Synthesis and biological evaluation of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives

European Journal of Medicinal Chemistry

Volumn 106, Issue , 2015, Pages 120-131

  Phillips, Oludotun A ^a   D'Silva, Roselyn ^a   Bahta, Teklu O ^b   Sharaf, Leyla H ^a   Udo, Edet E ^a   Benov, Ludmil ^a   Eric Walters, D ^b  

^a KUWAIT UNIVERSITY   (Kuwait)

^b ROSALIND FRANKLIN UNIVERSITY OF MEDICINE AND SCIENCE   (United States)

Author keywords

(N Hydroxyalkanamido)methyloxazolidinones; Antibacterial activity; Gram negative bacteria; Gram positive bacteria; Hydroxamic acid oxazolidinones; Monoamine oxidases inhibition

Indexed keywords

5 (HYDROXAMIC ACID)METHYL OXAZOLIDINONE DERIVATIVE; ANTIBIOTIC AGENT; CLORGYLINE; HYDROXAMIC ACID; LINEZOLID; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; N [[3 (3 FLUORO 4 MORPHOLINOPHENYL) 2 OXOXAZOLIDIN 5YL]METHYL] N HYDROXY ISOBUTYRAMIDE; N [[3 (3 FLUORO 4 MORPHOLINOPHENYL) 2 OXOXAZOLIDIN 5YL]METHYL] N HYDROXY PROPIONAMIDE; N [[3 (3 FLUORO 4 MORPHOLINOPHENYL) 2 OXOXAZOLIDIN 5YL]METHYL] N HYDROXYCYCLOPROPANECARBOXAMIDE; N [[3 [4 (4 ACETYLPIPERAZIN 1 YL) 3 FLUOROPHENYL] 2 OXOOXAZOLIDIN 5 YL]METHYL] N HYDROXYACETAMIDE; N [[3 [4 (4 ACETYLPIPERAZIN 1 YL) 3 FLUOROPHENYL] 2 OXOOXAZOLIDIN 5 YL]METHYL] N HYDROXYCYCLOPROPANECARBOXAMIDE; N [[3 [4 (4 ACETYLPIPERAZIN 1 YL) 3 FLUOROPHENYL] 2 OXOOXAZOLIDIN 5 YL]METHYL] N HYDROXYISOBUTYRAMIDE; N [[3 [4 (4 ACETYLPIPERAZIN 1 YL) 3 FLUOROPHENYL] 2 OXOOXAZOLIDIN 5 YL]METHYL] N HYDROXYPROPRIONAMIDE; OXAZOLIDINONE DERIVATIVE; PARGYLINE; UNCLASSIFIED DRUG; AMINE OXIDASE (FLAVIN CONTAINING); MONOAMINE OXIDASE INHIBITOR;

ANTIBACTERIAL ACTIVITY; ARTICLE; BINDING SITE; COMPUTER MODEL; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; IC50; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; HYDROXAMIC ACIDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; OXAZOLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84947264564     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.10.025     Document Type: Article

References (32)

