Electronic and cytotoxic properties of 2-amino-naphtho[2,3-b]furan- 4,9-diones

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1634-1643

  Jiménez Alonso, Sandra ^a,b   Guasch, Judith ^c   Estévez Braun, Ana ^a,b   Ratera, Imma ^c   Veciana, Jaume ^c   Ravelo, Angel G ^a,b  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b Madrid Spain   (Spain)

^c BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BOND ACCEPTORS; CYTOTOXIC; ELECTRON DELOCALIZATION; ENERGY RELATIONSHIPS; HYDROGEN-BOND DONORS; INTRA-MOLECULAR ELECTRON TRANSFER; MOLECULAR ENVIRONMENT; REDOX POTENTIALS; SOLVATOCHROMIC PROPERTIES; SOLVATOCHROMISMS;

ELECTRONIC PROPERTIES; HYDROGEN; ORGANIC POLLUTANTS; REDOX REACTIONS;

AROMATIC COMPOUNDS;

2 BENZYLAMINO 3 CYCLOHEXYL NAPHTHO[2,3 B]FURAN 4,9 DIONE; 2 BENZYLAMINO 3 ETHYL NAPHTHO[2,3 B]FURAN 4,9 DIONE; 2 CYCLOHEXYLAMINO 3 ETHYLNAPHTHO[2,3 B]FURAN 4,9 DIONE; 2 CYCLOHEXYLAMINO 3 HEXYL NAPHTHO[2,3 B]FURAN 4,9 DIONE; 2 TERT BUTYLAMINO 3 ETHYL NAPHTHO[2,3 B]FURAN 4,9 DIONE; 2 TERT BUTYLAMINO 3 FURAN 3 YL NAPHTHO[2,3 B]FURAN 4,9 DIONE; 2 TERT BUTYLAMINO 3 PHENYL NAPHTHO[2,3 B]FURAN 4,9 DIONE; CYTOTOXIC AGENT; FURAN DERIVATIVE; HYDROGEN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CYTOTOXICITY; ELECTRON; ELECTRON TRANSPORT; HUMAN; HUMAN CELL; HYDROGEN BOND; MOLECULAR INTERACTION; OXIDATION REDUCTION POTENTIAL; QUANTITATIVE ANALYSIS; SOLVATION; SOLVATOCHROMISM;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ELECTRONS; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHOQUINONES; SOLVENTS;

EID: 79953893782     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102233j     Document Type: Article

References (72)

