Conformational study of the four main dipyrone metabolites through theoretical methods: Electrostatic potential maps and NBO calculations

Journal of Molecular Structure: THEOCHEM

Volumn 815, Issue 1-3, 2007, Pages 75-81

  Bocca, Cleverson C ^a   Basso, Ernani A ^a   Mosquetta, Rafael ^a  

^a STATE UNIVERSITY OF MARINGÁ   (Brazil)

Author keywords

Dipyrone; Metabolites; NBO analysis; Theoretical calculations

Indexed keywords

EID: 84961983426     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2007.03.022     Document Type: Article

References (40)

1. Gladtke E. Am. J. Med. 75 (1983) 121
2. Brogden R.N. Drugs 32 Suppl. 4 (1986) 60
3. Wong A., Sibbald A., Ferrero F., Plager M., Santolaya M.E., Escobar A.M., Campos S., Barragan S., De M., Gonzalez L., and Kesselring G.L. Clin. Pediatr. (Phil.) 40 (2001) 313
4. Zylber-Katz E., Granit L., and Levy M. Eur. J. Clin. Pharmacol. 42 (1992) 187
5. Levy M., Zylber-Katz E., and Rosenkranz B. Clin. Pharmacokinet. 28 (1995) 216-234
6. Ergün H., Frattarelli D.A.C., and Aranda J.V. J. Pharm. Biomed Anal. 35 (2004) 479-487
7. Rohdewald P., Drehsen G., Milsmann E., and Derendorf H. Arzneimittelforschung 33 (1983) 985-988
8. Levy M. Thorax 55 (2000) 72-74
9. Graham G.G., and Scott K.F. Inflammopharmacology 11 (2003) 401-413
10. Bentur Y., and Cohen O. J. Toxicol. Clin. Toxicol. 42 (2004) 261-265
11. Kurumbail R.G., Kiefer J.R., and Marnett L. J. Curr. Opin. Struct. Biol. 11 (2001) 752-760
12. Kujubu D.A., Fletcher B.S., Varnum B.C., Lim R.W., and Herschman H.R. J. Biol. Chem. 266 (1991) 12866-12872
13. Smith W.L., Sonnenburg W.K., Allen M.L., Watanabe T., Zhu J., and El-Harith E.A. Renal Eicosanoids (1989), Plenum pp. 131-148
14. Kujubu D.A., Fletcher B.S., Varnum B.C., Lim R.W., and Herschman H.R. J. Biol. Chem. 266 (1991) 12866-12872
15. Lee S.H., Soyoola E., Chanmugam P., Hart S., Sun W., Zhong H., Liou S., Simmons D., and Hwang D. J. Biol. Chem. 267 (1992) 25934-25938
16. DeWitt D.L., and Meade E.A. Arch. Biochem. Biophys. 306 (1993) 94-102
17. Picot D., Loll P.J., and Garavito R.M. Nature 367 (1994) 243-249
18. Kurumbail R.G., Stevens A.M., Gierse J.K., McDonald J.J., Stegeman R.A., Pak J.Y., Gildehaus D., Miyashiro J.M., Penning T.D., Seibert K., Isakson P.C., and Stallings W.C. Nature 384 (1996) 644-648
19. Campos C., De Gregorio R., Garci{dotless}a-Nieto R., Gago F., Ortiz P., and Alemany S. Eur. J. Pharm. 378 (1999) 339-347
20. Uetrecht P., Ma H.M.J., MacKnight E., and McClelland R. Chem. Res. Toxicol. 8 (1995) 226-233
21. Ibáñez L., Vidal X., Ballari{dotless}́n E., and Laporte J.R. Eur. J. Clin. Pharmacol. 60 (2005) 821-829
22. Hedenmalm K., and Spigset O. Eur. J. Clin. Pharmacol. 58 (2002) 265-274
23. Chan T.Y.K., and Chan A.W.K. Pharmacoepidemiol. Drug Saf. 5 (1996) 215-219
24. Ries C.A., and Sahud M.A. J. Am. Med. Assoc. 231 (1975) 352-355
25. Ergun H., Uzbay I.T., Celik T., Kayir H., Yesilyurt O., and Tulunay F.C. Drug Dev. Res. 53 (2001) 254-259
26. Pompeia C., Boaventura M.F., and Curi R. Int. Immunopharmacol. 1 (2001) 2173-2182
27. Ergun H., Ayhan I.H., and Tulunay F.C. Gen. Pharmacol. 33 (1999) 237-241
28. M.J. Risch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, V. Ortiz, Q.J. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, J.D. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Guassian 03, revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
29. Hehre J. A Guide to Molecular Mechanics and Quantum Chemical Calculations (2003), Wavefunction, Inc., Irvine, CA, USA Chap. 4 and 19
30. Politzer J.S., and Murray M.C. Int. J. Quantum Chem. 88 (2002) 19
31. MOLEKEL 4.3, P.H.P. Flükiger, S. Lüthi, J. Portmann, Weber, Swiss Center for Scientic Computing, Manno (Switzerland), 2000-2002.
32. Onsager L.J. Am. Chem. Soc. 58 (1938) 1486
33. Miertus S., Scrocco E., and Tomasi J. Chem. Phys. 55 (1981) 117
34. Bocca C.C., Basso E.A., and Gauze G.F. Chem. Phys. Lett. 413 (2005) 434
35. Politzer K.C.D. In: Deb B.M. (Ed). The Force Concept in Chemistry (1981), Van Nostrand Reinhold, New York Chap. 6
36. Politzer J.S.M. In: Lipkowitz K.B., and Boyd D.B. (Eds). Reviews in Computational Chemistry 2 (1991), VCH Publishers, New York Chap. 7
37. Naray-Szabo G., and Ferenczy G.G. Chem. Rev. 95 (1995) 829
38. Murray S., and Politzer P. In: Shapes A.M. (Ed). Molecular Orbital Calculations for Biological Systems (1998), Oxford University Press, New York Chap. 3
39. Michaux C., et al. Eur. J. Med. Chem. 40 (2005) 1316
40. Weinhold F., and Landis C.R. Valency and Bonding. A Natural Bond Orbital Donor-Acceptor Perspective (2005), Cambridge University Press, Cambridge