Novel and potent oxazolidinone antibacterials featuring 3-indolylglyoxamide substituents

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 18, 2008, Pages 5150-5155

  Takhi, Mohamed ^a   Singh, Gurpreet ^a   Murugan, C ^a   Thaplyyal, Nirvesh ^a   Maitra, Soma ^a   Bhaskarreddy, K M ^a   Amarnath, P V S ^a   Mallik, Arundhuti ^a   Harisudan, T ^a   Trivedi, Ravi Kumar ^a   Sreenivas, K ^a   Selvakumar, N ^a   Iqbal, Javed ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Antibacterials; Indole; Linezolid; Oxazolidinones

Indexed keywords

3 INDOLYLGLYOXAMIDE; AMIDE; ANTIINFECTIVE AGENT; EPEREZOLID; LINEZOLID; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; AREA UNDER THE CURVE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG ELIMINATION; DRUG HALF LIFE; DRUG POTENCY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; INFECTION; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ACETAMIDES; ANIMALS; ANTI-BACTERIAL AGENTS; DISEASE MODELS, ANIMAL; ENTEROCOCCUS FAECALIS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HAEMOPHILUS INFLUENZAE; INDOLES; METHICILLIN RESISTANCE; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; OXAZOLIDINONES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; VANCOMYCIN RESISTANCE;

NEGIBACTERIA; POSIBACTERIA;

EID: 51349148303     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.03.043     Document Type: Article

References (34)