1. Hui, Y.; Khim Chng, E. L.; Lin Chng, C. Y.; Poh, H. L.; Webster, R. D. J. Am. Chem. Soc. 2009, 131, 1523-1534.
2. Ogawa, M.; Koyanagi, J.; Sugaya, A.; Tsuda, T.; Ohguchi, H.; Nakayama, K.; Yamamoto, K.; Tanaka, A. Biosci. Biotechnol. Biochem. 2006, 70, 1009-1012.
3. (a) Han, R. Stem Cells 1994, 12, 53-63
4. (b) Alvi, K. A.; Pu, H.; Luche, M.; Rice, A.; App, H.; McMahon, G.; Dare, H.; Margolis, B. J. Antibiot. 1999, 52, 215-223;
5. (c) Wang, X. W. Drugs Future 1999, 24, 613-617
6. (d) Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586-11593;
7. (e) Stahl, P.; Kissau, L.; Mazitschek, R.; Giannis, A.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 1174-1178
8. Angew. Chem. 2002, 114, 1222-1226.
9. Haraguchi, H.; Yokohama, K.; Oike, S.; Ito, M.; Nozaki, H. Arch. Microbiol. 1997, 167, 6-10.
10. Pérez-Sacau, E.; Estévez-Braun, A.; Ravelo, A. G.; Yapu, D. G.; Turba, A. G. Chem. Biodiversity 2005, 2, 264-274.
11. Campostakaki, G. M.; Steiman, R.; Seigle-Murandi, F.; Silva, A. A.; Bieber, L. Rev. Microbiol. 1992, 23, 106-111.
12. (a) DeSimone, R. W.; Currie, K. S.; Mitchell, S. A.; Darrow, J. W.; D. Pippin, A. Comb. Chem. High Throughput Screening 2004, 7, 473-491.
13. (b) Li, J.; Liu, K. K. C. Mini-Rev. Med. Chem. 2004, 4, 207-233.
14. (c) Li, J.; Liu, K.; Sakya, S. Mini-Rev. Med. Chem. 2005, 5, 1133-1144.
15. (d) Costantino, L.; Barlocco, D. Curr. Med. Chem. 2006, 13, 65-85.
16. (a) Driscoll, J. S.; Hazard, G. F.; Wood, H. B.; Golden, A. Cancer Chemother. Rep. Part 2 1974, 4, 1-27.
17. (b) Liu, K. K. C.; Li, J.; Sakya, S. Mini- Rev. Med. Chem. 2004, 4, 1105-1125.
18. (c) Jiménez-Alonso, S.; Estévez-Braun, A.;Zárate, R.; Ravelo, A. G.; López,M. Tetrahedron 2007, 63, 3066-3074.
19. (d) Jiménez-Alonso, S.; Chávez-Orellana, H.; Estévez-Braun, A.; Ravelo, A. G.; Feresin, G.; Tapia, A. Tetrahedron 2008, 64, 8938-8942.
20. (e) Jimenez-Alonso, S.; Chávez-Orellana, H.; Estévez-Braun, A.; Ravelo, A. G.; Perez-Sacau, E.; Machín, F. J. Med. Chem. 2008, 51, 6761-6772.
21. (f) Jimenez-Alonso, S.;Pérez-Lomas A. L.; Estévez-Braun, A.; Muñoz-Martinez, F.; Chávez-Orellana, H.; Ravelo, A. G.; Gamarro, F.; Castanys, S.; López, M. J. Med. Chem. 2008, 51, 7132-7143.
22. (a) Wardman, P. In Selective Activation of Drugs by Redox Processes; Adams, G. E., Breccia, A., Fielden, E. M., Wardman, P., Eds.; Plenum Press: New York, 1990; p 110.
23. (b) Bard, A. J.; Faulkner, R. L. In Electrochemical Methods, Fundamentals and Applications; John Wiley and Sons: New York, 2003.
24. (c) Hillard, E. A.; Caxico de Abreu, F.; Melo Ferreira, D. C.; Jaouen, G.; Goulart, M. O. F.; Amatore, C. Chem. Commun. 2008, 2612-2628.
25. (a) Hammerich, O. In Organic Electrochemistry; Lund, H., Hammerich, O., Eds.; Marcel Dekker, Inc.: New York, 2001; p 95.
26. (b) Amatore, C. In Organic Electrochemistry; Lund, H., Hammerich, O., Eds.; Marcel Dekker, Inc.: New York, 2001; p 1.
27. Begleiter, A.; Leith, M. K. Cancer Res. 1990, 50, 2872-2876.
28. (a) Hammerich, O.; Svensmark, B. In Organic Electrochemistry, 3rd ed.; Lund, H.;, Baizer, M. M., Eds.,; Marcel Dekker: New York, 1991; p 16.
29. (b) Chambers, J. Q. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; Wiley, New York, 1988; Vol. II, chapter 12, p 719.
30. (a) In Function of Quinones in Energy Conserving Systems; Trumpower, B. L., Ed.; Academic Press: New York, 1982.
31. (b) Thurnauer, M. C.; Brown, J. W.; Gast, P.; Feezel, L. L. Radiat. Phys. Chem. 1989, 34, 647-651.
32. (c) Van der Est, A. Biochim. Biophys. Acta 2001, 1507, 212-225.
33. (d) Rigby, S. E. J.; Evans, M. C. W.; Heathcote, P. Biochim. Biophys. Acta 2001, 1507, 247-259.
34. (e) Blankenship, R. E. In Molecular Mechanisms of Photosynthesis, 1st ed.; Blackwell Science: Oxford, 2002.
35. (f) Voet, D.; Voet, J. G. In Biochemistry, 3rd ed.; Wiley: New York,2004.
36. (g) Epel, B.; Niklas, J.; Sinnecker, S.; Zimmermann, H.; Lubitz, W. J. Phys. Chem. B 2006, 110, 11549-11560.
37. (a) Shiah, S. G.; Chuang, S. E.; Chau, Y. P.; Shen, S. C.; Kuo, M. L. Cancer Res. 1999, 59, 391-398
