556801-15-1Relevant academic research and scientific papers
Photochemistry of oxazolidinone antibacterial drugs
Fasani, Elisa,Tilocca, Fedele,Albini, Angelo
experimental part, p. 879 - 885 (2010/02/28)
The photochemistry of six N3-(3-fluoro-4-dialkylaminophenyl)-oxazolidinones known for their antimicrobial activity has been examined. All of these compounds are defluorinated in water (φdec ≈ 0.25) and in methanol (φdec ≈ 0.03), reas
An exploratory and mechanistic study of the defluorination of an (aminofluorophenyl)oxazolidinone: SN1(Ar*) vs. S R+N1(Ar*) mechanism
Fasani, Elisa,Tilocca, Fedele,Protti, Stefano,Merli, Daniele,Albini, Angelo
experimental part, p. 4634 - 4642 (2009/03/12)
The morpholinofluorophenyloxazolidinone 1 (the antibacterial drug linezolid) is found to undergo reductive defluorination upon irradiation in water (Φ 0.33), in some of the products accompanied by the simultaneous oxidative degradation of the morpholine side chain. In the presence of chloride, iodide and pyrrole, the fluorine is substituted by these groups (with pyrrole, in position 2). The defluorination is less efficient in methanol and mainly leads to reduction (Φ 0.053). These data can be accommodated through two different mechanisms, viz. either C-F bond heterolysis to give a phenyl cation [SN1(Ar*)], or ionization to give a radical cation [S R+N1(Ar*)]. Steady-state and time resolved data have been gathered for clarifying this issue. It is found that, indeed, ionization of 1 is efficient and proceeds from the singlet, but leads to no irreversible change. On the contrary, triplet 31 (lifetime 0.5 μs in MeOH, 0.1 μs in water) fragments and gives the corresponding triplet phenyl cation. The last intermediate explains well the observed hydrogen abstraction both inter- (from the solvent, when this is reducing) and intramolecularly (from the morpholine group), as well as addition to a charged anion or to a neutral π nucleophile such as pyrrole. The rationalization is supported by the study of some related molecules. Thus, the only photochemical reaction from the non fluorinated analogue of linezolid (that ionizes just as 1) is an inefficient degradation of the morpholine chain (Φ 0.001), while a simple model such as N-(2-fluorophenyl)morpholine undergoes photosolvolysis in water and is not trapped by pyrrole.
ISOLATED DESFLUORO-LINEZOLID, PREPARATION THEREOF AND ITS USE AS A REFERENCE MARKER AND STANDARD
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Page/Page column 13, (2010/11/27)
The present invention provides an isolated linezolid impurity, desfluoro linezolid, the preparation thereof and its use as a reference standard.
Practical Cu-catalyzed amination of functionalized heteroaryl halides
Yeh, Vince S.C.,Wiedeman, Paul E.
, p. 6011 - 6016 (2007/10/03)
The amination of a variety of highly functionalized heterocyclic bromides has been accomplished using a CuI/proline catalyst system. The current study significantly expanded the scope of the reaction by using examples relevant to drug discovery programs a
