Simplified silvestrol analogues with potent cytotoxic activity

ChemMedChem

Volumn 9, Issue 7, 2014, Pages 1556-1566

  Hawkins, Bill C ^a,b   Lindqvist, Lisa M ^a,b   Nhu, Duong ^a,b   Sharp, Phillip P ^a,b   Segal, David ^a,b   Powell, Andrew K ^c   Campbell, Michael ^c   Ryan, Eileen ^c   Chambers, Jennifer M ^d   White, Jonathan M ^d   Rizzacasa, Mark A ^d   Lessene, Guillaume ^a,b   Huang, David C S ^a,b   Burns, Christopher J ^a,b,d  

^a WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c MONASH UNIVERSITY   (Australia)

^d UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

biological activity; drug discovery; silvestrol; structure activity relationships; translation inhibitors

Indexed keywords

3 HYDROXY 5 METHOXY 7 (4 METHOXYBENZYLOXY) 2 (4 METHOXYPHENYL) 4H CHROMEN 4 ONE; CYTOTOXIC AGENT; DEAD BOX PROTEIN; INITIATION FACTOR 4A; NATURAL PRODUCT; RAC 1,8B DIHYDROXY N,8 DIMETHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 6 (PYRIMIDIN 2 YLMETHOXY) 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 2 CARBOXAMIDE; RAC 8 METHOXY 6 [(4 METHOXYBENZYL)OXY] 3,3A DIPHENYL 1,2,3,3A TETRAHYDRO 8BH CYCLOPENTA[B]BENZOFURAN 1,8B DIOL; RAC 8 METHOXY 6 [(4 METHOXYBENZYL)OXY] 3,3A DIPHENYL 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 1 ONE; RAC METHYL 1 8B DIHYDROXY 8 METHOXY 8 METHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 6 (PYRIMIDIN 2 YLMETHOXY) 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 2 CARBOXYLATE; RAC METHYL 1,6 DIHYDROXY 8,8B DIMETHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAM 2 CARBOXYLATE; RAC METHYL 1,8B DIHYDROXY 6 [(4 ISOPROPYLBENZYL)OXY] 8 METHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 2 CARBOXYLATE; RAC METHYL 1,8B DIHYDROXY 8 METHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 6 (PYRIDIN 3 YLMETHOXY) 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 2 CARBOXYLATE; RAC METHYL 1,8B DIHYDROXY 8 METHOXY 6 [(2 METHOXYBENZYL)OXY] 3A (4 METHOXYPHENYL) 3 PHENYL 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAM 2 CARBOXYLATE; RAC METHYL 1,8B DIHYDROXY 8 METHOXY 6 [(3 METHOXYBENZYL)OXY] 3A (4 METHOXYPHENYL) 3 PHENYL 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAM 2 CARBOXYLATE; RAC METHYL 6 [(3 FLUOROBENZYL)OXY] 1,8B DIHYDROXY 8 METHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 2 CARBOXYLATE; RAC METHYL 6 [(4 BROMOBENZOYL)OXY] 1 HYDROXY 8,8B DIMETHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 2 CARBOXYLATEL; RAC METHYL 8B ETHOXY 1 HYDROXY 8 METHOXY 3A (4 METHOXYPHENYL) 3 PHENYL 6 (PYRIDIN 4 YLMETHOXY) 2,3,3A,8B TETRAHYDRO 1H CYCLOPENTA[B]BENZOFURAN 2 CARBOXYLATE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; EPISILVESTROL; PROTEIN BINDING; SILVESTROL; TRITERPENE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; ARTIFICIAL MEMBRANE; CANCER CELL; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG DETERMINATION; DRUG HALF LIFE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; LIVER MICROSOME; MEMBRANE PERMEABILITY; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN SYNTHESIS; PROTEIN SYNTHESIS INHIBITION; RETICULOCYTE LYSATE; STRUCTURE ACTIVITY RELATION; TRANSLATION INITIATION; X RAY CRYSTALLOGRAPHY; CELL SURVIVAL; CHEMISTRY; CONFORMATION; DRUG EFFECTS; METABOLISM; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; EUKARYOTIC INITIATION FACTOR-4A; HUMANS; MICROSOMES, LIVER; MOLECULAR CONFORMATION; PROTEIN BINDING; TRITERPENES;

EID: 84903817614     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201400024     Document Type: Article

References (52)

