The effect of systematic structural modifications on the antibacterial activity of novel oxazolidinones

Medicinal Chemistry

Volumn 7, Issue 1, 2011, Pages 45-55

  Pintér, Gábor ^a   Bereczki, Ilona ^a   Roth, Elizabeth ^a   Sipos, Attila ^a   Varghese, Reny ^b   Udo, Edet Ekpenyong ^b   Ostorházi, Eszter ^c   Rozgonyi, Ferenc ^c   Phillips, Oludotun Adebayo ^b   Herczegh, Pál ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b KUWAIT UNIVERSITY   (Kuwait)

^c SEMMELWEIS UNIVERSITY   (Hungary)

Author keywords

'Click' reaction; Antibacterial agents; Linezolid; Oxazolidinone; Squaramide; Tetraethylene glycol (TEG)

Indexed keywords

4 TETRAETHYLENEGLYCOL TRIAZOLYL DERIVATIVE; NUCLEOSIDE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; GLYCOLS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; OXAZOLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 78751639507     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340611794072670     Document Type: Article

References (35)

1. Shinabarger, D.L.; Marotti, K.R.; Murray, R.W.; Lin, A.H.; Melchior, E.P.; Swaney, S.M.; Dunyak, D.S.; Demyan, W.F.; Buysse, J.M. Mechanism of action of oxazolidinones: effects of linezolid and eperezolid on translation reactions. Antimicrob. Agents Chemother., 1997, 41, 2132-2136.
2. French, G. Linezolid. Int. J. Clin. Pract., 2001, 55, 59-63.
3. Hutchinson, D.K. Oxazolidinone antibacterial agents: a critical review. Curr. Top. Med. Chem., 2003, 3, 1021-1042.
4. Gravestock, M.B. Recent developments in the discovery of novel oxazolidinone antibacterials. Curr. Opin. Drug Discov. Devel., 2005, 8, 469-477.
5. Prasad, J.V.N.V. New oxazolidinones. Curr. Opin. Microbiol., 2007, 10, 454-460.
6. Poce, G.; Zappia G.; Porretta G.C.; Botta B.; Biava M. New oxazolidinone derivatives as antibacterial agents with improved activity. Expert Opin. Ther. Pat., 2008, 18, 97-121.
7. Phillips O.A.; Udo E.E.; Ali A.A.M.; Al-Hassawi N. Synthesis and antibacterial activity of 5-substituted oxazolidinones. Bioorg. Med. Chem., 2003, 11, 35-41.
8. Phillips, O.A.; Udo E.E.; Ali A.A.M.; Samuel S.M. Synthesis and antibacterial activity of new N-linked 5-triazolylmethyl oxazolidinones. Bioorg. Med. Chem., 2005, 13, 4113-4123.
9. Phillips, O.A.; Udo, E.E.; Ali, A.A.M.; Samuel S.M. Structure- antibacterial activity of arylcarbonyl- and arylsulfonyl-piperazine 5-triazolylmethyl oxazolidinones. Eur. Med. Chem., 2007, 42, 214-225.
10. Leach, K.L.; Swaney, S.M.; Colca, J.R.; McDonald, W.G.; Blinn, J.R.; Thomasco, L.M.; Gadwood, R.C.; Shinabarger, D.L.; Xiong, L.; Mankin, A.S. The site of action of oxazolidinone antibiotics in living bacteria and in human mitochondria. Mol. Cell., 2007, 26, 393-402.
11. Ippolito, J.A.; Kanyo, Z.F.; Wang, D.; Franceschi, F.J.; Moore, P.B.; Steitz, T.A.; Duffy, E.M. Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50S ribosomal subunit. J. Med. Chem., 2008, 51, 3353-3356.
12. Franceschi, F.; Duffy, E.M. Structure-based drug design meets the ribosome. Biochem. Pharmacol., 2006, 71, 1016-1025.
13. Cohen, S.; Lacher, J.R.; Park, J.D. Diketocyclobutenediol. J. Am. Chem. Soc., 1959, 81, 3480;
14. Park, J.D.; Cohen, S.; Lacher, J.R. Hydrolysis reactions of halogenated cyclobutene ethers: synthesis of diketocyclobutenediol. J. Am. Chem. Soc., 1962, 84, 2919;
15. Cohen, S.; Cohen, S.G. Preparation and reactions of derivatives of squaric acid. Alkoxy-, hydroxy-, and aminocyclobutenediones. J. Am. Chem. Soc., 1966, 88, 1533.
16. Genin, M.J.; Allwine, D.A.; Anderson, D.J.; Barbachyn, M.R.; Emmert, D.E.; Garmon, S.A.; Graber, D.R.; Grega, K.C.; Hester, J.B.; Hutchinson, D.K.; Morris, J.; Reischer, R.J.; Ford, C.W.; Zurenko, G.E.; Hamel, J.C.; Schaadt, R.D.; Stapert, D.; Yagi, B.H. Substituent effects on the antibacterial activity of nitrogen-carbonlinked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms. Haemophilus influenzae and Moraxella catarrhalis. J. Med. Chem., 2000, 43, 953-970.
