A QSAR study of biphenyl analogues of 2-nitroimidazo-[2, 1-b] [1, 3]-oxazines as antitubercular agents using genetic function approximation

Medicinal Chemistry

Volumn 8, Issue 4, 2012, Pages 717-726

  Ray, Supratim ^a   Roy, Partha Pratim ^b  

^a Dr B C Roy College of Pharmacy and Allied Health Sciences   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

2 Nitroimidazo 2,1 b 1,3 oxazines; Antitubercular; GFA; QSAR

Indexed keywords

BIPHENYL DERIVATIVE; OXAZINE DERIVATIVE; TUBERCULOSTATIC AGENT;

ARTICLE; CHEMOMETRIC ANALYSIS; CONTROLLED STUDY; DRUG ACTIVITY; HYDROPHOBICITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

ANTITUBERCULAR AGENTS; BIPHENYL COMPOUNDS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; NITROIMIDAZOLES; OXAZINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 84863749846     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340612801216210     Document Type: Article

References (33)

1. WHO report on Global TB control report 2010 http://www.who.int/tb/ publications/global-report/2010/en/index.html
2. Guerrin-Tran, E.; Thiolet, J. M.; Rousseau, C.; Henry, S.; Poirier, C.; Che, D.; Vinas, J. M.; Jarlier, V.; Robert, J. An evaluation of data quality in a network for surveillance of Mycobacterium tuberculosis resistance to antituberculosis drugs in Ile-de-France region-2001-2002. Eur. J. Epidemiol., 2006, 21(10), 783-785.
3. Frieden, T. R.; Sterling, T. R.; Munsiff, S. S.; Watt, C. J.; Dye, C. Tuberculosis. Lancet, 2003, 362(9387), 887-899.
4. Matsumoto, M.; Hashizume, H.; Tsubouchi, H.; Sasaki, H.; Itotani, M.; Kuroda, H.; Tomishige, T.; Kawasaki, M.; Komatsu, M. Screening for novel antituberculosis agents that are effective against multidrug resistant tuberculosis. Curr. Top. Med. Chem., 2007, 7(5), 499-507.
5. Rivers, E. C.; Mancera, R. L. New anti-tuberculosis drugs with novel mechanisms of action. Curr. Med. Chem., 2008, 15(19), 1956-1967.
6. Ma, Z.; Ginsberg, A. M.; Spigelman, M. In: Comprehensive Medicinal Chemistry II; Taylor, J. B.; Triggle, D. J., Eds.; Elsevier: Oxford, 2006, Vol. 7, pp. 699-705.
7. Ginsberg, A. M.; Laurenzi, M. W.; Rouse, D. J.; Whitney, K. D.; Spigelman, M. K. Safety, tolerability, and pharmacokinetics of PA-824 in healthy subjects. Antimicrob. Agents Chemother., 2009, 53(9), 3720-3725.
8. Stover, C. K.; Warrener, P.; Van Devanter, D. R.; Sherman, D. R.; Arain, T. M.; Langhorne, M. H.; Anderson, S. W.; Towell, J. A.; Yuan, Y.; McMurray, D. N.; Kreiswirth, B. N.; Barry, C. E.; Baker, W. R. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature, 2000, 405(6789), 962-966.
9. Li, X.; Manjunatha, U. H.; Goodwin, M. B.; Knox, J. E.; Lipinski, C. A.; Keller, T. H.; Barry, C. E.; Dowd, C. S. Synthesis and antitubercular activity of 7-(R) - and 7-(S)-methyl-2-nitro-6-(S) - (4-(trifluoromethoxy) benzyloxy)-6, 7-dihydro-5H-imidazo[2, 1-b][1, 3]oxazines, analogues of PA-824. Bioorg. Med. Chem. Lett., 2008, 18(7), 2256-2262.
10. Kim, P.; Zhang, L.; Manjunatha, U. H.; Singh, R.; Patel, S.; Jiricek, J.; Keller, T. H.; Boshoff, H. I.; Barry, C. E.; Dowd, C. S. Structureactivity relationships of antitubercular nitroimidazoles. 1. Structural features associated with aerobic and anaerobic activities of 4-and 5-nitroimidazoles. J. Med. Chem., 2009, 52(5), 1317-1328.
11. Kim, P.; Kang, S.; Boshoff, H. I.; Jiricek, J.; Collins, M.; Singh, R.; Manjunatha, U. H.; Niyomrattanakit, P.; Zhang, L.; Goodwin, M.; Dick, T.; Keller, T. H.; Dowd, C. S.; Barry, C. E. Structure-activity relationships of antitubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure-activity relationships. J. Med. Chem., 2009, 52(5), 1329-1344.
12. Thompson, A. M.; Blaser, A.; Anderson, R. F.; Shinde, S. S.; Franzblau, S. G.; Ma, Z.; Denny, W. A.; Palmer, B. D. Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy) benzyl]oxy}-6, 7-dihydro-5H-imidazo[2, 1-b][1, 3]oxazine (PA-824). J. Med. Chem., 2009, 52(3), 637-645.
