The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugates

Journal of Organometallic Chemistry

Volumn 700, Issue , 2012, Pages 58-68

  Kowalski, Konrad ^a   Koceva Chyła, Aneta ^a   Pieniazek, Anna ^a   Bernasińska, Joanna ^a   Skiba, Joanna ^a   Rybarczyk Pirek, Agnieszka J ^a   Jóźwiak, Zofia ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Anticancer activity; Azaferrocene; Ferrocene; Michael addition; Thymine

Indexed keywords

ANTICANCER ACTIVITIES; AZAFERROCENE; FERROCENES; MICHAEL ADDITIONS; THYMINE;

ADDITION REACTIONS; CELL CULTURE; COMPUTATIONAL ELECTROMAGNETICS; CYCLIC VOLTAMMETRY; IRON COMPOUNDS; ORGANOMETALLICS; OXIDATION; SYNTHESIS (CHEMICAL);

CELLS;

EID: 84856227559     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.11.014     Document Type: Article

References (62)

1. H. Wamhoff, and J. Dzenis Adv. Heterocycl. Chem. 55 1992 129 259
2. M. Hocek Eur. J. Org. Chem. 2003 245 254
3. L. Meijer, and E. Raymond Acc. Chem. Res. 36 2003 417 425
4. E. De Clercq Biochem. Pharmacol. 42 1991 963 972
5. E. De Clerq Medical. Virol. 5 1995 149 164
6. E. De Clercq, A. Holy, I. Rosenberg, T. Sakuma, J. Balzarini, and P.C. Maudgal Nature 323 1986 464 467
7. L. Naesens, J. Balzarini, and E. De Clercq Rev. Med. Virol. 4 1997 147 159
8. E. De Clercq, T. Sakuma, M. Baba, R. Pauwels, J. Balzarini, I. Rosenberg, and A. Holy Antivir. Res. 8 1987 261 272
9. A.J. Wagstaff, D. Faulds, and K.L. Goa Drugs 47 1994 153 205
10. G. Darby J. Med. Virol. 1 1993 134 138
11. G. Jaouen Bioorganometallics: Biomolecules, Labeling, Medicine 2006 Wiley-VCH New York
12. D.R. van Stavern, and N. Metzler-Nolte Chem. Rev. 104 2004 5931 5985
13. N. Metzler-Nolte, and M. Salmain P. Štěpnička, Ferrocenes: Ligands, Materials and Biomolecules 2008 Wiley-VCH Chichester (Chapter 13)
14. C.G. Hartinger, and P.J. Dyson J. Chem. Soc. Rev. 38 2009 391 402
15. E. Meggers Curr. Opin. Chem. Biol. 11 2007 287 292
16. G. Gasser, I. Ott, and N. Metzler-Nolte J. Med. Chem. 54 2011 3 25
17. C. Ornelas New J. Chem. 35 2011 1973 1985
18. G. Jaouen, and N. Metzler-Nolte Medicinal Organometallic Chemistry in a series Topics in Organometallic Chemistry vol. 32 2010 Springer
19. S.-Ch. Chen J. Organomet. Chem. 202 1980 183 189
20. C. Price, M. Aslanoglu, Ch. J. Isaac, M.R.J. Elsegood, W. Clegg, B.R. Horrocks, and A. Houlton J. Chem. Soc. Dalton Trans. 1996 4115 4120
21. A. Houlton, Ch. J. Isaac, A.E. Gibson, B.R. Horrocks, W. Clegg, and M.R.J. Elsegood J.Chem. Soc. Dalton Trans. 1999 3229 3234
22. G. Gasser, M.J. Belousoff, A.M. Bond, and L. Spiccia J. Org. Chem. 71 2006 7565 7573
23. A.N. Patwa, S. Gupta, R.G. Gonnade, V.A. Kumar, M.M. Bhadbhade, and K.N. Ganesh J. Org. Chem. 73 2008 1508 1515
24. A.N. Patwa, R.G. Gonnade, V.A. Kumar, M.M. Bhadbhade, and K.N. Ganesh J. Org. Chem. 75 2010 8705 8708
25. H.V. Nguyen, A. Sallustrau, L. Male, P.J. Thornton, and J.H.R. Tucker Organometallics 30 2011 5284 5290
26. S. Top, A. Vessires, G. Leclerq, J. Quivy, J. Tang, J. Vaissermann, M. Huch, and G. Jaouen Chem. Eur. J. 9 2003 5223 5236
27. E.A. Hillard, A. Vessires, L. Thouin, G. Jaouen, and C. Amatore Angew. Chem. Int. Ed. 45 2006 285 290
28. D. Hamels, P. Dansette, E.A. Hillard, S. Top, P. Pigeon, G. Jaouen, and D. Mansuy Angew. Chem. Int. Ed. 48 2009 9124 9126
