Novel camphane-based anti-tuberculosis agents with nanomolar activity

European Journal of Medicinal Chemistry

Volumn 70, Issue , 2013, Pages 372-379

  Stavrakov, Georgi ^a   Valcheva, Violeta ^b   Philipova, Irena ^c   Doytchinova, Irini ^a  

^a MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^b INSTITUTE OF MICROBIOLOGY   (Bulgaria)

^c BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

Author keywords

Antimycobacterial activity; Camphane; M. tuberculosis H37Rv; MDR; QSAR

Indexed keywords

1 ETHYL 3 ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO [2.2.1]HEPTAN 2 YL)UREA; 2 ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YLCARBAMOYL)PHENYL ACETATE; 2 HYDROXY N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 2 PHENYLACETAMIDE; 2 HYDROXY N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 METHYLBUTANAMIDE; 2 HYDROXY N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PHENYLPROPANAMIDE; 2 HYDROXY N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 4 (METHYLTHIO)BUTANAMIDE; AMIDE; CAMPHENE; ETHAMBUTOL; N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PHENYLPROPANAMIDE; N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) P,P DIPHENYLPHOSPHINIC AMIDE; N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL)CINNAMAMIDE; N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL)FURAN 2 CARBOXAMIDE; N ( 3 HYDROXY 4,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL)NICOTINAMIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; HYDROGEN BOND; IN VITRO STUDY; MOLECULE; MYCOBACTERIUM; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROCESS OPTIMIZATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTIMYCOBACTERIAL ACTIVITY; CAMPHANE; M. TUBERCULOSIS H37RV; MDR; QSAR;

ANTITUBERCULAR AGENTS; BORNANES; DOSE-RESPONSE RELATIONSHIP, DRUG; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84886470777     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.10.015     Document Type: Article

References (31)

1. World Health Organization Global tuberculosis report http://www.who.int/ tb/publications/global-report/en/ 2012
2. Stop TB partnership working group on new TB drugs http://www.stoptb.org/ 2009
3. E.C. Rivers, and R.L. Mancera Drug Discov. Today 13 2008 1090 1098
4. C. Lienhardt, A. Vernon, and M.C. Raviglione Curr. Opin. Pulm. Med. 16 2010 186 193
5. T. Money Nat. Prod. Rep. 2 1985 253 280
6. W. Oppolzer Pure Appl. Chem. 62 1990 1241 1250
7. A. Gorji Trends Pharm. Sci. 24 2003 331 334
8. B.R. Copp, and A.N. Pearce Nat. Prod. Rep. 24 2007 278 297
9. T. Steinbrecher, A. Hrenn, K.L. Dormann, I. Merfort, and A. Labahn Bioorg. Med. Chem. 16 2008 2385 2390
10. R.I. Duclos Jr., D. Lu, J. Guo, and A. Makriyannis Tetrahedron Lett. 49 2008 5587 5589
11. Y. Wang, J. Busch-Petersen, F. Wang, T.J. Kiesow, T.L. Graybill, J. Jin, Z. Yang, J.J. Foley, G.E. Hunsberger, D.B. Schmidt, H.M. Sarau, E.A. Capper-Spudich, Z. Wu, L.S. Fisher, M.S. McQueney, R.A. Rivero, and K.L. Widdowson Bioorg. Med. Chem. Lett. 19 2009 114 118
12. T. Zhou, Q. Shi, C. Chen, L. Huang, P. Ho, S.I. Morris-Natschke, and K. Lee Eur. J. Med. Chem. 47 2012 86 96
13. R.G. Shepherd, C. Baughn, M.L. Cantrall, B. Goodstein, J.P. Thomas, and R.G. Wilkinson Ann. N.Y. Acad. Sci. 135 1966 686 710
14. E.L. Richard, M. Protopopova, E. Crooks, R.A. Slayden, M. Terrot, and C.E. Barry III J. Comb. Chem. 5 2003 172 187
15. H. Häsler, R.P. Kawakami, E. Mlaker, W.B. Severn, and A.E. Stütz Bioorg. Med. Chem. 11 2001 1679 1681
16. A. García-García, J. Gálvez, J. De Julián-Ortiz, R. García-Domenech, C. Muñoz, R. Guna, and R.J. Borráz Biomol. Screen 10 2005 206 214
17. R.E. Lee, M. Protopopova, E. Crooks, R.A. Slayden, M. Terrot, and C.E. Barry III J. Comb. Chem. 5 2003 172 187
18. L. Jia, J.E. Tomaszewski, C. Hanrahan, L. Coward, P. Noker, G. Gorman, B. Nikonenko, and M. Protopopova Br. J. Pharmacol. 144 2005 80 87
19. E. Bogatcheva, C. Hanrahan, B. Nikonenko, R. Samala, P. Chen, J. Gearhart, F. Barbosa, L. Einck, C.A. Nacy, and M. Protopopova J. Med. Chem. 49 2006 3045 3048
20. Y.K. Chen, S. Jeon, P.J. Walsh, and W.A. Nugent Org. Synth. 82 2005 87 92
21. P. Brewster, F. Hiron, E.D. Hughes, C.K. Ingold, and P.A.D.S. Rao Nature 166 1950 179 180
22. L.B. Kier, and L.H. Hall J. Chem. Inf. Comput. Sci. 40 2000 792 795
23. G. Canetti, N. Rist, and J. Grosset Rev. Tuberc. Pneumol. 27 1963 217 272
24. G. Canetti, S. Froman, J. Grosset, P. Hauduroy, M. Langerova, H.T. Mahler, G. Meissner, D.A. Mitchison, and L. Sula Micobacteria: laboratory methods for testing drug sensitivity and resistance Bull. WHO 29 1963 565 578
25. G. Canetti, W. Fox, A. Khomenko, H.T. Mahler, N.K. Menon, D.A. Mitchinson, N. Rist, and N.A. Smelev Bull. Org. Mond. Sante 41 1969 21 43
26. L. Heifets Conventional methods for antimicrobial susceptibility testing of Mycobacterium tuberculosis I. Bastian, F. Portaels, Multidrug-resistant Tuberculosis 2000 Kluwer Academic Publishers Dordrecht, The Netherlands
27. CellTiter 96 Non-Radioactive Cell Proliferation Assay, Technical Bulletin #TB112, Promega Corporation USA, Revised 12/99.
28. L.H. Hall, and L.B. Kier Molecular connectivity chi indices for database analysis and structure-property modeling J. Devillers, A. Balaban, Topological Indices and Related Descriptors in QSAR and QSPR 1999 Gordon and Breach London, UK
29. L.H. Hall, and L.B. Kier Electrotopological state: structure modeling for QSAR and database analysis J. Devillers, A. Balaban, Topological Indices and Related Descriptors in QSAR and QSPR 1999 Gordon and Breach London, UK
30. R. Leardi, R. Boggia, and M. Terrile J. Chemom. 6 1992 267 281
31. J. Friedman Multivariate Adaptive Regression Splines Technical report No. 102 1988 Laboratory for Computational Statistics, Department of Statistics, Stanford University Stanford, California