Library of 1,4-disubstituted 1,2,3-triazole analogs of oxazolidinone RNA-binding agents

Journal of Combinatorial Chemistry

Volumn 12, Issue 4, 2010, Pages 491-496

  Acquaah Harrison, George ^a   Zhou, Shu ^a   Hines, Jennifer V ^a   Bergmeier, Stephen C ^a  

^a OHIO UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BACTERIAL RNA; OXAZOLIDINONE DERIVATIVE; TRIAZOLE DERIVATIVE; MOLECULAR LIBRARY;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG DESIGN; DRUG EFFECT; GRAM POSITIVE BACTERIUM; MOLECULAR LIBRARY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY; DRUG EFFECTS;

ANTI-BACTERIAL AGENTS; BINDING SITES; COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; GRAM-POSITIVE BACTERIA; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXAZOLIDINONES; RNA, BACTERIAL; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; TRIAZOLES;

EID: 77954548244     PISSN: 15204766     EISSN: 15204774     Source Type: Journal    
DOI: 10.1021/cc100029y     Document Type: Article

References (36)

1. Means, J., Katz, S. J., Anupam, R., Nayek, A., Hines, J. V., and Bergmeier, S. C. Bioorg. Med. Chem. Lett. 2006, 16, 3600-3604
2. Grundy, F. J., Rollins, S. M., and Henkin, T. M. J. Bacteriol. 1994, 176, 4518-4526
3. Gutierrez-Preciado, A., Henkin, T. M., Grundy, F. J., Yanofsky, C., and Merino, E. Microbiol. Mol. Biol. Rev. 2009, 36-61
4. Anupam, R., Nayek, A., Green, N. J., Grundy, F. J., Henkin, T. M., Means, J. A., Bergmeier, S. C., and Hines, J. V. Bioorg. Med. Chem. Lett. 2008, 18, 3541-3544
5. Hutchinson, D. K. Curr. Top. Med. Chem. 2003, 3, 1021-1042
6. Snyder, L. B., Meng, Z., R., M., D'Andrea, S. V., Marinier, A., Quesnelle, C. A., Gill, P., DenBleyker, K. L., Fung-Tomc, J. C., Frosco, M., Martel, A., Barrett, J. F., and Bronson, J. J. Bioorg. Med. Chem. Lett. 2004, 14, 4735-4739
7. Barbachyn, M. R., Cleek, G. J., Dolak, L. A., Garmon, S. A., Morris, J., Seest, E. P., Thomas, R. C., Toops, D. S., Watt, W., Wishka, D. G., Ford, C. W., Zurenko, G. E., Hamel, J. C., Schaadt, R. D., Stapert, D., Yagi, B. H., Adams, W. J., Friis, J. M., Slatter, J. G., Sams, J. P., Oien, N. L., Zaya, M. J., Wienkers, L. C., and Wynalda, M. A. J. Med. Chem. 2003, 46, 284-302
8. Tron, G. C., Pirali, T., Billington, R. A., Canonico, P. L., Sorba, G., and Genazzani, A. A. Med. Res. Rev. 2008, 28, 278-308
9. Brik, A., Alexandratos, J., Lin, Y.-C., Elder, J. H., Olson, A. J., Wlodawer, A., Goodsell, D. S., and Wong, C.-H. ChemBioChem 2005, 6, 1167-1169
10. Molecular modeling was performed with Spartan'08 for Macintosh, Wavefunction Inc., Irvine, CA. The lowest energy conformer for each compound was obtained using molecular mechanics MMFF base set.
11. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; p 1 - 176.
12. Huisgen, R., Knorr, R., Moebius, L., and Szeimies, G. Chem. Ber. 1965, 98, 4014-4021
13. Tornøe, C. W., Christensen, C., and Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
14. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
15. Moses, J. E. and Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262
16. Bock, V. D., Hiemstra, H., and van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68
17. Kolb, H. C. and Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137
18. Kolb, H. C., Finn, M. G., and Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
19. Scriven, E. and Turnbull, K. Chem. Rev. 1988, 88, 297-398
20. Stamatov, S. D. and Stawinski, J. Tetrahedron 2005, 61, 3659-3669
21. Sabitha, G., Babu, R. S., Rajkumar, M., and Yadav, J. S. Org. Lett. 2002, 4, 343-345
22. Onaka, M., Sugita, K., and Izumi, Y. J. Org. Chem. 1989, 54, 1116-1123
23. Kiasat, A. R. and Kazemi, F. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2387-2392
24. Boruwa, J., Borah, J. C., Kalita, B., and Barua, N. C. Tetrahedron Lett. 2004, 45, 7355-7358
25. Langlois, N. and Moro, A. Eur. J. Org. Chem. 1999, 3483-3488
26. Lambert, S. J., Kabalka, G. W., Knapp, F. F., Jr., and Srivastava, P. C. J. Org. Chem. 1991, 56, 3707-3711
27. Verron, J., Malherbe, P., Prinssen, E., Thomas, A. W., Nock, N., and Masciadri, R. Tetrahedron Lett. 2007, 48, 377-380
28. Chittaboina, S., Xie, F., and Wang, Q. Tetrahedron Lett. 2005, 46, 2331-2336
29. Yan, Z.-Y., Zhao, Y.-B., Fan, M.-J., Liu, W.-M., and Liang, Y.-M. Tetrahedron 2005, 61, 9331-9337
30. Kaval, N., Ermolat'ev, D., Appukkuttan, R., Dehaen, W., Kappe, C. O., and Van der Eycken, E. J. Comb. Chem. 2005, 7, 490-502
31. Collin, M.-P., Hobbie, S. N., Bottger, E. C., and Vasella, A. Helv. Chim. Acta 2008, 91, 1838-1848
32. Smith, N. M., Greaves, M. J., Jewell, R., Perry, M. W. D., Stocks, M. J., and Stonehouse, J. P. Synlett 2009, 1391-1394
33. Luesse, S. B., Wells, G., Nayek, A., Smith, A. E., Kusche, B. R., Bergmeier, S. C., McMills, M. C., Priestley, N. D., and Wright, D. L. Bioorg. Med. Chem. Lett. 2008, 18, 3946-3949
34. Gerdeman, M. S., Henkin, T. M., and Hines, J. V. Nucleic Acids Res. 2002, 30, 1065-1072
35. Means, J. A. and Hines, J. V. Bioorg. Med. Chem. Lett. 2005, 15, 2169-2172
36. A tabular listing of the fluoresence data used to generate Figure 6 can be found in the Supporting Information.