Literature DB >> 20031407

Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry.

Shanshan Yan1, Marvin J Miller, Timothy A Wencewicz, Ute Möllmann.   

Abstract

A series of novel oxazolidinone antibiotics having [2.2.1] and [2.2.2] bicyclic oxazine moieties at the C-5 side chain of the A-ring was synthesized by nitroso Diels-Alder reactions, from three linezolid analogs containing morpholine, piperazine and thiomorpholine, respectively, as the C-ring components. Subsequent N-O bond cleavage generated oxazolidinones with 4-amino cyclo-2-en-1-ol substituents. The in vitro antibacterial activities of these oxazolidinone analogs were evaluated. Copyright (c) 2009 Elsevier Ltd. All rights reserved.

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Year:  2009        PMID: 20031407      PMCID: PMC2818252          DOI: 10.1016/j.bmcl.2009.10.018

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  21 in total

1.  AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro.

Authors:  A Wookey; P J Turner; J M Greenhalgh; M Eastwood; J Clarke; C Sefton
Journal:  Clin Microbiol Infect       Date:  2004-03       Impact factor: 8.067

Review 2.  Oxazolidinone antibacterial agents: a critical review.

Authors:  Douglas K Hutchinson
Journal:  Curr Top Med Chem       Date:  2003       Impact factor: 3.295

3.  Linezolid resistance in a clinical isolate of Staphylococcus aureus.

Authors:  S Tsiodras; H S Gold; G Sakoulas; G M Eliopoulos; C Wennersten; L Venkataraman; R C Moellering; M J Ferraro
Journal:  Lancet       Date:  2001-07-21       Impact factor: 79.321

4.  Resistance mutations in 23 S rRNA identify the site of action of the protein synthesis inhibitor linezolid in the ribosomal peptidyl transferase center.

Authors:  P Kloss; L Xiong; D L Shinabarger; A S Mankin
Journal:  J Mol Biol       Date:  1999-11-19       Impact factor: 5.469

5.  Oxazolidinone resistance mutations in 23S rRNA of Escherichia coli reveal the central region of domain V as the primary site of drug action.

Authors:  L Xiong; P Kloss; S Douthwaite; N M Andersen; S Swaney; D L Shinabarger; A S Mankin
Journal:  J Bacteriol       Date:  2000-10       Impact factor: 3.490

6.  Comparative in vitro activity of PH-027 versus linezolid and other anti-anaerobic antimicrobials against clinical isolates of Clostridium difficile and other anaerobic bacteria.

Authors:  O A Phillips; V O Rotimi; W Y Jamal; M Shahin; T L Verghese
Journal:  J Chemother       Date:  2003-04       Impact factor: 1.714

7.  Linezolid resistance since 2001: SENTRY Antimicrobial Surveillance Program.

Authors:  Alan H Mutnick; Victoria Enne; Ronald N Jones
Journal:  Ann Pharmacother       Date:  2003-06       Impact factor: 3.154

Review 8.  Oxazolidinone structure-activity relationships leading to linezolid.

Authors:  Michael R Barbachyn; Charles W Ford
Journal:  Angew Chem Int Ed Engl       Date:  2003-05-09       Impact factor: 15.336

9.  Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections.

Authors:  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
Journal:  J Med Chem       Date:  1996-02-02       Impact factor: 7.446

Review 10.  Linezolid: the first oxazolidinone antimicrobial.

Authors:  Robert C Moellering
Journal:  Ann Intern Med       Date:  2003-01-21       Impact factor: 25.391

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  2 in total

1.  Synthesis of unique scaffolds via Diels-Alder cycloadditions of tetrasubstituted cyclohexadienes.

Authors:  Amanda L Jones; John K Snyder
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

2.  Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels-Alder reaction.

Authors:  Cheng Ji; Weimin Lin; Garrett C Moraski; Jane A Thanassi; Michael J Pucci; Scott G Franzblau; Ute Möllmann; Marvin J Miller
Journal:  Bioorg Med Chem       Date:  2012-04-18       Impact factor: 3.641

  2 in total

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