QSAR modeling of a set of pyrazinoate esters as antituberculosis prodrugs

Archiv der Pharmazie

Volumn 343, Issue 2, 2010, Pages 91-97

  Dos Santos Fernandes, João Paulo ^a,b   Pasqualoto, Kerly F M ^a   Felli, Veni M A ^a   Ferreira, Elizabeth I ^a   Brandt, Carlos A ^c  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b University of ABC   (Brazil)

^c INSTITUTO BUTANTAN   (Brazil)

Author keywords

Genetic algorithm; Molecular dynamics; Molecular modeling; Pyrazinoic acid esters; Structure activity relationship (SAR)

Indexed keywords

ESTER DERIVATIVE; OCTANOL; PRODRUG; PYRAZINOIC ACID DERIVATIVE; TUBERCULOSTATIC AGENT; WATER;

ARTICLE; DIPOLE; MODEL; NONHUMAN; PARTITION COEFFICIENT; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ALGORITHMS; ANTITUBERCULAR AGENTS; DRUG DESIGN; ESTERS; LEAST-SQUARES ANALYSIS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MYCOBACTERIUM TUBERCULOSIS; PRODRUGS; PYRAZINAMIDE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77149154636     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.200900216     Document Type: Article

References (39)

1. World Health Organization in WHO Report 2009 - "Global Tuberculosis Control: Epidemiology, Strategy, Financing", WHO Press, Geneva, 2009, pp. 6-33.
2. M. Silva, E. I. Ferreira, Rev. Bras. Ciên. Farm. 1999, 35, 17-30.
3. K. F. M. Pasqualoto, E. I. Ferreira, Curr. Drug Targets 2001, 2, 427-437.
4. P. J. Brennan, H. Nikaido, Annu. Rev. Biochem. 1995, 64, 29-63.
5. C. E. Barry III, R. E. Lee, K. Mdluli, A. E. Sampson, et al., Prog. Lipid Res. 1998, 37, 143-179.
6. J. Liu, C. E. Barry III, G. S. Besra, H. Nikaido, J. Biol. Chem. 1996, 271, 29545-29551.
7. S. Kushner, H. Dalalian, J. L. Sanjurjo, F. L. Bach Jr., et al., J. Am. Chem. Soc. 1952, 74, 3617-3621.
8. M. H. Cynamon, S. P. Klemens, T. S. Chou, R. H. Gimi, J. T. Welch, J. Med. Chem. 1992, 35, 1212-1215.
9. M. H. Cynamon, R. Gimi, F. Gyenes, C. A. Sharpe, et al., J. Med. Chem. 1995, 38, 3902-3907.
10. K. E. Bergmann, M. H. Cynamon, J. T. Welch, J. Med. Chem. 1996, 39, 3394-3400.
11. K. Konno, F. M. Feldmann, W. McDermott, Am. Rev. Res. Dis. 1967, 95, 461-469.
12. Y. Zhang, M. M. Wade, A. Scorpio, H. Zhang, et al., J. Antimicrob. Chemother. 2003, 52, 790-795.
13. K. F. M. Pasqualoto, E. I. Ferreira, O. A. Santos-Filho, A. J. Hopfinger, J. Med. Chem. 2004, 47, 3755-3764.
14. D. Rogers in WOLF Reference Manual version 5.5, The Chem21 Group, Inc., Chicago, IL, 1994.
15. A. T. Balaban, Chem. Phys. Lett. 1982, 89, 399-404.
16. V. Rastija, M. Medic-Saric, Eur. J. Med. Chem. 2009, 44, 400-408.
17. X. Ma, C. Chen, J. Yang, Acta Pharmacol. Sin. 2005, 26, 500-512.
18. C. Hansch, A. Leo, D. Hoekman (Eds.) Exploring QSAR - Hydrophobic, Electronic and Steric Constants, ACS Professional Reference Book, 1995.
19. L. L. Chen, J. Yao, J. B. Yang, J. Yang, Acta Pharmacol. Sin. 2005, 26, 1322-1333.
20. M. Iyer, R. Mishru, Y. Han, A. J. Hopfinger, Pharm. Res. 2002, 19, 1611-1621.
21. V. Tantishaiyakul, Pharmazie 2001, 56, 407-411.
22. J. P. S. Fernandes, M.Sc. Dissertation, University of São Paulo, Brazil, 2006.
23. J. P. S. Fernandes, V. M. A. Felli, Quím. Nova 2009, 32, 2464 - 2466.
24. S. G. Franzblau, R. S. Witzig, J. C. McLaughlin, P. Torres, et al., J. Clin. Microbiol. 1998, 32, 362-366.
25. R. D. Brown, Y. C. Martin, J. Chem. Inf. Comput. Sci. 1996, 36, 572-584.
26. HyperChem Program Release 7.51 for Windows, Hypercube, Inc., Gainesville, FL, 2002.
27. A. H. Wang, G. Ughetto, G. J. Quigley, A. Rich, J. Biomol. Struct. Dyn. 1986, 4, 319-342.
28. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
29. D. Doherty MOLSIM: Molecular Mechanics and Dynamics Simulation Software, UserMs Guide, version 3.2, The Chem21 Group, Inc., Lake Forest, IL, 1997.
30. Gaussian 03W version 6.0 revision A.1, Gaussian, Inc., Pittsburg, PA, 2003.
31. Marvin Beans version 5.1.5, ChemAxon, Ltd., Budapest, HUN, 2009.
32. W. G. Glen, W. J. Dunn III, D. R. Scott, Tetrahedron Comput. Methodol. 1989, 2, 349-354.
33. D. Rogers, A. J. Hopfinger, J. Chem. Inf. Comput. Sci. 1994, 34, 854-866.
34. L. M. Shi, Y. Fan, T. G. Myers, P. M. O'Connor, et al., J. Chem. Inf. Comput. Sci. 1998, 38, 189-199.
35. S. Wold, L. Eriksson, Statistical Validation in QSAR Results in Chemometric methods in molecular design (Ed.: H. van de Waterbeemd), VCH, Weinheim, 1995, pp. 61-88.
36. S. Geisser, J. Am. Stat. Assoc. 1975, 70, 320-328.
37. H. Kubinyi in Handbook of chemoinformatics, (Ed.: J. Gasteiger) Wiley-VCH, Weinheim, 2003, pp. 1532-1554.
38. A. Tropsha, P. Gramatica, V. K. Gombar, QSAR Comb. Sci. 2003, 22, 69-77.
39. A. Golbraikh, A. Tropsha, J. Mol. Graph. Model. 2002, 20, 269-276.