Synthesis and characterization of new organometallic benzo[b]thiophene derivatives with potential antitumor properties

Organometallics

Volumn 28, Issue 18, 2009, Pages 5412-5423

  Ferreira, André P ^a   Ferreira Da Silva, João L ^a   Duarte, M Teresa ^a   Fatima Minas Da Piedade M ^a,b   Paula Robalo, M ^b,c   Harjivan, Shrika G ^a   Marzano, Cristina ^d   Gandin, Valentina ^d   Matilde Marques, M ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b UNIVERSITY OF LISBON   (Portugal)

^c INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

^d UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CELL CULTURE; CELL DEATH; CYCLIC VOLTAMMETRY; CYTOTOXICITY; DIAGNOSIS; DRUG INTERACTIONS; ORGANOMETALLICS; X RAY DIFFRACTION;

BENZOYL SUBSTITUENTS; CASPASE-3 ACTIVATION; HUMAN TUMOR CELL LINES; ORGANOMETALLIC MOIETY; SELECTIVE ESTROGEN RECEPTOR MODULATORS; SYNTHESIS AND CHARACTERIZATIONS; THERAPEUTIC PROPERTIES; THIOPHENE DERIVATIVES;

THIOPHENE;

EID: 70349326103     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9003835     Document Type: Article

References (72)

