99827-73-3

Basic information

• Product Name: (R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE
• Synonyms: (R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE
• CAS NO: 99827-73-3
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• Mol File: 99827-73-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE(99827-73-3)
• EPA Substance Registry System: (R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE(99827-73-3)

Safety Data

• Hazardous Substances Data: 99827-73-3(Hazardous Substances Data)

Usage

Description

(R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE is a chemical compound belonging to the class of oxazolidin-2-one. It is an optically active compound with a specific configuration, featuring a reactive hydroxymethyl group and a phenyl ring. The oxazolidin-2-one structure provides stability and makes it a valuable compound in chemical research and development, with potential applications in various fields, including pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
(R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE is used as a building block for the synthesis of pharmaceutical compounds due to its unique structure and reactivity. (R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE's hydroxymethyl group and phenyl ring can be utilized in the development of new molecules with specific properties, contributing to the creation of novel drugs with targeted therapeutic effects.
Used in Agrochemical Industry:
(R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE is used as a building block for the synthesis of agrochemical compounds, such as pesticides and herbicides. Its unique structure and reactivity allow for the development of new molecules with specific properties, potentially leading to the creation of more effective and environmentally friendly agrochemicals.
Used in Chemical Research and Development:
(R)-5-(HYDROXYMETHYL)-3-PHENYLOXAZOLIDIN-2-ONE is used as a valuable compound in chemical research and development. Its unique structure and reactivity make it an important tool for exploring new chemical reactions and synthesizing novel molecules with specific properties, furthering the understanding of chemical processes and contributing to the advancement of various scientific fields.

Upstream product

• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 65031-96-1 (S)-glycidyl butyrate 
• 62-53-3 aniline 
• 29218-21-1 5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine 
• 124-38-9 carbon dioxide 
• 87508-50-7 (R)-3-(phenylamino)-1,2-propanediol 
• 918543-49-4 (S)-2-oxo-3-phenyloxazolidine-5-carboxylic acid 

Downstream Products

• 918543-49-4 (S)-2-oxo-3-phenyloxazolidine-5-carboxylic acid 
• 1066875-99-7 2-oxo-3-phenyl-oxazolidine-5-carbonyl chloride 
• 919081-33-7 2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 

Relevant articles and documents

COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

HUMAN IMMUNODEFICIENCY VIRUS PROTEASE INHIBITORS

The described invention relates to novel human immunodeficiency virus protease inhibitors, pharmaceutical compositions containing at least one such inhibitor, methods of preparing such inhibitors, and methods of utilizing such inhibitors to treat HIV and

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.