Synthesis and structural characterization of ferrocenyl-substituted aurones, flavones, and flavonols

Organometallics

Volumn 30, Issue 20, 2011, Pages 5424-5432

  Tiwari, Keshri Nath ^a,b   Monserrat, Jean Philippe ^a,b   De Montigny, Fréderic ^a,b   Jaouen, Gérard ^a,b   Rager, Marie Noelle ^c   Hillard, Elizabeth ^a,b  

^a PSL RESEARCH UNIVERSITY   (France)

^b CNRS   (France)

^c PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVE MOLECULES; BIPHASIC REACTION; CHALCONES; CYCLOPENTADIENYL RINGS; ELECTRON-DONATING GROUP; ELECTRONWITHDRAWING; EXO-CYCLIZATION; FERROCENES; FERROCENYL; NMR AND X-RAY; RING OPENING; SATURATED COLORS; STRUCTURAL CHARACTERIZATION; VISIBLE REGION;

IRON COMPOUNDS; ISOMERS; NEGATIVE IONS; REACTION INTERMEDIATES; X RAY CRYSTALLOGRAPHY;

SYNTHESIS (CHEMICAL);

EID: 80054773962     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200644e     Document Type: Article

References (65)

1. Link, A.; Balaguer, F.; Goel, A. Biochem. Pharmacol. 2010, 80, 1771-1792
2. Perez-Vizcaino, F.; Duarte, J. Mol. Aspects Med. 2010, 31, 478-494
3. Bisht, K.; Wagner, K.-H.; Bulmer, A. C. Toxicology 2009, 278, 88-100
4. Kaur, K.; Jain, M.; Kaur, T.; Jain, R. Bioorg. Med. Chem. 2009, 17, 3229-3256
5. Naithani, R.; Huma, L. C.; Holland, L. E.; Shukla, D.; McCormick, D. L.; Mehta, R. G.; Moriarty, R. M. Mini Rev. Med. Chem. 2008, 8, 1106-1133
6. Quideau, S.; Deffieux, D.; Douat-Casassus, C.; Pouységu, L. Angew. Chem., Int. Ed. 2011, 50, 586-621
7. Shanmugam, M.; Kannaiyan, R.; Sethi, G. Nutr. Cancer 2011, 63, 161-173
8. Spencer, J. Proc. Nutr. Soc. 2010, 69, 244-260
9. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931-5985
10. Hillard, E. A.; Vessières, A.; Jaouen, G. In TopOrgan; Springer Verlag: Berlin, 2010; Vol. 32, pp 81-117.
11. Metzler-Nolte, N.; Salmain, M. In Ferrocenes: Ligands, Materials and Biomolecules; Stepnicka, P., Ed.; Wiley: New York, 2008; pp 499-639.
12. Snegur, L. V.; Babin, V. N.; Simenel, A. A.; Nekrasov, Yu. S.; Ostrovskaya, L. A.; Sergeeva, N. S. Russ. Chem. Bull. Int. Ed. 2010, 59, 2167-2178
13. Hillard, E. A.; Vessières, A.; Thouin, L.; Jaouen, G.; Amatore, C. Angew. Chem., Int. Ed. 2006, 45, 285-290
14. Spencer, J.; Amin, J.; Wang, M.; Packham, G.; Alwi, S. S. S.; Tizzard, G. J.; Coles, S. J.; Paranal, R. M.; Bradner, J. E.; Heightman, T. D. Med. Chem. Lett. 2011, 2, 358-362
15. Arezki, A.; Brulé, E.; Jaouen, G. Organometallics 2009, 28, 1606-1609