17. 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.; Zurenko, G.E. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrugresistant gram-positive bacterial infections. J. Med. Chem., 1996, 39, 673-679.
18. Bock, V.D.; Hiemstra, H.; van Maarseveen, J.H. Cu(I)-Catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem., 2006, 51-68.
19. Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C.J.; Hales, N.J.; Ramsay, R.R.; Gravestock, M.B. Identification of 4- substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A. J. Med. Chem., 2005, 48, 499-506.
20. Binder, W.H.; Kluger, C. Azide/alkyne "click" reactions: Applications in material science and organic synthesis. Curr. Org. Chem., 2006, 10, 1791-1815.
21. Tietze, L.F.; Arlt, M.; Beller, M.; Glüsenkamp, K.H.; Jahde, E.; Rajewsky, M.G. Anticancer agents, 15. Squaric acid diethyl ester: A new coupling reagent for the formation of drug biopolymer conjugates. Synthesis of squaric acid ester amides and diamides. Chem. Ber., 1991, 124, 1215-1223.
22. Aronhime, J.; Koltai, T.; Braude, V.; Fine, S.; Niddam, T. Preparation of solid forms of linezolid PCT WO 2006110155 A1 20061019, 2006. CA No. 2006:426029.
23. Yamamoto, I.; Sekine, M.; Hata, T. One-step synthesis of 5'-azidonucleosides. J. Chem. Soc., Perkin Trans., 1980, 1, 306-310.
24. Winans, K.A.; Bertozzi, C.R. An inhibitor of the human UDPGlcNAc 4-epimerase identified from a uridine-based library. Chem. Biol., 2002, 9, 113-129.
25. Dean, D.K. An Improved synthesis of 5'-amino-5'-deoxyguanosine. Synth. Commun., 2002, 32, 1517-1521.
26. Hutchinson, D.K.; Brickner, S.J.; Barbachyn, M.R.; Gammill, R B. Oxazolidinones antibiotics containing a substituted diazine moiety. PCT WO99323384, 1993. CA No. 1994:323599;
27. Takhi, M.; Singh, G.; Murugan, C.; Thaplyyal, N.; Maitra, S.; Bhaskarreddy, K.M.; Amarnath, P.V.; Mallik, A.; Harisudan, T.; Trivedi, R.K.; Sreenivas, K.; Selvakumar, N.; Iqbal, J. Novel and potent oxazolidinone antibacterials featuring 3-indolylglyoxamide substituents. Bioorg. Med. Chem. Lett., 2008, 18, 5150-5155.
28. Phillips O.A.; Udo E.E.; Abdel-Hamid M.A.; Varghese R. Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3- triazole) methyl oxazolidinones. Eur. J. Med. Chem., 2009, 44, 3217-3227.
29. Symyx Technologies, Inc. 2440 Camino Ramon, Suite 300 San Ramon, CA 94583.
30. Bérubé, G. Natural and synthetic biologically active dimeric molecules: anticancer agents, anti-HIV agents, steroid derivatives and opioid antagonists. Curr. Med. Chem., 2006, 13, 131-154.
31. Kerns, R.J.; Rybak, M.J.; Kaatz, G.W.; Vaka, F.; Cha, R.; Grucz, R.G.; Diwadkar, V.U.; Ward, T.D. Piperazinyl-linked fluoroquinolone dimers possessing potent antibacterial activity against drugresistant strains of Staphylococcus aureus. Bioorg. Med. Chem. Lett., 2003, 13, 1745-1749. (Pubitemid 36561156)
32. Barbachyn, M.R.; Ford, C.W. Oxazolidinone structure-activity relationships leading to linezolid. Angew. Chem., Int. Ed., 2003, 42, 2010-2023.
33. 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.; Zurenko, G.E. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant grampositive bacterial infections. J. Med. Chem., 1996, 39, 673-679.
34. Meyers, S.R.; Juhn, F. S.; Griset, A. P.; Luman, N.R.; Grinstaff, M. W. Anionic amphiphilic dendrimers as antibacterial agents. J. Am. Chem. Soc., 2008, 130, 14444-14445.
35. Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Susceptibility Testing. 20th Informational Supplement M100 - S20. CLSI, Wayne, PA USA, 2010.