504438-22-6

Basic information

• Product Name: (R)-3-(3-fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one
• Synonyms: (R)-3-(3-fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one;Tedizolid intermediate I;(5R)-3-[3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(hydroxymethyl)-2-oxazolidinone;TD-2.1;(R)-(2-FLUORO-4-(5-(HYDROXYMETHYL)-2-OXOOXAZOLIDIN-3-YL)PHENYL)BORONIC ACID PINACOL ESTER;(5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
• CAS NO: 504438-22-6
• Molecular Formula: C₁₆H₂₁BFNO₅
• Molecular Weight: 337.1510432
• Product Categories: Tedizolid intermediates
• Mol File: 504438-22-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 469.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• PKA: 14.05±0.10(Predicted)
• CAS DataBase Reference: (R)-3-(3-fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(3-fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one(504438-22-6)
• EPA Substance Registry System: (R)-3-(3-fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one(504438-22-6)

Safety Data

• Hazardous Substances Data: 504438-22-6(Hazardous Substances Data)

Usage

General Description

"(R)-3-(3-fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(hydroxyMethyl)oxazolidin-2-one" is a complex chemical compound derived from various functional groups. The structure of this compound reveals its belonging to the class of organic compounds known as oxazolidinones, which contain an oxazolidinone group, a five-membered cyclic compound made up of three carbon atoms, one oxygen atom, and one nitrogen atom. The compound also contains the hyroxymethyl group (-CH2OH). Another primary feature of this compound is the presence of a boronic ester group, which has the 1,3,2-dioxaborolane skeleton, being a boron atom surrounded by two oxygen atoms forming a ring. Further, it has a fluorinated phenyl group attached, which has a fluorine atom bonded to a carbon atom of an aromatic ring. Due to its complex structure, the compound is likely to possess unique chemical behaviors and properties. The exact applications of this compound aren't specified but it could potentially be used in organic synthesis due to the presence of the boronic ester group.

Upstream product

• 510729-01-8 (4-bromo-3-fluorophenyl)carbamic acid benzyl ester 
• 73183-34-3 bis(pinacol)diborane 
• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 
• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 372-19-0 meta-fluoroaniline 
• 487041-08-7 (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one 

Downstream Products

• 1428738-42-4 (R)-3-(3-fluoro-4-(2-(2-methyl-2H-tetrazol-5-yl) isoindolin-5-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 1428960-57-9 (R)-3-(3-fluoro-4-(6-((2-methyl-2H-tetrazol-5-yl) amino)pyridin-3-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 1428738-46-8 (R)-3-(3-fluoro-4-(5-(2-methyl-2H-tetrazol-5-yl)-5,6-dihydro-4H-pyrrolo[3,4-d]thiazol-2-yl) phenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 700370-33-8 (5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one 
• 1188918-47-9 (R)‐3‐(3‐fluoro‐4‐(6‐((((S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐yl)oxy)methyl)pyridin‐3‐yl)phenyl)‐5‐(hydroxymethyl)oxazolidin‐2‐one 
• 1188405-34-6 (R)‐3‐(3‐fluoro‐4‐(6‐(((S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐yl)oxy)pyridin‐3‐yl)phenyl)‐5‐(hydroxymethyl)oxazolidin‐2‐one 
• 1188917-90-9 (R)‐3‐(3‐fluoro‐4‐(2‐(((S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐yl)oxy)pyrimidin‐5‐yl)phenyl)‐5‐(hydroxymethyl)oxazolidin‐2‐one 

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 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.

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.