1. H. Suzuki, I. Utsunomiya, K. Shudo, N. Fukuhara, T. Iwaki, T. Yasukata, Antibacterial oxazolidinone analogues having a N-hydroxyacetyl-substituted seven-membered [1, 2, 5] triazepane or [1, 2, 5]oxadiazepane C-ring unit, Eur. J. Med. Chem. 63 (2013) 811-825.
2. H. Suzuki, I. Utsunomiya, K. Shudo, N. Fukuhara, T. Iwaki, T. Yasukata, Synthesis and in vitro/in vivo antibacterial activity of oxazolidinones having thiocarbamate at C-5 on the A-ring and an amide-or urea-substituted [1, 2, 5] triazepane or [1, 2, 5]oxadiazepane as the C-ring, Eur. J. Med. Chem. 69 (2013) 262-277.
3. N.M. Clark, E. Hershberger, M.J. Zervosc, J.P. Lynch III, Antimicrobial resistance among gram-positive organisms in the intensive care unit, Curr. Opin. Crit. Care 9 (2003) 403-412.
4. B.K. Srivastava, R. Soni, J.Z. Patel, M.R. Jain, P.R. Patel, Oxazolidinone antibacterials and our experience, Anti-Infect. Agents Med. Chem. 7 (2008) 258-280.
5. J.B. Locke. J. Finn, M. Hilgers, G. Morales, S. Rahawi, G.C. Kedar, J.J. Picazo, W. Im, K.J. Shaw, J.L. Stein, Structure-Activity relationships of diverse oxazolidinones for linezolid-resistant Staphylococcus aureus strains possessing the cfr methyltransferase gene or ribosomal mutations, Antimicrob. Agents Chemother. 54 (2010) 5337-5343.
6. Sivextro Approval History, June 2014. http://www.drugs.com/history/ sivextro.html (accessed April 2015).
7. D.L. Shinabarger, K.R. Marotti, R.W. Murray, A.H. Lin, E.P. Melchior, S.M. Swaney, D.S. Dunyak, W.F. Demyan, J.M. Buysse, Antimicrob. Agents Chemother. 41 (1997) 2132-2136.
8. S. Ager, K. Gould, Infect. Drug Res. 5 (2012) 87-102.
9. J.A. Ippolito, Z.F. Kanyo, D. Wang, F.J. Franceschi, P.B. Moore, T.A. Steitz, E.M. Duffy. J. Med. Chem. 51 (2008) 3353-3356.
10. K.J. Shaw, M.R. Barbachyn, The oxazolidinones: past, present and future, Ann. N. Y. Acad. Sci. 1241 (2011) 48-70.
11. K.L. Leach, S.J. Brickner, M.C. Noe, P.F. Miller, Linezolid, the first oxazolidinone antibacterial agent, Ann. N. Y. Acad. Sci. 1222 (2011) 49-54.
12. K.R. Lawrence, M. Adra, P.K. Gillman, Serotonin toxicity associated with the use of linezolid: a review of postmarketing data, Clin. Infect. Dis. 42 (2006) 1578-1583.
13. J.V. Meck, D.S. Martin, D.S. D'Aunno, W.W. Waters, Pressor response to intravenous tyramine is a marker of cardiac, but not vascular, adrenergic function. J. Cardiovasc. Pharmacol. 41 (2003) 126-131.
14. S. Flanagan, K. Bartizal, S.L. Minassian, E. Fang, P. Prokocimer, In vitro, in vivo, and clinical studies of tedizolid to assess the potential for peripheral or central monoamine oxidase interactions, Antimicrob. Agents Chemother. 57 (7) (2013) 3060-3306.
15. K. Michalska, I. Karpiuk, M. Kr-ol, S. Tyski, Recent development of potent analogues of oxazolidinone antibacterial agents, Bioorg. Med. Chem. 21 (2013) 577-591.
16. J.B. Locke. J. Finn, M. Hilgers, G. Morales, S. Rahawi, G.C. Kedar, J.J. Picazo, W. Im, K.J. Shaw, J.L. Stein, Structureeactivity relationships of diverse oxazolidinones for linezolid-resistant Staphylococcus aureus strains possessing the cfr methyltransferase gene or ribosomal mutations, Antimicrob. Agents Chemother. 54 (12) (2010) 5337-5343.
17. O.A. Phillips, E.E. Udo, A.A.M. Ali, N. Al-Hassawi, Synthesis and antibacterial activity of 5-substituted oxazolidinones, Bioorg. Med. Chem. 11 (2003) 35-41.
