790703-49-0

Basic information

• Product Name: 2-Oxazolidinone, 3-[3-fluoro-4-(phenylmethoxy)phenyl]-5-(hydroxymethyl)-, (5R)-
• CAS NO: 790703-49-0
• Molecular Formula: C17H16FNO4
• Molecular Weight: 317.317
• Mol File: 790703-49-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 3-[3-fluoro-4-(phenylmethoxy)phenyl]-5-(hydroxymethyl)-, (5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 3-[3-fluoro-4-(phenylmethoxy)phenyl]-5-(hydroxymethyl)-, (5R)-(790703-49-0)
• EPA Substance Registry System: 2-Oxazolidinone, 3-[3-fluoro-4-(phenylmethoxy)phenyl]-5-(hydroxymethyl)-, (5R)-(790703-49-0)

Safety Data

• Hazardous Substances Data: 790703-49-0(Hazardous Substances Data)

Upstream product

• 403-19-0 2-fluoro-4-nitrophenol 
• 100-39-0 benzyl bromide 
• 369-34-6 3,4-difluoronitrobenzene 
• 100-51-6 benzyl alcohol 
• 168268-00-6 4-(benzyloxy)-3-fluoroaniline 
• 76243-24-8 1-(benzyloxy)-2-fluoro-4-nitrobenzene 
• 790703-40-1 (4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester 
• 60456-26-0 (R)-glycidyl butyrate 

Downstream Products

• 926279-54-1 (5R)-3-(4-benzyloxy-3-fluoro-phenyl)-5-(isoxazol-3-yloxymethyl)-oxazolidin-2-one 
• 1025097-10-2 1-cyclopropyl-6-fluoro-7-[4-({2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl] phenoxy}methyl)-4-hydroxypiperidin-1-yl]-4-oxo-1,4-dihydroquinolin-3-carboxylic acid 
• 1025097-81-7 1-cyclopropyl-6-fluoro-7-{(RS)-3-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-3-hydroxy-pyrrolidin-1-yl}-4-oxo-1,4dihydro-quinoline-3-carboxylic acid 
• 1025097-90-8 (RS)-3-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 1025098-00-3 7-(4-(bis-benzyloxy-phosphoryloxy)-4-{4-[(R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid benzyl ester 
• 1025097-79-3 7-(4-{4-[(R)-5-((S)-2-amino-propionyloxymethyl)-2-oxo-oxazolidin-3yl]-2-fluoro-phenoxymethyl}-4-hydroxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4oxo-1,4-dihydro-quinoline-3-carboxylic acid hydrochloride 
• 1025097-67-9 7-(4-{4-[(R)-5-((S)-2-tert-butoxycarbonylamino-propionyloxymethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-hydroxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid benzyl ester 
• 1025097-71-5 7-(4-{4-[(R)-5-(bis-benzyloxy-phosphoryloxymethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-hydroxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 1025098-02-5 7-{4-[4-((R)-5-acetoxymethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenoxymethyl]-4-phosphonooxy-piperidin-1-yl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid benzyl ester 
• 1025097-69-1 7-(4-{4-[(R)-5-((S)-2-tert-butoxycarbonylamino-propionyloxymethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-hydroxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 1025097-98-6 7-(4-{4-[(R)-5-(tert-butyldimethyl-silanyloxymethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-hydroxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid benzyl ester 
• 1025097-18-0 1-cyclopropyl-6-fluoro-7-{4-[2-fluoro-4-((R)-2-oxo-5-phosphonooxymethyl-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 1025097-40-8 1-cyclopropyl-6-fluoro-7-{4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-phosphonooxy-piperidin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 1025097-65-7 1-cyclopropyl-6-fluoro-7-{4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxymethyl]-4-hydroxy-piperidin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis, antibacterial activities, mode of action and acute toxicity studies of new oxazolidinone-fluoroquinolone hybrids

To combat bacterial resistance, a series of new oxazolidinone-fluoroquinolone hybrids have been synthesized and characterized. All synthetic hybrids were preliminarily evaluated for their in vitro antibacterial activities against 6 standard strains and 3 clinical isolates. The majority of hybrids displayed excellent activities against Gram-positive bacteria, but limited activities against Gram-negative bacteria. Hybrids OBP-4 and OBP-5 were found to be the most promising compounds. Further, in vitro antibacterial activities, mode of action and acute toxicity in mice of hybrids OBP-4 and OBP-5 were investigated. Hybrids OBP-4 and OBP-5 exhibited potent activities against Gram-positive bacteria, including drug-resistant strains. Correspondingly, studies on the mode of action of hybrids OBP-4 and OBP-5 indicated a strong inhibitory activity on protein synthesis by binding the active site of 50S subunit, but a weak inhibitory action on DNA synthesis. In addition, LD50 values of hybrids OBP-4 and OBP-5 in the acute oral toxicity were larger than 2000 mg/kg, suggesting a good safety profile.

Cadazolid key intermediate preparation method

The invention discloses a cadazolid key intermediate preparation method, which comprises: reducing a compound represented by a formula (2) in a solvent in the presence of one or a combination of a metal element-containing compound and a reducing agent to obtain a reaction solution containing a compound represented by a formula (3), and collecting the compound 4-benzyloxy-3-fluoroaniline represented by the formula (3) from the reaction product. According to the present invention, the expensive platinum carbon is replaced with the composition of ferric chloride hexahydrate and hydrazine hydrate,the reducing reaction time is shortened to about 5 h from 48 h, the expensive reducing agent is not required, the reaction time is shortened, and the conversion rate of the raw materials is improved;and the whole route has characteristics of mild reaction, simple operation and low cost, and is suitable for industrial production. The formulas (2) and (3) are defined in the specification.

INTERMEDIATE PRODUCTS FOR PRODUCING OXAZOLIDINONE-QUINOLONE HYBRIDS

The invention relates to intermediate products (ZP) for a novel and efficient synthesis of compounds, wherein the pharmacophores of quinolone and oxazolidinone are linked together by means of a chemically stable linker.