Antibacterial activity of pyrrolopyridine-substituted oxazolidinones: synthesis and in vitro SAR of various C-5 acetamide replacements

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 17, 2006, Pages 4537-4542

  Paget, Steven D ^a   Boggs, Christine M ^a   Foleno, Barbara D ^a   Goldschmidt, Raul M ^a   Hlasta, Dennis J ^a   Weidner Wells, Michele A ^a   Werblood, Harvey M ^a   Bush, Karen ^a   Macielag, Mark J ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Antibacterial agents; C 5 acetamide isosteres; Methicillin resistant Staphylococcus aureus; Pyrrolopyridine substituted oxazolidinones; Vancomycin resistant Enterococcus faecium

Indexed keywords

ACETAMIDE DERIVATIVE; ANTIINFECTIVE AGENT; LINEZOLID; OXAZOLIDINONE DERIVATIVE; PYRIDINE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; GRAM POSITIVE BACTERIUM; NONHUMAN; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ACETAMIDES; ANTI-BACTERIAL AGENTS; ENTEROCOCCUS; MOLECULAR STRUCTURE; OXAZOLIDINONES; PYRIDINES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

POSIBACTERIA;

EID: 33746233275     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.06.023     Document Type: Article

References (26)

1. Mutnick A.H., Biedenbach D.J., Turnidge J.D., and Jones R.N. Diagn. Microbiol. Infect. Dis. 43 (2002) 65
2. Linden P.K. Drugs 62 (2002) 425
3. Miller D., Urdaneta V., Weltman A., and Park S. Morb. Mortal. Wkly. Rep. 51 (2002) 902
4. Jacoby, G.; Bush, K. In Frontiers in Antimicrobial Resistance: a Tribute to Stuart B. Levy; White, D. G., Alekshun, M. N., McDermott, P. F., Eds.; ASM Press: Washington, DC, 2005; Chapter 5, pp 53-65.
5. Paget S.D., Foleno B.D., Boggs C.M., Goldschmidt R.M., Hlasta D.J., Weidner-Wells M.A., Werblood H.M., Wira E., Bush K., and Macielag M. Bioorg. Med. Chem. Lett. 13 (2003) 4173
6. Paget, S.; Boggs, C.; Foleno, B.; Goldschmidt, R.; Hilliard, J.; Melton, J.; Stryker, S.; Wira, E.; Bush, K.; Macielag, M. 42nd Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego, CA, 2002; F-1318.
7. Paget, S.; Hlasta, D. WO 01/42242 A, 2001.
8. Paget, S.; Boggs, C.; Foleno, B.; Goldschmidt, R.; Grant, E.; Hilliard, J.; Hlasta, D.; Weidner-Wells, M.; Werblood, H.; Wira, E.; Bush, K.; Macielag, M. 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago, IL, 2001; F-1048.
9. Foleno, B. D.; Goldschmidt, R.; Licata, L.; Montenegro, D.; Paget, S.; Weidner-Wells, M.; Wira, E.; Macielag, M.; Bush, K. 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago, IL, 2001; F-1049.
10. Hilliard, J.; Goldschmidt, R.; Fernandez, J.; Melton, J.; Paget, S.; Weidner-Wells, M.; Macielag, M.; Bush, K. 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago, IL, 2001; F-1050.
11. Gregory W.A., Brittelli D.R., Wang C.-L.J., Wuonola M.A., McRipley R.J., Eustice D.C., Eberly V.S., Bartholomew P.T., Slee A.M., and Forbes M. J. Med. Chem. 32 (1989) 1673
12. Singh U., Raju B., Lam S., Zhou J., Gadwood R.C., Ford C.W., Zurenko G.E., Schaadt R.D., Morin S.E., Adams W.J., Friis J.M., Courtney M., Palandra J., Hackbarth C.J., Lopez S., Wu C., Mortell K.H., Trias J., Yuan Z., Patel D.V., and Gordeev M.F. Bioorg. Med. Chem. Lett. 13 (2003) 4209
13. Gravestock, M. B. WO 99/64417 A2, 1999.
14. Gravestock M.B., Acton D.G., Betts M.J., Dennis M., Hatter G., McGregor A., Swain M.L., Wilson G.R., Woods L., and Wookey A. Bioorg. Med. Chem. Lett. 13 (2003) 4179
15. Reck F., Zhou F., Girardot M., Kern G., Eyermann C.J., Hales N.J., Ramsay R.R., and Gravestock M.B. J. Med. Chem. 48 (2005) 499
16. Hlasta, D. J. WO 01/42229 A1, 2001.
17. Petersen, U.; Krebs, A.; Schenke, T.; Grohe, K.; Bremm, K.-D.; Endermann, R.; Metzger, K.-G.; Zeiler, H.-J. US 94/5371090, 1994, CAN 119:49377.
18. Brickner S.J., Hutchinson D.K., Barbachyn M.R., Manninen P.R., Ulanowicz D.A., Garmon S.A., Grega K.C., Hendges S.K., Toops D.S., Ford C.W., and Zurenko G.E. J. Med. Chem. 39 (1996) 673
19. Lwowski W. Synthesis 5 (1971) 263
20. Wittenbrook L.S. J. Heterocycl. Chem. 12 (1975) 37
21. Ohta A., Aoyagi Y., Kurihara Y., Yuasa K., Shimazaki M., Kurihara T., and Miyamae H. Heterocycles 26 (1987) 3181
22. National Committee for Clinical Laboratory Standards: Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 5th ed. Approved standard: NCCLS Document M7-A5, 2000.
23. 1H NMR and MS. Purity of tested compounds was ≥95%.
24. Wookey A., Turner P.J., Greenhalgh J.M., Eastwood M., Clarke J., and Sefton C. Clin. Microbiol. Infect. 10 (2004) 247
25. Jang S.-Y., Ha Y.H., Ko S.W., Lee W., Lee J., Kim S., Kim Y.W., Lee W.K., and Ha H.-J. Bioorg. Med. Chem. Lett. 14 (2004) 3881
26. Ogawa H., Aoyama T., and Shioiri T. Heterocycles 42 (1996) 75