444335-16-4

Basic information

• Product Name: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE
• Synonyms: 2-Oxazolidinone,3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-, (5R)-;Torezolid Intermediate3;(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE;(5R)-3-(4-broMo-3-fluorophenyl)-5-(hydroxyMethyl)-1,3-oxazolidin-2-one;(R)-3-(4-BroMo-3-fluorophenyl)-5-(hydroxyMethyl)oxazolidin-2-one;(5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-onea
• CAS NO: 444335-16-4
• Molecular Formula: C₁₀H₉BrFNO₃
• Molecular Weight: 290.09
• EINECS: 1592732-453-0
• Product Categories: Tedizolid intermediates
• Mol File: 444335-16-4.mol

Chemical Properties

• Boiling Point: 401.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.701±0.06 g/cm3(Predicted)
• Refractive Index: 1.589
• Storage Temp.: 2-8°C
• PKA: 14.05±0.10(Predicted)
• CAS DataBase Reference: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE(444335-16-4)
• EPA Substance Registry System: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE(444335-16-4)

Safety Data

• Hazardous Substances Data: 444335-16-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE is used as a potential precursor in the development of new antibiotics due to its structural features and the inherent properties of the oxazolidinone class of antibiotics. The presence of the bromine and fluorine atoms, along with the hydroxymethyl group, may contribute to its potential as a novel antimicrobial agent, offering a new avenue for combating resistant bacterial strains.
Additionally, given the compound's unique stereochemistry and functional groups, it may also be utilized in the development of other pharmaceutical agents, where its specific structural attributes could be leveraged for targeted therapeutic effects or improved pharmacokinetic profiles. Further research and development would be necessary to explore these potential applications fully.

InChI:InChI=1/C10H9BrFNO3/c11-8-2-1-6(3-9(8)12)13-4-7(5-14)16-10(13)15/h1-3,7,14H,4-5H2/t7-/m1/s1

Upstream product

• 372-19-0 meta-fluoroaniline 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 
• 510729-01-8 (4-bromo-3-fluorophenyl)carbamic acid benzyl ester 
• 60456-26-0 (R)-glycidyl butyrate 
• 656-65-5 3-fluoro-4-bromophenylamine 
• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 288570-67-2 2-methylpropyl (4-bromo-3-fluorophenyl)carbamate 

Downstream Products

• 444335-17-5 3-Nitro-benzenesulfonic acid (R)-3-(4-bromo-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester 
• 1188330-70-2 (R)-3-(4-bromo-3-fluoro-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-oxazolidin-2-one 
• 1401342-92-4 C₁₉H₂₂BFN₂O₆ 
• 504437-66-5 (S)‐N‐((3‐(3‐fluoro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)‐2‐oxooxazolidin‐5‐yl)methyl)acetamide 
• 1401341-59-0 C₂₁H₂₁FN₆O₄ 
• 1401341-60-3 C₂₀H₂₁FN₆O₃*ClH 
• 1401341-61-4 C₂₁H₂₃FN₆O₃ 
• 1401341-63-6 C₂₄H₂₇FN₆O₅ 
• 1401341-64-7 C₂₂H₂₅FN₆O₄ 
• 1401341-65-8 C₂₃H₂₅FN₆O₃ 
• 1401341-66-9 C₂₃H₂₃FN₆O₃ 
• 1401341-67-0 C₂₆H₃₁FN₆O₅ 
• 1401341-69-2 C₂₂H₂₃FN₆O₅ 
• 1401341-70-5 C₂₄H₂₅FN₆O₆ 

Relevant articles and documents

Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity

Previously we reported the results from an effort to improve Gram-negative antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chemistry campaign focused entirely on C-ring modifications. In that series we set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-negative activity: i) low MW (7.4 1), and iii) zwitterionic character at pH 7.4. Indeed, we observed that only analogs residing within these limits were able to overcome these barriers. Herein we report the results from a parallel effort where we explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, analysis of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ≤4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts.

OXAZOLIDINONE COMPOUNDS AND METHODS OF USE THEREOF AS ANTIBACTERIAL AGENTS

The present invention relates to oxazolidinone compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, E, and R1 are as defined herein. The present invention also relates to compositions which comprise at least one oxazolidinone compound of the invention. The invention also provides methods for inhibiting growth of mycobacterial cells as well as a method of treating mycobacterial infections by Mycobacterium tuberculosiscomprising administering a therapeutically effective amount of an oxazolidinone of the invention and/or apharmaceutically acceptable salt thereof, or a composition comprising such compound and/or salt.

