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STEREOCHEMISTRY OF RINGS. XV. gamma-LACTONE DERIVATIVES. Part 9. X-ray structure of 5-chloromethyl-2-oxazolidinone

C4H6NO2Cl (Mr=135.55) crystallizes in the monoclinic system, space group P21/c with a=9.257(2), b=5.181(3), c=12.620(2) Angstroem, beta=110.75(4) deg, V=566.0(4) Angstroem3, Z=4, Dc=1.59 g cm-1, mu(CuKalpha)=53.16 cm-1, lambda/=1.5418 Angstroem, F(000)=280.The oxazolidinone ring is approximately planar; the geometrical parameters reveal a certain degree of electronic delocalization in the molecule.The CH2Cl group assumes an axial position.The molecules are joined in dimers by strong N-H…O hydrogen bonds.

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Regioselective anodic alpha-methoxylation of 2-oxazolidinone on boron doped diamond in acidic methanol medium

For the first time, anodic methoxylation of 2-oxazolidinone was investigated on boron doped diamond (BDD) in CH3OHH 2SO4 medium. Voltammetric studies reveal that the 2-oxazolidinone gets oxidised at a potential of 1.5 V vs. SCE on the BDD, whereas on the graphite, the anodic oxidation takes place in the potential region of methanol oxidation. Galvanostatic electrolysis results in the formation of 4-methoxy-2-oxazolidinone (MOD) as a single product in high yield on the BDD and multiple products, along with MOD on the graphite. Generation of methoxy radical on the BDD was confirmed by Electron Spin Resonance (ESR) spectroscopy.

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N-thiolated 2-oxazolidinones: A new family of antibacterial agents for methicillin-resistant Staphylococcus aureus and Bacillus anthracis

In this report, we describe a new family of N-thiolated 2-oxazolidinones having antibacterial activity against methicillin-resistant Staphylococcus aureus and Bacillus anthracis. The effect of ring substituents and stereochemistry on antibacterial activity of these oxazolidinones closely parallels that previously reported for N-thiolated beta-lactam antibiotics.

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Methyl-thiazoles: A novel mode of inhibition with the potential to develop novel inhibitors targeting InhA in mycobacterium tuberculosis

InhA is a well validated Mycobacterium tuberculosis (Mtb) target as evidenced by the clinical success of isoniazid. Translating enzyme inhibition to bacterial cidality by targeting the fatty acid substrate site of InhA remains a daunting challenge. The recent disclosure of a methyl-thiazole series demonstrates that bacterial cidality can be achieved with potent enzyme inhibition and appropriate physicochemical properties. In this study, we report the molecular mode of action of a lead methyl-thiazole, along with analogues with improved CYP inhibition profile. We have identified a novel mechanism of InhA inhibition characterized by a hitherto unreported “Y158-out” inhibitor-bound conformation of the protein that accommodates a neutrally charged “warhead”. An additional novel hydrophilic interaction with protein residue M98 allows the incorporation of favorable physicochemical properties for cellular activity. Notably, the methyl-thiazole prefers the NADH-bound form of the enzyme with a Kd of ?13.7 nM, as against the NAD+-bound form of the enzyme.

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The therapeutic compound, use and related method (by machine translation)

PROBLEM TO BE SOLVED: To provide a pharmaceutical composition containing a compound or its salt which prevents or treats a central nervous system disease in which integration dysfunction syndrome and agnosia are enumerated as exemplary disorders.SOLUTION: The pharmaceutical composition includes the compound or its salt represented by chemical formula (A) which modulates striatal-enriched protein tyrosine phosphatase (STEP).

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N-Acylation of Oxazolidinones via Aerobic Oxidative NHC Catalysis

The first N-acylation of synthetically useful oxazolidinones with aldehydes using aerobic oxidative NHC catalysis is reported. The reaction offers a broad scope of functionalized oxazolidinones in good to excellent yields. Careful choice of electron transfer mediators proved pivotal to achieve efficient aerobic N-acylation, which has previously proven difficult using NHC catalysis. The methodology allows a mild entry to acylated oxazolidinones, avoiding the use of hazardous and reactive prefunctionalized substrates.

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RECYCLIZATION REACTIONS OF SMALL RINGS. 8. SYNTHESIS OF 5-SUBSTITUTED 2-OXAZOLIDONES FROM THIAZOLIDINE-2,4-DIONE AND OXIRANES

Treatment of oxiranes with thiazolidine-2,4-dione gives N-(2-hydroxypropyl)-thiazolidine-2,4-diones which can recyclize to 5-substituted 2-oxazolidones in basic medium.

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