38. (b) Waris, G.; Ahsan, H. J. Carcinog. 2006, 5, 14.
39. Reichardt, C. iIn Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2003; chapter 6, pp 329-388.
40. Khajehpour, M.; Welch, C. M.; Kleiner, K. A.; Kauffman, J. F. J. Phys. Chem. A 2001, 105, 5372-5379.
41. Sasirekha, V.; Vanelle, P.; Terme, T.; Meenakshi, C.; Umadevi, M.; Ramakrishnan, V. J. Fluoresc. 2007, 17, 528-539.
42. Teimouri, M. B.; Khavasi, H. R. Tetrahedron 2007, 63, 10269-10275.
43. (a) Perez-Sacau, E.; Diaz-Peñate, R. G.; Estevez-Braun, A.; Ravelo, A. G.; Garcia-Castellano, J. M.; Pardo, L.; Campillo, M. J. Med. Chem. 2007, 50, 696-706.
44. (b) Zakharova, O. D.; Ovchinnikova, L. P.; Goryunov, L. I.; Troshkova, N. M.; Shteingarts, V. D.; Nevinsky, G. A. Eur. J. Med. Chem. 2010, 45, 2321-2326.
45. (c) Kanaan, Y. M.; White, D. F.; Das, J. R.; Berhe, S.; Bakare, O.; Kenguele, H.; Beyene, D.; Zhou, Y.; Day, A. A.; Copeland, R. L. Anticancer Res. 2010, 30, 519-528.
46. (d) Bonifazi, E. L.; Rios-Luci, C.; Leon, L. G.; Burton, G.; Padron, J. M.; Misico, R. I. Bioorg. Med. Chem. 2010, 18, 2621-2630.
47. (a) Tonholo, J.; Freitas, L. R.; de Abreu, F. C.; Azevedo, D. C.; Zani, C. L.; de Oliveira, A. B.; Goulart, M. O. F. J. Braz. Chem. Soc. 1998, 9, 163-169.
48. (b) Hillard, E. A.; Caxico de Abreu, F.; Melo Ferreira, D. C.; Jaouen, G.; Goulart, M. O. F.; Amatore, C. Chem. Commun. 2008, 2612- 2628.
49. Stallings, M. D.; Morrison, M. M.; Sawyer, D. T. Inorg. Chem. 1981, 20, 2655-2660.
50. (a) Kuder, J. E.; Wychick, D.; Miller, R. L.; Walker, M. S. J. Phys. Chem. 1974, 78, 1714-1718.
51. (b) Russel, C.; Jaenicke, W. J. Electroanal. Chem. 1986, 199, 139-151.
52. (c) Crawford, P. W.; Carlos, E.; Ellegood, J. C.; Cheng, C. C.; Dong, Q.; Liu, D. F.; Luo, Y. L. Electrochim. Acta 1996, 41, 2399-2403.
53. Jensen, B. S.; Parker, V. D. J. Chem. Soc., Chem. Commun. 1974, 367-368.
54. Ashnagar, A.; Bruce, P. L.; Dutton, P. L.; Prince, R. C. Biochim. Biophys. Acta 1984, 801, 351-359.
55. Inbaraj, J. J.; Krishna, M. C.; Gandhidasan, R.; Murugesan, R. Biochim. Biophys. Acta 1999, 1472, 462-470.
56. (a) Cotterill, A. S.; Moody, C. J.; Mortimer, R. J.; Norton, C. L.; O'Sullivan, N.; Stephens, M. A.; Stradiotto, N. R.; Swann, E.; Stratford, I. J. J. Med. Chem. 1994, 37, 3834-3843.
57. (b) Qabaja, G.; Jones, G. B. J. Org. Chem. 2000, 65, 7187-7194.
58. (c) Qabaja, G.; Perchellet, E. M.; Perchellet, J. P.; Jones, G. B. Tetrahedron Lett. 2000, 41, 3007-3010.
59. (a) Kunz, K. R.; Iyengar, B. S.; Dorr, R. T.; Alberts, D. S.; Remers, W. A. J. Med. Chem. 1991, 34, 2281-2286.
60. (b) Goulart, M. O. F.; Zani, C. L.; Tonholo, J.; Freitas, L. R.; de Abreu, F. C.; Oliveira, A. B.; Raslan, D. S.; Starling, S.; Chiari, E. Bioorg. Med. Chem. Lett. 1997, 7, 2043-2048.
61. (a) Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1976, 98, 377-383.
62. Taft, R. W.; Kamlet, M. J. J. Am. Chem. Soc. 1976, 98, 2886-2894.
63. (b) Taft, R. W.; Kamlet, M. J.; Abboud, J. L. J. Am. Chem. Soc. 1977, 99, 6027-6038.
64. (c) Kamlet, M. J.; Abboud, J. - L. M.; Taft, R. W. Prog. Phys. Org. Chem. 1981, 13, 485-630.
65. (d) Taft, R. W.; Kamlet, M. J.; Abboud, J. L. M. J. Am. Chem. Soc. 1981, 103, 1080-1086.
66. (e) Marcus, Y. Chem. Soc. Rev. 1993, 22, 409-416.
67. (f) Laurence, C.; Nicolet, P.; Dalati, M. T.; Abboud, J. L. M.; Notario, R. J. Phys. Chem. 1994, 98, 5807-5816.
68. (g) Abboud, J.L. M.; Notario, R. Pure Appl. Chem. 1999, 71, 645-718.
69. Ratera, I.; Sporer, C.; Ruiz-Molina, D.; Ventosa, N.; Baggerman, J.; Brouwer, A. M.; Rovira, C.; Veciana, J. J. Am. Chem. Soc. 2007, 129, 6117-6129.
70. Gutierrez, P. L. Nguyen, B. In Redox Chemistry and Interfacial Behaviour of Biological Molecules; Dryhurst, G., Niki, K., Eds.; Plenum Press: New York, 1988, pp 369-382.
71. Sutovsky, Y.; Likhtenshtein, G. I.; Bittner, S. Tetrahedron 2003, 59, 2939-2945.
72. Ventosa, N.; Ruiz-Molina, D.; Sedó, J.; Rovira, C.; Tmas, S.; André, J. J.; Bibier, A.; Veciana, J. Chem.-Eur. J. 1999, 5, 3533-3548.