A oxazolidinone compounds of preparation method (by machine translation)

The invention provides a oxazolidinone compounds of the preparation method. Specifically provides the type 1 compound preparation method. The formula 1 compound preparation method comprises, formula 2 N - methyl - D - grape amine compound in the presence of a catalytic reduction, direct formula 1 compound. The present invention provides a preparation has simplified the reaction step, shorten the reaction route, can make the final yield of the product is higher, and, better purity. (by machine translation)

Oxazolidinone-quinolone hybrid antibiotics

The present invention relates to compounds of the Formula (I) that are useful antimicrobial agents and effective against a variety of multi-drug resistant bacteria:

OXAZOLIDINONE HYDROXAMIC ACID COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS

This invention pertains generally to treating bacterial infections using organic compounds of Formula I. In certain aspects, the invention pertains to treating infections caused by Gram-negative bacteria. (I) wherein X, Y, R1, R2, R3, R4 and R5 and defined herein.

NOVEL OXAZOLIDINONE DERIVATIVE AND MEDICAL COMPOSITION CONTAINING SAME

Disclosed is a novel oxazolidinone derivative represented by Formula 1 above, in particular, a novel oxazolidinone compound having a cyclic amidoxime or cyclic amidrazone group. In Formula 1, R and Q are the same as defined in the detailed description. In addition, disclosed is a pharmaceutical composition for an antibiotic which includes the novel oxazolidinone derivative of Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient. The novel oxazolidinone derivative, the prodrug thereof, the hydrate thereof, the solvate thereof, the isomer thereof, and the pharmaceutically acceptable salt thereof have broad antibacterial spectrum against resistant bacteria, low toxicity and strong antibacterial effects against Gram-positive and Gram-negative bacteria and thus may be effectively used as antibiotics.

NOVEL OXAZOLIDINONE DERIVATIVE AND MEDICAL COMPOSITION CONTAINING SAME

Disclosed is a novel oxazolidinone derivative represented by Formula 1 above, in particular, a novel oxazolidinone compound having a cyclic amidoxime or cyclic amidrazone group. In Formula 1, R and Q are the same as defined in the detailed description. In addition, disclosed is a pharmaceutical composition for an antibiotic which includes the novel oxazolidinone derivative of Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient. The novel oxazolidinone derivative, the prodrug thereof, the hydrate thereof, the solvate thereof, the isomer thereof, and the pharmaceutically acceptable salt thereof have broad antibacterial spectrum against resistant bacteria, low toxicity and strong antibacterial effects against Gram-positive and Gram-negative bacteria and thus may be effectively used as antibiotics.

OXAZOLIDINONE ANTIBIOTICS CONTAINING FUSED RING

The present invention relates to a fused ring-containing oxazolidinone compound shown by general formula (I), a pharmaceutically acceptable salt thereof and a stereoisomer thereof, wherein R1, R2, R3, R4, R5, R6, A, B and C are as defined in the description. The present invention further relates to a method for preparing the compound, a pharmaceutical composition and a pharmaceutical formulation comprising the compound, and a use of the compound for the manufacture of a medicament for the treatment and/or prevention of infectious diseases and a use for the treatment and/or prevention of infectious diseases.

FUSED RING-CONTAINING OXAZOLIDINONES ANTIBIOTICS

The present invention relates to a fused ring-containing oxazolidinone compound shown by general formula (I), a pharmaceutically acceptable salt thereof and a stereoisomer thereof, wherein R1, R2, R3, R4, R5, R6, A, B and C are as defined in the description. The present invention further relates to a method for preparing the compound, a pharmaceutical composition and a pharmaceutical formulation comprising the compound, and a use of the compound for the manufacture of a medicament for the treatment and/or prevention of infectious diseases and a use for the treatment and/or prevention of infectious diseases.

BICYCLIC NITROIMIDAZOLES COVALENTLY LINKED TO SUBSTITUTED PHENYL OXAZOLIDINONES

The current invention provides a series of bicyclic nitroimidazole- substituted phenyl oxazolidinones in which a bicyclic nitroimidazole pharmacophore is covalently bonded to a phenyl oxazolidinone, their pharmaceutical compositions, and the method of use of the compositions for prevention and treatment of bacterial infections. The bicyclic nitroimidazole-substituted phenyl oxazolidinones possess surprising antibacterial activity against wild- type and resistant strains of pathogens, and are therefore useful for the prevention, control and treatment of a number of human and veterinary bacterial infections caused by these pathogens, such as Mycobacterium tuberculosis.