1. S. Ebada, N. Lajkiewicz, J. A. Porco, M. Li-Weber, P. Proksch, in Progress in the Chemistry of Organic Natural Products, Vol. 94 (Eds.:, A. D. Kinghorn, H. Falk, J. Kobayashi,), Springer, Wien, 2011, pp. 1-58.
2. S. Kim, A. A. Salim, S. M. Swanson, A. D. Kinghorn, Anti-Cancer Agents Med. Chem. 2006, 6, 319-345.
3. N. Ribeiro, F. Thuaud, C. Nebigil, L. Désaubry, Bioorg. Med. Chem. 2012, 20, 1857-1864.
4. G. A. Kraus, J. O. Sy, J. Org. Chem. 1989, 54, 77-83
5. B. M. Trost, P. D. Greenspan, B. V. Yang, M. G. Saulnier, J. Am. Chem. Soc. 1990, 112, 9022-9024
6. A. E. Davey, M. J. Schaeffer, R. J. K. Taylor, J. Chem. Soc. Perkin Trans. 1 1992, 2657-2666
7. M. R. Dobler, I. Bruce, F. Cederbaum, N. G. Cooke, L. J. Diorazio, R. G. Hall, E. Irving, Tetrahedron Lett. 2001, 42, 8281-8284
8. H. Li, B. Fu, M. A. Wang, N. Li, W. J. Liu, Z. Q. Xie, Y. Q. Ma, Z. Qin, Eur. J. Org. Chem. 2008, 1753-1758
9. J. A. Malona, K. Cariou, W. T. Spencer III, A. J. Frontier, J. Org. Chem. 2012, 77, 1891-1908.
10. B. Gerard, R. Cencic, J. Pelletier, J. A. Porco, Angew. Chem. 2007, 119, 7977-7980
11. Angew. Chem. Int. Ed. 2007, 46, 7831-7834
12. M. El Sous, M. L. Khoo, G. Holloway, D. Owen, P. J. Scammells, M. A. Rizzacasa, Angew. Chem. 2007, 119, 7981-7984
13. Angew. Chem. Int. Ed. 2007, 46, 7835-7838
14. T. E. Adams, M. El Sous, B. C. Hawkins, S. Hirner, G. Holloway, M. L. Khoo, D. J. Owen, G. P. Savage, P. J. Scammells, M. A. Rizzacasa, J. Am. Chem. Soc. 2009, 131, 1607-1616.
15. R. Cencic, M. Carrier, G. Galicia-Vazquez, M. E. Bordeleau, R. Sukarieh, A. Bourdeau, B. Brem, J. G. Teodoro, H. Greger, M. L. Tremblay, J. A. Porco, J. Pelletier, PLoS One 2009, 4, e 5223.
16. D. M. Lucas, R. B. Edwards, G. Lozanski, D. A. West, J. D. Shin, M. A. Vargo, M. E. Davis, D. M. Rozewski, A. J. Johnson, B.-N. Su, V. M. Goettl, N. A. Heerema, T. S. Lin, A. Lehman, X. Zhang, D. Jarjoura, D. J. Newman, J. C. Byrd, A. D. Kinghorn, M. R. Grever, Blood 2009, 113, 4656-4666.
17. S. Kim, B. Y. Hwang, B. N. Su, H. Chai, Q. Mi, A. D. Kinghorn, R. Wild, S. M. Swanson, Anticancer Res. 2007, 27, 2175-2183.
18. L. M. Lindqvist, I. Vikström, J. M. Chambers, K. McArthur, M. A. Anderson, K. J. Henley, L. Happo, L. Cluse, R. W. Johnstone, A. W. Roberts, B. T. Kile, B. A. Croker, C. J. Burns, M. A. Rizzacasa, A. Strasser, D. S. Huang, Cell Death Dis. 2012, 3, e 409.
19. Q. Mi, B.-N. Su, H. Chai, G. A. Cordell, N. R. Farnsworth, A. D. Kinghorn, S. M. Swanson, Anticancer Res. 2006, 26, 947-952.
20. P. Proksch, M. Giaisi, M. K. Treiber, K. Palfi, A. Merling, H. Spring, P. H. Krammer, M. Li-Weber, J. Immunol. 2005, 174, 7075-7084.
21. J. Y. Zhu, I. N. Lavrik, U. Mahlknecht, M. Giaisi, P. Proksch, P. H. Krammer, M. Li-Weber, Int. J. Cancer 2007, 121, 1839-1846.
22. G. Polier, J. Neumann, F. Thuaud, N. Ribeiro, C. Gelhaus, H. Schmidt, M. Giaisi, R. Kohler, W. W. Muller, P. Proksch, M. Leippe, O. Janssen, L. Desaubry, P. H. Krammer, M. Li-Weber, Chem. Biol. 2012, 19, 1093-1104.
23. M.-E. Bordeleau, F. Robert, B. Gerard, L. Lindqvist, S. M. H. Chen, H.-G. Wendel, B. Brem, H. Greger, S. W. Lowe, J. A. Porco, J. Pelletier, J. Clin. Invest. 2008, 118, 2651-2660.
24. P. Proksch, R. Edrada, R. Ebel, F. I. Bohnenstengel, B. W. Nugroho, Curr. Org. Chem. 2001, 5, 923-938.
25. B. Y. Hwang, B. N. Su, H. Chai, Q. Mi, L. B. Kardono, J. J. Afriastini, S. Riswan, B. D. Santarsiero, A. D. Mesecar, R. Wild, C. R. Fairchild, G. D. Vite, W. C. Rose, N. R. Farnsworth, G. A. Cordell, J. M. Pezzuto, S. M. Swanson, A. D. Kinghorn, J. Org. Chem. 2004, 69, 3350-3358.