1. Clemett D., and Markham A. Drug 59 (2000) 815
2. Shinabarger D.L., Marotti K.R., Murray R.W., Lin A.H., Melchoir E.P., Swaney S.M., Dunyak D.S., Demyan W.F., and Buysse J.M. Antimicrob. Agents Chemother. 41 (1997) 2132P
3. Kloss P., Xiong L., Mankin A.S., Shinabarger D.L., and Mankin A.S. J. Mol. Biol. 294 (1999) 93
4. Tsirodas S., Gold H.S., Sakoulas G., Eliopoulas G.M., Wennerstein C., Venkataraman L., Moellering Jr. R.C., and Ferro M.J. Lancet 358 (2001) 207
5. Johnson A.P., Tysall L., Stockdale M.W., Woodford N., Kaufmann M.E., Warner M., Livermoore D.M., Asboth F., and Alleberger F.J. Eur. J. Clin. Microbial. Infect. Dis. 21 (2002) 751
6. Jo Y.W., Im W.B., Rhee J.K., Shim M.J., Kim W.B., and Choi E.C. Bioorg. Med. Chem. 12 (2004) 5909
7. Renslo A.R., Atuegbu A., Herradura P., Jaishankar P., Ji M., Leach K.L., Huband M.D., Dermyer M.R., Wu L., Prasad J.V.V.N.V., and Gordeev M.F. Bioorg. Med. Chem. Lett. 17 (2007) 5036
8. Griera R., Llopart C.C., Amat M., Bosch J., Castilo J.C.D., and Huguet J. Bioorg. Med. Chem. Lett. 15 (2005) 2515
9. Renslo A.R., Luehr G.W., and Gordeev M.F. Bioorg. Med. Chem. 14 (2006) 4227 and references cited there in
10. Takhi M., Murugan C., Munikumar M., Bhaskarreddy K.M., Singh G., Sreenivas K., Sitaramkumar M., Selvakumar N., Das J., Trehan S., and Iqbal J. Bioorg. Med. Chem. Lett. 16 (2006) 2391
11. Selvakumar N., Srinivas D., Khera M.K., Kumar M.S., Mamidi R.N.V.S., Sarnaik H., Charavaryamath C., Rao B.S., Raheem M.A., Das J., Iqbal J., and Rajagopalan R. J. Med. Chem. 45 (2002) 3953
12. Das J., Rao C.V.L., Sastry T.V.R.S., Roshiah M., Sankar P.G., Khadeer A., Kumar M.S., Mallik A., Selvakumar N., Iqbal J., and Trehan S. Bioorg. Med. Chem. Lett. 15 (2005) 337
13. Selvakumar N., Raheem M.A., Khera M.K., Rajale T.V., Kumar M.S., Kandepu S., Das J., Rajagopalan R., Iqbal J., and Trehan S. Bioorg. Med. Chem. Lett. 13 (2003) 4169
14. Philips O.A., Udo E.E., Ali A.A.M., and Samuel S.M. Eur. J. Med. Chem. 42 (2007) 214
15. Philips O.A., Udo E.E., Ali A.A.M., and Samuel S.M. Bioorg. Med. Chem. 13 (2005) 4113
16. Metha, A.; Arora, S. K.; Das, B.; Ray, A.; Rudra, S. Indian Patent 827/DEL, 2001.
17. Hutchinson, D. K.; Brickner, S. J.; Barbachyn, M. R.; Gammill, R. B. PCT WO199323384, 1993.
18. -1; MS: (m/z) 508 (M+1).
19. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard, 5th ed.; NCCLS: USA, 2000; Vol. 20, No. 2, pp M7-A5.
20. Tokuyama R., Takahashi Y., Tomita Y., Tsubochi M., Yoshida T., Iwasaki N., Kado N., Okezaki E., and Nagata O. Chem. Pharm. Bull. 49 (2001) 353
21. Tokuyama R., Takahashi Y., Tomita Y., Tsubochi M., Iwasaki N., Kado N., Okezaki E., and Nagata O. Chem. Pharm. Bull. 49 (2001) 361
22. Tokuyama R., Takahashi Y., Tomita Y., Suzuki T., Yoshida T., Iwasaki N., Kado N., Okezaki E., and Nagata O. Chem. Pharm. Bull. 49 (2001) 347
23. 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
24. Lee C.S., Allwine D.A., Barbachyn M.R., Grega K.C., Dolak L.A., Ford C.W., Jensen R.M., Seest E.P., Hamel J.C., Schaadt R.D., Stapert D., Yagi B.H., Zurenko G.E., and Genin M.J. Bioorg. Med. Chem. 9 (2001) 3243
25. Dixit P.P., Nair P.S., Patil V.J., Jain S., Arora S.K., and Sinha N. Bioorg. Med. Chem. Lett. 15 (2005) 3002
26. Ciske F.L., Barbachyn M., Genin M.J., Grega K.C., Lee C.S., Dolak L.A., Seest E.P., Watt W., Adams W.J., Friis J.M., Ford C.W., and Zurenko G.E. Bioorg. Med. Chem. Lett. 13 (2003) 4235
27. Renslo A.R., Luehr G.W., Lam S., Westlund N.E., Gomez M., Hackbarth C.J., Patel D.V., and Gordeev M.F. Bioorg. Med. Chem. Lett. 16 (2006) 3475
28. Gordeev, M. F.; Renslo, A.; Luehr, G. W.; Lam, S.; Westlund, N. E.; Patel, D. V. U.S. Patent 6,884,813, 2005.
29. 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
30. Fan H., Xu G., Chen Y., Jiang Z., Zhang S., Yang Y., and Ji R. Eur. J. Med. Chem. 42 (2007) 1137
31. Gravestock M.B., Acton D.G., Betts M.J., Dennis M., Hatter G., McGregor A., Swain M.L., Wilson R.G., Woods L., and Wookey A. Bioorg. Med. Chem. Lett. 13 (2003) 4179
32. Carsenti-Dellamonica H., Galimand M., Vandenbos F., Pradier C., Roger P.M., Dunais B., Sabah M., Mancini G., and Dellamonica P. J. Antimicrob. Chemother. 56 (2005) 633
33. Webber M.A., and Piddock L.J.V. J. Antimicrob. Chemother. 51 (2003) 9
34. 50 values were calculated by Probit analysis.