29. M. Hocek, P. Štěpnička, J. Ludvik, J. Cisařová, J. Votruba, D. Řeha, and P. Hobza Chem. Eur. J. 10 2004 2058 2066
30. P. James, J. Neudörfl, M. Eissmann, P. Jesse, A. Prokop, and H.-G. Schmalz Org. Lett. 13 2006 2763 2766
31. A.A. Simenel, E.A. Morozova, L.V. Snegur, S.J. Zykova, V.V. Kachala, L.A. Ostrovskaya, N.V. Bluchterova, and M.M. Fomina Appl. Organometal. Chem. 23 2009 219 224
32. A.A. Simenel, G.A. Dokuchaeva, L.V. Snegur, A.N. Rodionov, M.M. Iiyin, S.J. Zykova, L.A. Ostrovskaya, N.V. Bluchterova, M.M. Fomina, and V.A. Rikova Appl. Organometal. Chem. 25 2011 70 75
33. S. Trakossas, E. Coutouli-Argyropoulou, and D.J. Hadjipavlou-Litina Tetrahedron Lett. 52 2011 1673 1676
34. M. Bartholomä, A.R. Vortherms, S. Hillier, B. Ploier, J. Joyal, J. Babich, R.P. Doyle, and J. Zubieta ChemMedChem 5 2010 1513 1529
35. I. Ott, K. Kowalski, R. Gust, J. Maurer, P. Mücke, and R.F. Winter Bioorg. Med. Chem. Lett. 20 2010 866 869
36. K. Kowalski, A. Vessires, S. Top, G. Jaouen, and J. Zakrzewski Tetrahedron Lett. 44 2003 2749 2751
37. K. Kowalski, and J. Zakrzewski J. Organomet. Chem. 668 2003 91 94
38. K. Kowalski, N. Suwaki, J. Zakrzewski, A.J.P. White, N.J. Long, and D.J. Mann Dalton Trans. 2007 743 748
39. E. Coutouli-Argyropoulou, M. Tsitabani, G. Petrantonakis, A. Terzis, and C. Raptopoulou Org. Biomol. Chem. 1 2003 1382 1388
40. V.S. Sudhir, N.B.R. Baig, and S. Chandrasekaran Eur. J. Org. Chem. 2009 5365 5372
41. L. Schwink, P. Knochel, T. Eberle, and J. Okuda Organometallics 17 1997 7 9
42. O. Dogan, V. Senol, S. Zeytinci, H. Koyuncu, and A. Bulut J. Organomet. Chem. 690 2005 430 434
43. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, A. Ricci, A. Alberti, D. Macciantelli, M. Marcaccio, and S. Roffia Eur. J. Org. Chem. 3 2002 543 550
44. M.V. Lebedev, V.G. Nenajdenko, and E.S. Balenkova Synthesis 1 1998 89 93
45. S. Kaluz, and S. Toma Collect. Czech. Chem. Commun. 51 1986 2199 2206
46. A. Hameed, A. Rybarczyk-Pirek, and J. Zakrzewski J. Organomet. Chem. 656 2002 102 107
47. A. Kłys, Rybarczyk-Pirek, and J. Zakrzewski J. Organomet. Chem. 693 2008 1166 1170
48. B. Mucha, A. Kłys, A. Rybarczyk-Pirek, and J. Zakrzewski Tetrahedron Asymm 18 2007 1766 1768
49. M.C. Etter, J.C. MacDonald, and J. Bernstein Acta Crystallogr. Sect. B. 1994 617
50. K. Kowalski, R.F. Winter, A. Makal, A. Pazio, and K. Woźniak Eur. J. Inorg. Chem. 2009 4069 4077
51. W.L. Davis, R.F. Shago, E.H.G. Langer, and J.C. Swarts Polyhedron 24 2005 1611 1616
52. S. Sakanishi, D.A. Bradwell, S. Couchman, J.C. Jeffery, J. McCleverty, and M.D. Ward J. Organomet. Chem. 528 1997 35 45
53. P. Štěpnička, and I. Cisařová Inorg. Chem. 45 2006 8785 8798
54. A.C. Ohs, A.L. Rheingold, M.J. Shaw, and Ch. Nataro Organometallics 23 2004 4655 4660
55. J. Zakrzewski Inorg. Chim. Acta 278 1998 101 102
56. J. Silver, J. Zakrzewski, A. Tosik, and M. Bukowska-Strzyewska J. Organomet. Chem. 540 1997 169 174
57. G.M. Sheldrick Acta Crystallogr. A64 2008 112 122
58. L.J. Farrugia J. Appl. Cryst 32 1999 837 838
59. M. Nardelli J. Appl. Crystallogr. 29 1996 296 300
60. A.L. Spek PLATON - Molecular Geometry Program 1998 University of Utrecht The Netherlands
61. Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
62. J. Carmichael, W.G. Graff, A.F. Gazdar, J.D. Minna, and J.B. Mitchell Cancer Res. 47 1987 943 946