13. Planche, A.; Scotti, M. T.; García-López, A.; Uriarte, E.; Molina, E.; de Paulo Emerenciano, V. Design of novel antituberculosis compounds using graph-theoretical and substructural approaches. Mol. Divers., 2009, 13(4), 445-458.
14. García-García, A.; Gálvez, J.; de Julián-Ortiz, J. V.; García-Domenech, R.; Muños, C.; Guna, R.; Borrás, R. Search of chemical scaffolds for novel antituberculosis agents. J. Biomol. Screen., 2005, 10(3), 206-214.
15. Palmer, B. D.; Thompson, A. M.; Sutherland, H. S.; Blaser, A.; Kmentova, I.; Franzblau, S. G.; Wan, B.; Wang, Y.; Ma, Z.; Denny, W. A. Synthesis and structure-activity studies of biphenyl analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy) benzyl] oxy}-6, 7-dihydro-5H-imidazo[2, 1-b][1, 3]oxazine (PA-824). J. Med. Chem., 2010, 53(1), 282-294.
16. Cerius2 version 4.8 is a product of Accelrys, Inc., San Diego, USA, http://www.accelrys.com/cerius2.
17. Hansch, C.; Fujita, T. ρ σ π Analysis: A method for the correlation of biological activity and chemical structure. J. Am. Chem. Soc., 1964, 86(1964), 1616-1626.
18. Kubinyi, H. In: Methods and Principles in Medicinal Chemistry; Wolff, M. E., Ed.; VCH: Weinheim, 1993; Vol. 1, pp. 497-522.
19. Roy, P. P.; Roy, K. Classical and 3D-QSAR studies of cytochrome 17 inhibitor imidazole-substituted biphenyls. Molecular Simulation, 2010, 36(4), 311-325.
20. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR. Hydrophobic, Electronic and Steric Constants, American Chemical Society: Washington DC, 1995.
21. Leonard, J. T.; Roy, K. On Selection of Training and Test Sets for the Development of Predictive QSAR models. QSAR Comb. Sci., 2006, 25(3), 235-251.
22. Fan, Y. L.; Shi, M.; Kohn, K. W.; Pommier, Y.; Weinstein, J. N. Quantitative structure-antitumor activity relationships of camptothecin analogues: cluster analysis and genetic algorithm-based studies. J. Med. Chem., 2001, 44(20), 3254-3263.
23. Rogers, D.; Hopfinger, A. J. Application of genetic function approximation to quantitative structure-activity relationships and quantitative-property relationships. J. Chem. Inf. Comput. Sci., 1994, 34(4), 854-866.
24. Snedecor, G. W.; Cochran, W. G. Statistical Methods, Oxford & IBH Publishing Co. Pvt. Ltd.: New Delhi, 1967.
25. Wold, S.; Eriksson, L. In: Chemometric Methods in Molecular Design; van deWaterbeemd, H., Ed.; VCH: Weinheim, 1995, pp. 312-317.
26. Debnath, A. K. In: Combinatorial library design and evaluation: Principles, software tools, and applications in drug discovery; Ghose, A. K.; Viswanadhan, V. N. Eds., Marcel Dekker: New York, 2001, pp. 73-129.
27. Roy, K. On some aspects of validation of predictive QSAR models. Expert Opin. Drug Discov., 2007, 2(12), 1567-1577.
28. Roy, P. P.; Roy, K. On some aspects of variable selection for partial least squares regression models. QSAR Comb. Sci., 2008, 27(3), 302-313.
29. Roy, K.; Roy, P. P. Comparative QSAR studies of CYP1A2 inhibitor flavonoids using 2D and 3D descriptors. Chem. Biol. Drug Des., 2008, 72, 370-382.
30. Roy, P. P.; Paul, S.; Mitra, I.; Roy, K. On Two Novel Parameters for Validation of Predictive QSAR Models. Molecules, 2009, 14(5), 1660-1701.
31. Roy, K.; Paul, S. Docking and 3D QSAR studies of protoporphyrinogen oxidase inhibitor 3H-pyrazolo[3, 4-d][1, 2, 3]triazin-4-one derivatives. J. Mol. Model., 2010, 16(1), 137-153.
32. Eriksson, L.; Jaworska, J.; Worth, A. P.; Cronin, M. T.; McDowell, R. M.; Gramatica, P. Methods for reliability and uncertainty assessment and for applicability evaluations of classification-and regressionbased QSARs. Environ. Health Perspect, 2003, 111(10), 1361-1375.
33. Barry, C. E.; Crick, D. C.; McNeil, M. R. Targeting the formation of the cell wall core of M. tuberculosis. Infect. Disord. Drug Targets, 2007, 7(2), 182-202.