16. Quirante, J.; Dubar, F.; González, A.; Lopez, C.; Cascante, M.; Cortés, R.; Forfar, I.; Pradines, B.; Biot, C. J. Organomet. Chem. 2011, 696, 1011-1017
17. Spencer, J.; Mendham, A. P.; Kotha, A. K.; Richardson, S. C. W.; Hillard, E. A.; Jaouen, G.; Male, L.; Hursthouse, M. B. Dalton Trans. 2009, 918-921
18. N'Da, D.; Breytenbach, J.; Smith, P.; Lategan, C. Arzneimittel-forschung 2010, 60, 627-635
19. Hillard, E. A.; Jaouen, G. Organometallics 2011, 30, 20-27.
20. Sumathi, S.; Tharmaraj, P.; Sheela, C. D.; Ebenezer, R. J. Coord. Chem. 2011, 64, 1707-1717
21. Baluja, S.; Movaliya, J.; Bhalodia, R. J. Instit. Chem. (India) 2009, 81, 102-109
22. Devi, J. M.; Tharmaraj, P.; Ramakrishnan, S. K.; Ramachandran, K. Mater. Lett. 2008, 62, 852-856
23. Li, X.; Sun, H.; Floerke, U.; Klein, H.-F. Organometallics 2005, 24, 4347-4350
24. Natarajan, C.; Palaniandavar, M. J. Indian Chem. Soc. 1983, 60, 1-6
25. Tambatkar, G. D.; Meshram, Y. K.; Gadpayale, M. R.; Bhutada, P. G.; Kurhade, G. H. Asian J. Chem. 2008, 20, 5414-5418
26. Karamunge, K. G.; Vibhute, Y. B. Pol. J. Chem. 2008, 82, 559-564
27. Chen, W.; Sun, S.; Wei, C.; Liang, Y.; Song, J. J. Mol. Struct. 2009, 918, 194-197
28. Kostyuk, V. A.; Potapovich, A. I.; Kostyuk, T. V.; Cherian, M. G. Cell. Mol. Biol. 2007, 53, 62-69
29. de Souza, R. F. V.; De Giovani, W. F. Spectrochim. Acta, Part A 2005, 61A, 1985-1990
30. Kostyuk, V. A.; Potapovich, A. I.; Vladykovskaya, E. N.; Korkina, L. G.; Afanas'ev, I. B. A. Arch. Biochem. Biophys. 2001, 385, 129-137
31. Zutin, K.; Nogueira, V. M.; Mauro, A. E.; Melnikov, P.; Iluykhin, A. Polyhedron 2001, 20, 1011-1016
32. Kuramshin, A. I.; Karpenko, E. A.; Cherkasov, R. A. Russ. J. Gen. Chem. 2001, 71, 191-195
33. Anson, C. E.; Creaser, C. S.; Malkov, A. V.; Mojovic, L.; Stephenson, G. R. J. Organomet. Chem. 2003, 668, 101-122
34. Malkov, A. V.; Mojovic, L.; Stephenson, G. R.; Turner, A. T.; Creaser, C. S. J. Organomet. Chem. 1999, 589, 103-110
35. Wu, X.; Tiekink, E. R. T.; Kostetski, I.; Kocherginsky, N.; Tan, A. L. C.; Khoo, S. B.; Wilairat, P.; Go, M.-L. Eur. J. Pharm. Sci. 2006, 27, 175-187
36. Hauser, C. R.; Lindsay, J. K. J. Org. Chem. 1957, 22, 482-485
37. Zsoldos-Mady, V.; Csampai, A.; Szabo, R.; Meszaros-Alapi, E.; Pasztor, J.; Hudecz, F.; Sohar, P. ChemMedChem 2006, 1, 1119-1125
38. Wu, X.; Wilairat, P.; Go, M. L. Bioorg. Med. Chem. Lett. 2002, 12, 2299-2302
39. Ferle-Vidovic, A.; Poljak-Blazi, M.; Rapic, V.; Skare, D. Cancer Biother. Radiopharm. 2000, 15, 617-624