1. (a) Jaouen, G.; vessieres, A.; Butler, I. S. Acc. Chem. Res. 1993 26, 361.
2. (b) Fish, R. H.; Jaouen, G. Organometallics 2003, 22, 2166.
3. (c) Metzler-Nolte, N. Angew. Chem., Int. Ed. 2001, 40, 1040.
4. Allardyce, C. S.; Dorcier, A.; Scolaro, C.; Dyson, P. J. Appl. Organomet. Chem. 2005, 19, 1.
5. (a) Dive, D.; Biot, C. ChemMedChem 2008, 3, 383.
6. (b) Kreidenweiss, A.; Kremsner, P. G.; Dietz, K.; Mordmüller, B. Am. J. Trop. Med. Hyg. 2006, 75, 1178.
7. (a) Rosenberg, B.; VanCamp, L.; Trosko, J. E.; Mansour, V. H. Nature 1969, 222, 385.
8. (b) Rosenberg, B.; VanCamp, L. Cancer Res. 1970, 30, 1799.
9. (c) Kociba, R. J.; Sleight, S. D.; Rosenberg, B. Cancer Chemother. Rep. 1970, 54, 325.
10. Wong, E.; Giandomenico, C. M. Chem. Rev. 1999, 99, 2451.
11. (a) Kelland, L. R.; Sharp, S. Y.; O'Neill, C. F.; Raynaud, F. I.; Beale,P. J.; Judson, I. R. J. Inorg. Biochem. 1999, 77, 111.
12. (b)Perez, J. M.; Fuertes, M. A.; Alonso, C.; Navarro-Ranninger, C. Crit. Rev. Oncol. Hematol. 2000, 35, 109.
13. (c) Ho, Y.-P.; Au-Yeung, S. C. F.; To, K. K. W Med. Res. Rev. 2003, 23, 633.
14. (d) Wang, D.; Lippard, S. J. Nat. Rev. Drug Discovery 2005, 4, 307-320.
15. (a) Clarke, M. J.; Zhu, F.; Frasca, D. R. Chem. Rev. 1999, 99, 2511.
16. (b) Auzias, M.; Therrien, B.; Süss-Fink, G.; Ště pnička, P.; Ang, W. H.; Dyson, P. J. Inorg. Chem. 2008, 47, 578.
17. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931.
18. Jaouen, G., Ed. Bioorganometallics. Biomolecules, Labeling, Medicine; Wiley-VCH: Weinheim, Germany, 2006.
19. Jaouen, G.; Top, S.; Vessières, A.; Leclercq, G.; McGlinchey, M. J. Curr. Med. Chem. 2004, 11, 2505.
20. Top, S.; Vessières, A.; Leclercq, G.; Quivy, J.; Tang, J; Vaissermann, J.; Huche, M.; Jaouen, G. Chem.-Eur. J. 2003, 9, 5223.
21. (a) Early Breast Cancer Trialists' Collaborative Group (EBTCG). Lancet 1998, 351, 1451.
22. (b) Early Breast Cancer Trialists' Collaborative Group (EBTCG). Lancet 2005, 365, 1687.
23. (a) Cuzick, J.; Powles, T.; Veronesi, U.; Forbes, J.; Edwards, R.; Ashley, S.; Boyle, P. Lancet 2003, 361, 296.
24. (b) Fisher, B.; Costantino, J. P.; Wickerham, D. L.; Cecchini, R. S.; Cronin, W. M.; Robidoux, A.; Bevers, T. B.; Kavanah, M. T.; Atkins, J. N.; Margolese, R. G.; Runowicz, C. D.; James, J. M.; Ford, L. G.; Wolmark, N. J. Natl. Cancer Inst. 2005, 97, 1652.
25. (c) Cuzick, J.; Forbes, J. F.; Sestak, I.; Cawthom, S.; Hamed, H.; Holli, K.; Howell, A. for the International Breast Cancer Intervention Study (IBIS) I Investigators. J. Natl. Cancer Inst. 2007, 99, 272.
26. (d) Powles, T. J.; Ashley, S.; Tidy, A.; Smith, I. E.; Dowsett, M. J. Natl. Cancer Inst. 2007, 99, 283.
27. (a) Braithwaite, R. S.; Chlebowski, R. T.; Lau, J.; George, S.; Hess, R.; Col, N. F. J. Gen. Intern. Med. 2003, 18, 937.
28. (b) Swerdlow, A. J.; Jones, M. E. for the British Tamoxifen Second Cancer Study Group. J. Natl. Cancer Inst. 2005, 97, 375.
29. (c) Bland, A. E.; Calingaert, B.; Alvarez Secord, A.; Lee, P. S.; Valea, F. A.; Berchuck, A.; Soper, J. T.; Havrilesky, L. Gynecol. Oncol. 2009, 112, 150.
30. (a) Gottardis, M. M.; Jordan, V. C. Cancer Res. 1987, 47, 4020.
31. (b) Delmas, P. D.; Bjamason, N. H.; Mitlak, B. H.; Ravoux, A.-C; Shah, A. S.; Huster, W. J.; Draper, M.; Christiansen, C. N. Engl. J. Med. 1997, 337, 1641.
32. (c) Johnston, C. C. Jr; Bjamason, N. H.; Cohen, F. J.; Shah, A.; Lindsay, R.; Mitlak, B. H.; Huster, W; Draper, M. W.; Harper, K. D.; Heath, H. Ill; Gennari, C.; Christiansen, C.; Arnaud, C. D.; Delmas, P. D. Arch. Intern. Med. 2000, 160, 3444.
33. (d) Cohen, F. J.; Watts, S.; Shah, A.; Akers, R.; Plouffe, L. Jr. Obstet. Gynecol. 2000, 95, 104.
34. (a) Cummings, S. R.; Eckert, S.; Krueger, K. A.; Grady, D.; Powles, T. J.; Cauley, J. A.; Norton, L.; Nickelsen, T.; Bjamason, N. H.; Morrow, M.; Lippman, M. E.; Black, D.; Glusman, J. E.; Costa, A.; Jordan, V. C. J. Am. Med. Assoc. 1999, 281, 2189.
35. (b) Vogel, V. G.; Costantino, J. P.; Wickerham, D. L.; Cronin, W. M.; Cecchini, R. S.; Atkins, J. N.; Bevers, T. B.; Fehrenbacher, L.; Pajon, E. R. Jr.; Wade, J. L. III; Robidoux, A.; Margolese, R. G.; James, J.; Lippman, S. M.; Runowicz, C. D.; Ganz, P. A.; Reis, S. E.; McCaskill-Stevens, W; Ford, L. G.; Jordan, V. C.; Wolmark, N. for the National Surgical Adjuvant Breast and Bowel Project (NSABP). J. Am. Med. Assoc. 2006, 295, 2727.
