Synthesis of novel oxazolidinone antimicrobial agents

Ebner, D. C.; Culhane, Jeffrey C.; Winkelman, Tyler N.A.; Haustein, Mitchell D.; Ditty, Jayna L.; Ippoliti, J. Thomas

doi:10.1016/j.bmc.2007.11.040

Cited by 30 publications

(26 citation statements)

References 15 publications

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“…[115] The MIC against S. aureus was determined to be 2-3 mg mL À1 for one of the compounds. This compound has similar antimicrobial activity against S. aureus as linezolid, (4 mg mL À1 ).…”

Section: Antifungal and Antibacterialsmentioning

confidence: 99%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,143

508

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The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of click chemistry due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.

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Section: Antifungal and Antibacterialsmentioning

confidence: 99%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,143

508

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“…In the past decade oxazolidonone compounds have attracted much attention because of their biologically properties [6][7][8][9]. They are totally synthetic antibacterial agents with a novel mechanism of action involving the inhibition of bacterial protein synthesis at a very early stage, thus disrupting chain initiation [9,10].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C₁₅H₁₇FN₂O₄

Samipillai

Govender

Kruger

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C15H17FN 2 O4, monoclinic, P21/c (no. 14), a = 12.4266(11) Å, b = 6.6865(5) Å, c = 17.1510(15) Å, CCDC no.: 1534697The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialA solution of 3-fluoro-4-(4-morpholinyl)-aniline (1.0 eq.) and carbonyldiimidazole (CDI) (1.2 eq.) in dichloromethane (DCM) (10 mL) was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure and the resulting residue was purified via column chromatography to afford pure product.

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“…The necessity of developing convenient procedures for the preparation of potential biologically active linezolid analogs in optically pure form led to the discovery of Manninen reaction, where commercially available (R)-glycidyl butyrate acts as epoxide. This reagent was used to obtain key intermediates 41 [20], 42 [85], and 43 [86,87] in the syntheses of antibacterial agents and other were also synthesized in this way [86] (Scheme 22). The procedure for the synthesis of oxazolidinone antibiotics 46 with the use of (±)-glycidylacetamide was covered by patent [88].…”

Section: Heterocyclization Of Epoxy Carbamatesmentioning

confidence: 99%