40. Monserrat, J.-P.; Chabot, G. G.; Hamon, L.; Quentin, L.; Scherman, D.; Jaouen, G.; Hillard, E. A. Chem. Commun. 2010, 46, 5145-5147
41. Gleiter, R.; Seeger, R.; Binder, H.; Fluck, E.; Cais, M. Angew. Chem., Int. Ed. Engl. 1972, 11, 1028-1030
42. Agrawal, N. N.; Soni, P. A. Indian J. Chem. 2006, 45B, 1301-1303
43. Grundon, M. F.; Stewart, D.; Watts, W. E. J. Chem. Soc., Chem. Commun. 1975, 772-773
44. Grundon, M. F.; Stewart, D.; Watts, W. E. Proc. R. Ir. Acad. 1989, 89B, 185-196
45. Sekizaki, H. Bull. Chem. Soc. Jpn. 1988, 61, 1407-1409
46. Lévai, A.; Tõkés, A. Synth. Commun. 1982, 12, 701-707
47. Kurosawa, K.; Higuchi, J. Bull. Chem. Soc. Jpn. 1972, 45, 1132-1136
48. Kurosawa, K. Bull. Chem. Soc. Jpn. 1969, 42, 1456-1458
49. Rao, Y. K.; Fang, S.-H.; Tzeng, Y.-M. Bioorg. Med. Chem. 2005, 13, 6850-6855
50. Kasahara, A.; Izumi, T.; Oshima, M. Bull. Chem. Soc. Jpn. 1974, 47, 2526-2528
51. Meyer-Dayan, M.; Bodo, B.; Deschamps-Vallet, C.; Molho, D. Tetrahedron Lett. 1978, 19, 3359-3360
52. Fitzgerald, D. M.; O'Sullivan, J. F.; Philbin, E. M.; Wheeler, T. S. J. Chem. Soc. 1955, 860-862
53. Costa, A. M. B. S. R. C. S.; Dean, F. M.; Jones, M. A.; Varma, R. S. J. Chem. Soc., Perkin Trans. 1 1985, 799-808
54. Garcia, H.; Iborra, S.; Primo, J.; Miranda, M. A. J. Org. Chem. 1986, 51, 4432-4436
55. Harkat, H.; Blanc, A.; Weibel, J.-M.; Pale, P. J. Org. Chem. 2008, 73, 1620-1623
56. Algar, J.; Flynn, J. P. Proc. R. Ir. Acad., Sect. B 1934, B42, 1-8
57. Oyamada, B. J. Chem. Soc. Japan 1934, 55, 1256-1261
58. Adam, W.; Golsch, D.; Hadjiarapoglou, L. J. Org. Chem. 1991, 56, 7292-7297
59. El Sous, M.; Khoo, M.; Holloway, G.; Owen, D.; Scammells, P.; Rizzacasa, M. Angew. Chem., Int. Ed. 2007, 46, 7835-7838
60. Venkateswarlu, S.; Panchagnula, G. K.; Guraiah, M. B.; Subbaraju, G. V. Tetrahedron 2005, 61, 3013-3017
61. Venkateswarlu, S.; Panchagnula, G. K.; Gottumukkala, A. L.; Subbaraju, G. V. Tetrahedron 2007, 63, 6909-6914
62. Breitmaier, E.; Voelter, W., Eds. Carbon-13 NMR Spectroscopy; VCH Publishers Inc.: Deerfield Beach, 1987.
63. Barlow, S.; Marder, S. R. Chem. Commun. 2000, 1555-1562
64. Xue, Y.; Mou, J.; Liu, Y.; Gon, X.; Yang, Y.; An, L. Cent. Eur. J. Chem. 2010, 8, 928-936
65. Monserrat, J.-P.; Al-Safi, R. I.; Tiwari, K. N.; Quentin, L.; Chabot, G. G.; Vessières, A.; Jaouen, G.; Neamati, N.; Hillard, E. A. Bioorg. Med. Chem. Lett. 2011, in press, doi: 10.1016/j.bmcl.2011.07.078.