26. L. Pan, L. B. Kardono, S. Riswan, H. Chai, E. J. C. de Blanco, C. M. Pannell, D. D. Soejarto, T. G. McCloud, D. J. Newman, A. D. Kinghorn, J. Nat. Prod. 2010, 73, 1873-1878.
27. J. M. Chambers, D. C. S. Huang, L. M. Lindqvist, G. P. Savage, J. M. White, M. A. Rizzacasa, J. Nat. Prod. 2012, 75, 1500-1504.
28. J. M. Chambers, L. M. Lindqvist, A. Webb, D. C. S. Huang, G. P. Savage, M. A. Rizzacasa, Org. Lett. 2013, 15, 1406-1409.
29. M. El Sous, M. A. Rizzacasa, Tetrahedron Lett. 2005, 46, 293-295.
30. A. Avdeef, Expert Opin. Drug Metab. Toxicol. 2005, 1, 325-342.
31. B. Gerard, G. Jones, J. A. Porco, J. Am. Chem. Soc. 2004, 126, 13620-13621.
32. M. Bennett, A. J. Burke, W. I. O'Sullivan, Tetrahedron 1996, 52, 7163-7178.
33. A. M. B. S. R. C. S. Costa, F. M. Dean, M. A. Jones, R. S. Varma, J. Chem. Soc. Perkin Trans. 1 1985, 799-808.
34. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560-3578.
35. B. Gerard, S. Sangji, D. J. O'Leary, J. A. Porco, J. Am. Chem. Soc. 2006, 128, 7754-7755.
36. F. Thuaud, N. Ribeiro, C. Gaiddon, T. Cresteil, L. Désaubry, J. Med. Chem. 2011, 54, 411-415.
37. F. Thuaud, Y. Bernard, G. Turkeri, R. Dirr, G. Aubert, T. Cresteil, A. Baguet, C. Tomasetto, Y. Svitkin, N. Sonenberg, C. G. Nebigil, L. Désaubry, J. Med. Chem. 2009, 52, 5176-5187.
38. S. P. Roche, R. Cencic, J. Pelletier, J. A. Porco, Angew. Chem. 2010, 122, 6683-6688
39. Angew. Chem. Int. Ed. 2010, 49, 6533-6538.
40. C. M. Rodrigo, R. Cencic, S. P. Roche, J. Pelletier, J. A. Porco, J. Med. Chem. 2012, 55, 558-562.
41. L. Lindqvist, M. Oberer, M. Reibarkh, R. Cencic, M. E. Bordeleau, E. Vogt, A. Marintchev, J. Tanaka, F. Fagotto, M. Altmann, G. Wagner, J. Pelletier, PLoS One 2008, 3, e 1583.
42. H. Sadlish, G. Galicia-Vazquez, C. G. Paris, T. Aust, B. Bhullar, L. Chang, S. B. Helliwell, D. Hoepfner, B. Knapp, R. Riedl, S. Roggo, S. Schuierer, C. Studer, J. A. Porco, J. Pelletier, N. R. Movva, ACS Chem. Biol. 2013, 8, 1519-1527.
43. T. Liu, S. J. Nair, A. Lescarbeau, J. Belani, S. Peluso, J. Conley, B. Tillotson, P. O'Hearn, S. Smith, K. Slocum, K. West, J. Helble, M. Douglas, A. Bahadoor, J. Ali, K. McGovern, C. Fritz, V. J. Palombella, A. Wylie, A. C. Castro, M. R. Tremblay, J. Med. Chem. 2012, 55, 8859-8878.
44. U. V. Saradhi, S. V. Gupta, M. Chiu, J. Wang, Y. Ling, Z. Liu, D. J. Newman, J. M. Covey, A. D. Kinghorn, G. Marcucci, D. M. Lucas, M. R. Grever, M. A. Phelps, K. K. Chan, AAPS J. 2011, 13, 347-356.
45. F. I. Bohnenstengel, K. G. Steube, C. Meyer, B. W. Nugroho, P. D. Hung, L. C. Kiet, P. Proksch, Z. Naturforsch. C 1999, 54, 55-60.
46. F. I. Bohnenstengel, K. G. Steube, C. Meyer, H. Quentmeier, B. W. Nugroho, P. Proksch, Z. Naturforsch. C 1999, 54, 1075-1083.
47. B. N. Su, H. Chai, Q. Mi, S. Riswan, L. B. Kardono, J. J. Afriastini, B. D. Santarsiero, A. D. Mesecar, N. R. Farnsworth, G. A. Cordell, S. M. Swanson, A. D. Kinghorn, Bioorg. Med. Chem. 2006, 14, 960-972.
48. A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518-1520.
49. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, A64, 112-122.
50. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
51. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.
52. D. Balan, C. J. Burns, N. G. Fisk, H. Hugel, D. C. Huang, D. Segal, C. White, J. Wagler, M. A. Rizzacasa, Org. Biomol. Chem. 2012, 10, 8147-8153.