18. O.A. Phillips, E.E. Udo, A.A.M. Ali, S.M. Samuel, Synthesis and antibacterial activity of new N-linked 5-Driazolymethyl oxazolidinones, Bioorg. Med. Chem. 13 (2005) 4113-4123.
19. O.A. Phillips, E.E. Udo, A.A.M. Ali, S.M. Samuel, Structure-Antibacterial activity of arylcarbonyl-And arylsulfonyl-piperazine 5-Driazolylmethyl oxazolidinones, Eur. J. Med. Chem. 42 (2007) 214-225.
20. O.A. Phillips, E.E. Udo, M.E. Abdel-Hamid, R. Varghese, Synthesis and antibacterial activities of N-substituted glycinyl 1H-1, 2, 3-Driazolyl oxazolidinones, Eur. J. Med. Chem. 66 (2013) 246-257.
21. F. Reck, F. Zhou, M. Girardot, G. Kern, C.J. Eyermann, N.J. Hales, R.R. Ramsay, M.B. Gravestock, Identification of 4-substituted 1, 2, 3-Driazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A. J. Med. Chem. 48 (2005) 499-506.
22. T.-J. Poel, R.C. Thomas, W.J. Adams, P.A. Aristoff, M.R. Barbachyn, F.E. Boyer, et al., Antibacterial oxazolidinones possessing a novel C-5 side chain. (5R)-Drans-3-[3-fluoro-4-(1-oxotetrahydrothiopyran-4-yl-phenyl]-2-oxooxazolidinone-5-carboxylic acid amide (PF-00422602), a new lead compound. J. Med. Chem. 50 (2007) 5886-5889.
23. V. Prachayasittikul, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, 8-Hydroxyquinolines: a review of their metal chelating properties and medicinal applications, Drug Des. Dev. Ther. 7 (2013) 1157-1178.
24. S. Sahni, S. Krishan, D. Palanimuthu, D.R. Richardson, The use of iron chelators in biocidal compositions: evaluation of patent, WO2014059417A1, Expert Opin. Ther. Pat. 25 (2015) 367-372.
25. S.J. Brickner, D.K. Hutchinson, M.R. Barbachyn, P.R. Manninen, D.A. Ulanowicz, S.A. Garmon, K.C. Grega, S.K. Hendges, D.S. Toops, C.W. Ford, G.E. Zurenko, 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. 39 (1996) 673-679.
26. Clinical and Laboratory Standards Institute, Performance Standards Antimicrobial Susceptibility Testing; Twenty-first Informational Supplement, M100-S21, Clinical and Laboratory Standards Institute, Wayne, PA, USA, 2011.
27. W.B. Im, S.H. Choi, J.-Y. Park. J. Finn, S.-H. Yoon, Discovery of torezolid as a novel 5-hydroxymethyl oxazolidinone antibacterial agent, Eur. J. Med. Chem. 46 (2011) 1027-1039.
28. V. Kalia, R. Miglani, K.P. Purnapatre, T. Mathur, S. Singhal, S. Khan, S.R. Voleti, D.J. Upadhyay, K.S. Saini, A. Rattan, V.S. Raj, Mode of action of ranbezolid against staphylococci and structural modeling studies of its interaction with ribosomes, Antimicrob. Agents Chemother. 53 (2009) 1427-1433.
29. A. Holt, D.F. Sharman, G.B. Baker, M.M. Palcic, A continuous spectrophotometric assay for monoamine oxidase and related enzymes in tissue homogenates, Anal. Biochem. 244 (1997) 384-392.
30. O.A. Phillips, L. Sharaf, R. D'Silva, E.E. Udo, L. Benov, Evaluation of the monoamine oxidases inhibitory activity of a small series of 5-(azole)methyl oxazolidinones, Eur. J. Pharm. Sci. 71 (2015) 56-61.
31. C.J. Fowler, K.F. Tipton, Deamination of 5-hydroxytryptamine by both forms of monoamine oxidase in the rat brain. J. Neurochem. 38 (3) (1982) 733-736.
32. H. Kinemuchi, M. Masato Jinbo, A. Tabata, Y. Toyoshima, Y. Arai, T. Tadano, K. Kisara, L. Oreland, 2-Bromoethylamine, a suicide inhibitor of tissue-bound semicarbazide-sensitive amine oxidase, Jpn. J. Pharmacol. 83 (2000) 164-166.