87508-42-7

Upstream product

• 87508-50-7 (R)-3-(phenylamino)-1,2-propanediol 
• 105-58-8 Diethyl carbonate 
• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 60456-26-0 (R)-glycidyl butyrate 
• 62-53-3 aniline 
• 2603-10-3 N-phenyl methyl carbamate 
• 124-38-9 carbon dioxide 
• 29218-21-1 5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine 
• 239438-44-9 C₂₀H₂₀N₂O₆ 
• 239438-40-5 C₂₃H₂₄N₂O₆ 

Downstream Products

• 104392-60-1 (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate 
• 918543-48-3 (R)-2-oxo-3-phenyloxazolidine-5-carboxylic acid 
• 104392-66-7 (R)-2-<(3-phenyl-2-oxo-5-oxazolidinyl)methyl>phthalimide 
• 87508-45-0 (R)-4-[5-(hydroxymethyl)-2-oxo-3-oxazolidinyl]benzenesulfonamide 
• 121373-19-1 (R)-5-(fluoromethyl)-3-phenyl-2-oxooxazolidine 
• 96800-11-2 (S)-N-<<3-<4-(chlorosulfonyl)phenyl>2-oxo-5-oxazolidinyl>methyl> acetamide 
• 96800-34-9 (R)-(3-phenyl-2-oxo-5-oxazolidinyl)methyl azide 
• 96800-17-8 (S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide 
• 919081-52-0 2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 1066876-06-9 2-oxo-3-phenyl-oxazolidine-5-carbonyl chloride 
• 150880-20-9 Methanesulfonic acid (R)-2-oxo-3-phenyl-oxazolidin-5-ylmethyl ester 

Relevant academic research and scientific papers

Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral N-Aryl Epoxy Amines and CO2

A divergent coupling reaction was achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A gram-scale production of Linezolid was successfully achieved.

Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N-aryl-oxazolidinone-5-carboxamides as novel P2 ligands

Here, we describe the design, synthesis, and biological evaluation of novel HIV-1 protease inhibitors incorporating N-phenyloxazolidinone-5-carboxamides into the (hydroxyethylamino)sulfonamide scaffold as P2 ligands. Series of inhibitors with variations at the P2 phenyloxazolidinone and the P2′ phenylsulfonamide moieties were synthesized. Compounds with the (S)-enantiomer of substituted phenyloxazolidinones at P2 show highly potent inhibitory activities against HIV-1 protease. The inhibitors possessing 3-acetyl, 4-acetyl, and 3-trifluoromethyl groups at the phenyl ring of the oxazolidinone fragment are the most potent in each series, with Ki values in the low picomolar (pM) range. The electron-donating groups 4-methoxy and 1,3-dioxolane are preferred at P2′ phenyl ring, as compounds with other substitutions show lower binding affinities. Attempts to replace the isobutyl group at P1′ with small cyclic moieties caused significant loss of affinities in the resulting compounds. Crystal structure analysis of the two most potent inhibitors in complex with the HIV-1 protease provided valuable information on the interactions between the inhibitor and the protease enzyme. In both inhibitor-enzyme complexes, the carbonyl group of the oxazolidinone ring makes hydrogen-bond interactions with relatively conserved Asp29 residue of the protease. Potent inhibitors from each series incorporating various phenyloxazolidinone based P2 ligands were selected and their activities against a panel of multidrug-resistant (MDR) protease variants were determined. Interestingly, the most potent protease inhibitor starts out with extremely tight affinity for the wild-type enzyme (Ki = 0.8 pM), and even against the MDR variants it retains picomolar to low nanomolar Ki, which is highly comparable with the best FDA-approved protease inhibitors.

A short synthesis of oxazolidinone derivatives linezolid and eperezolid: A new class of antibacterials

Oxazolidinone derivatives such as Linezolid and Eperazolid, which are a new class of antibacterials, have been synthesized from 1,2,5,6-dianhydro- 3,4-isopropylidine-D-mannitol in good yield.

Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The 'B' group

The synthesis and structure/activity studies of the effect of varying the 'B' group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other 'B' functionalities by using S(N)2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different 'B' groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 μg/mL for the most active compounds described.