijer, G. Molena, and N.H. Mulder Angiogenesis 4 2001 91
87. D.A. Scudiero, R.H. Shoemaker, K.D. Paull, A. Monks, S. Tierney, T.H. Nofziger, M.J. Currens, D. Seniff, and M.R. Boyd Cancer Res. 48 1988 4827
88. Marvin 5.8.0, 2012, http://www.chemaxon.com.
89. From atoms and bonds to three-dimensional atomic coordinates: automatic model builders; J. Sadowski, and J. Gasteiger Chem. Rev. 93 1993 2567
90. (b) CORINA Fast Generation of High-Quality 3D Molecular Models: http://www.molecular-networks.com/products/corina.
91. Schrödinger Suite, version 2011 update 1, Schrödinger, Inc., New York, 2012.
92. Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides G.A. Kaminski, R.A. Friesner, J. Tirado-Rives, and W. Jorgensen J. Phys. Chem. B 105 2001 6474
93. P.J. Goodford J. Med. Chem. 28 1985 849