856676-99-8

Basic information

• Product Name: methanesulfonic acid (5R)-3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl ester
• Synonyms: methanesulfonic acid (5R)-3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl ester
• CAS NO: 856676-99-8
• Molecular Weight: 368.18
• Mol File: 856676-99-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methanesulfonic acid (5R)-3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: methanesulfonic acid (5R)-3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl ester(856676-99-8)
• EPA Substance Registry System: methanesulfonic acid (5R)-3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl ester(856676-99-8)

Safety Data

• Hazardous Substances Data: 856676-99-8(Hazardous Substances Data)

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 510729-01-8 (4-bromo-3-fluorophenyl)carbamic acid benzyl ester 

Downstream Products

• 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 
• 1401341-71-6 C₂₆H₂₇FN₆O₈ 
• 1401341-72-7 C₃₆H₃₆FN₆O₈P 
• 1401341-74-9 C₂₂H₂₄FN₇O₄ 

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-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:

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.