36. (c) Land, S. R.; Wickerham, D. L.; Costantino, J. P.; Ritter, M. W.; Vogel, V. G.; Lee, M.; Pajon, E. R.; Wade, J. L. Ill; Dakhil, S.; Lockhart, J. B. Jr; Wolmark, N.; Ganz, P. A. J. Am. Med. Assoc 2006, 295, 2742.
37. (d) Barrett-Connor, E.; Mosca, L.; Collins, P.; Geiger, M. J.; Grady, D.; Komitzer, M.; McNabb, M. A.; Wenger, N. K. for the Raloxifene Use for The Heart (RUTH) trial investigators. N. Engl. J. Med. 2006, 355, 125.
38. Dayan, G.; Lupien, M.; Auger, A.; Anghel, S. I.; Rocha, W.; Croisetière, S.; Katzenellenbogen, J. A.; Mader, S. Mol. Pharmacol. 2006, 70, 579.
39. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, U.K., 1988.
40. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
41. Fang, J.-X.; Jin, Z.; Li, Z.-M.; Liu, W. Appl. Organomet. Chem. 2003, 17, 145.
42. Schlögl, L.; Egger, M. Monatsh. Chem. 1962, 95, 316.
43. SMART and SAINT, Area Detector Control and Integration Software; Bruker AXS: Madison, WI, 2004.
44. : Sheldrick G. M., SADABS, Program for Empirical Absorption Correction of Area Detectors (Version 2.10); University of Göttingen: Göttingen, Germany, 2004.
45. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
46. Sheldrick, G. M. SHELXL-97, a Computer Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
47. Farrugia, L. J. WmGX (vi.64.03b). J. Appl. Crystallogr. 1999, 32, 837.
48. Farrugia, L. J. ORTEP-3 for Windows (vl.076), based on ORTEP-III (vl.03) by: Johnson, C. K.; Burnett, M. N. J. Appl. Crystallogr. 1997, 30, 565.
49. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; MacRae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. 2002, B58, 389.
50. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589.
51. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1-S83.
52. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
53. (a) Köpf-Maier, P. Z. Naturforsch. C 1985, 40, 843.
54. (b) Neuse, E. W; Kanzawa, F. Appl. Organomet. Chem. 1990, 4, 19.
55. (c) Osella, D.; Ferrali, M.; Zanello, P.; Laschi, F.; Fontani, M.; Nervi, C.; Cavigiolio, G. Inorg. Chim. Acta 2000, 306, 42.
56. (d) Tabbì, G.; Cassino, C.; Cavigiolio, G.; Colangelo, D.; Ghiglia, A.; Viano, I.; Osella, D. J. Med. Chem. 2002, 45, 5786.
57. (a) Hillard, E.; Vessières, A.; Thouin, L.; Jaouen, G.; Amatore, C. Angew. Chem., Int. Ed. 2006, 45, 285.
58. (b) Hillard, E.; Vessières, A.; Le Bideau, F.; Plazuk, D.; Spera, D.; Huché, M.; Jaouen, G. ChemMedChem 2006, 1, 551.
59. (c) Hillard, E. A.; Pigeon, P.; Vessières, A.; Amatore, C.; Jaouen, G. Dalton Trans. 2007, 5073.
60. (a) Bjerrum, J.; Schwarzenbach, G.; Sillen, L. G. Stability Constants; The Chemical Society: London, U.K., 1958.
61. (b) Hall, H. K. Jr. J. Am. Chem. Soc. 1957, 79, 5441.
62. Maurice, C.; Schöllhorn, B.; Canet, I.; Mousset, G.; Mousty, C.; Guilbot, J.; Plusquellec, D. Eur. J. Org. Chem. 2000, 813.
63. Garcia, M. H.; Florindo, P.; Piedade, M. F. M.; Duarte, M. T.; Robalo, M. P.; Heck, J.; Wittenburg, C.; Holtmann, J.; Licandro, E. J. Organomet. Chem. 2008, 693, 2987.
64. (a) Shono, T.; Toda, T.; Oshino, N. J. Am. Chem. Soc. 1982, 104, 2639.
65. (b) Jurva, U.; Bissel, P.; Isin, E. M.; Igarashi, K; Kuttab, S.; Castagnoli, N. Jr. J. Am. Chem. Soc. 2005, 127, 12368.
66. Chen, G. G.; Zeng, Q.; Tse, G. M. K. Med. Res. Rev. 2008, 28, 954.
67. Marzano, C.; Gandin, V.; Folda, A.; Scutari, G.; Bindoli, A.; Rigobello, M. P. Free Radical Biol. Med. 2007, 42, 872.
68. (a) Zinkewich-Péotti, K.; Andrews, P. A. Cancer Res. 1992, 52, 1902.
69. (b) Gandin, V.; Fernandes, A. P.; Rigobello, M. P.; Dani, B.; Sorrentino, F.; Tisato, F.; Bjömstedt, M.; Bindoli, A.; Sturaro, A.; Relia, R.; Marzano C. Biochem. Pharmacol. 2009, doi: 10.1016/j.bcp.2009.07.023, in press.
70. Kuo, M. T. Adv. Exp. Med. Biol. 2007, 608, 23.
71. Siddik, Z. H. Oncogene 2003, 22, 7265.
72. Mukherjee, S.; Nagar, S.; Mullick, S.; Mukherjee, A.; Saha, A. J. Mol. Graph. Model. 2008, 26, 884.