Characterization of electronic structure and physicochemical properties of antiparasitic nifurtimox analogues: A theoretical study

International Journal of Quantum Chemistry

Volumn 108, Issue 8, 2008, Pages 1369-1379

  Soriano Correa, Catalina ^a   Raya, A ^a   Esquivel, Rodolfo O ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b DEPARTAMENTO DE QUÍMICA   (Mexico)

Author keywords

Ab initio calculations; Antiparasitic; Chagas' disease; Nifurtimox analogues; Nitrofurans

Indexed keywords

ELECTRONIC STRUCTURE; FREE RADICALS; OXIDATIVE STRESS;

ANTIPARASITIC; NIFURTIMOX ANALOGUES; NITROFURANS;

DISEASES;

EID: 42449108245     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.21633     Document Type: Article

References (37)

1. Kollien, A. H.; Schaub, G. A. Parasitol Today 2000, 16, 381.
2. Foye, W. O.; Lemke, T. L.; Williams, D. A. Principles of Medicinal Chemistry; Lippincot Williams and Wilkins: Philadelphia, PA, 1995; Chapter 35.
3. Boveris, A.; Sies, H.; Martino, E. E.; Docampo, R.; Turrens, J. F.; Stoppani, A. O. M. Biochem J 1980, 188, 643.
4. Maya, J. D.; Bollo, S.; Nuñez-Vergara, L. J.; Squella, J. A.; Repetto, Y.; Morello, A.; Périé, J.; Chauvière, G. Biochem Pharmacol 2003, 65, 999.
5. Viodé, C.; Bettache, N.; Cenas, N.; Krauth-Siegel, R. L.; Chauvière, G.; Bakalara, N.; Périé, J. Biochem Pharmacol 1999, 57, 549.
6. Gerpe, A.; Odreman-Nuñez, I.; Draper, P.; Boiani, L.; Urbina, J. A.; González, M.; Cerecetto, H. Bioorg Med Chem 2008, 16, 569.
7. Hankins, E. G.; Gillespie, J. R.; Aikenhead, K.; Buckner, F. S. Mol Biochem Parasitol 2005, 144, 68.
8. Viodé, C. Biochem Pharm 1999, 57, 549.
9. Voogd, C. E.; van der Stel J. J.; Jacobs J. J. Mutat Res 1979, 66, 207.
10. Rosselli, F. P.; Albuquerque, C. N.; da Silva, A. B. F. Int J Quantum Chem 2005, 103, 738.
11. Flores-Holguín, N.; Glossman-Mitnik, D. J Mol Struct (Theochem) 2005, 723, 231.
12. Flores-Holguín, N.; Glossman-Mitnik, D. J Mol Struct (Theochem) 2004, 681, 77.
13. Flores-Holguín, N.; Glossman-Mitnik, D. J Mol Struct (Theochem) 2005, 717, 1.
14. Monasterios, M.; Escorche, M.; Avendaño, M. J Mol Struct (Theochem) 2005, 748, 49.
15. Soriano-Correa, C.; Raya, A.; Sánchez-Ruiz, J. F.; Esquivel, R. O. Int J Quantum Chem 2005, 104, 491.
16. Pozas, R.; Carballo, J.; Castro, C.; Rubio, J. Bioinorg Med Chem Lett 2005, 15, 1417.
17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Revision A. 7; Gaussian: Pittsburgh, PA, 1998.
18. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
19. Duchovic, R. J.; Hase, W. L.; Schlegel, H. B.; Frisch, M. J.; Raghavachari, K. Chem Phys Lett 1981, 85, 145.
20. Schlegel, H. B.; McDouall, J. J. W. In Computational Advances in Organic Chemistry; Ogretir, C.; Csizmadia, I. G., Eds.; NATO-ASI Series C 330; Kluwer Academic: The Netherlands, 1991; pp 167-185.
21. Foresman, A.; Frisch, M. J. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian: Pittsburgh, PA, 1995.
22. Dehareng, D.; Dive, G. J Comput Chem 2000, 21, 483.
23. Mölder, U.; Burk, P.; Koppel, I. A. Int J Quantum Chem 2001, 82, 73.
24. Soriano-Correa, C.; Esquivel, O. R.; Sagar, R. P. Int J Quantum Chem 2003, 94, 165.
25. Politzer, P.; Truhlar, D. G. Chemical Applications of Atomic and Molecular Electrostatic Potentials; Academic Press: New York, 1981.
26. Mayer, I. Int J Quantum Chem 1986, 29, 477.
27. Koopmans, T. A. Physica 1933, 1, 104.
28. Parr, R. G.; Pearson, R. G. J Am Chem Soc 1983, 105, 7512.
29. Parr, R. G.; Szentpály, L. V.; Liu, S. J Am Chem Soc 1922, 1999, 121.
30. Parr, R. G.; Yang W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
31. Pearson, R. G. Proc Natl Acad Sci USA 1986, 83, 8440.
32. Soriano-Correa, C.; Sánchez-Ruiz, J. F.; Raya, A.; Esquivel, R. O. Int J Quantum Chem 2007, 107, 628.
33. Chattaraj, P. K.; Sarkar, U.; Roy, D. R. Chem Rev 2006, 106, 2065.
34. Chattaraj, P. K.; Lee, H.; Parr, R. G. J Am Chem Soc 1991, 113, 1855.
35. Chamorro, E.; Chattaraj, P. K.; Fuentealba, P. J Phys Chem A 2003, 107, 7068.
36. Chattaraj, P. K.; Sengupta, S. J Phys Chem 1996, 100, 16126.
37. Docampo, R.; Moreno, S. N. J Rev Infect Dis 1984, 6, 223.