288570-67-2

Upstream product

• 372-19-0 meta-fluoroaniline 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 543-27-1 isobutyl chloroformate 
• 321430-28-8 3-fluorophenylcarbamic acid 2-methylpropyl ester 

Downstream Products

• 288570-70-7 2-methylpropyl [3-fluoro-4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamate 
• 288570-76-3 cis-2-methylpropyl [3-fluoro-4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]carbamate 
• 288570-80-9 trans-[3-fluoro-4-(1-oxo-tetrahydrothiopyran-4-yl)phenyl]carbamic acid isobutyl ester 
• 288570-82-1 2-methylpropyl [4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate 
• 288570-74-1 2-methylpropyl [4-(3,6-dihydro-1-oxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate 
• 288570-78-5 2-methylpropyl [3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate 
• 288570-72-9 [4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]carbamic acid 2-methylpropyl ester 
• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Antimicrobial quinolone derivatives and use of the same to treat bacterial infections

Substituted quinolone derivatives in which an oxazolidinone, isoxazolinone, or isoxazoline is covalently bonded to a quinolone, methods of using the quinolone derivatives, and pharmaceutical compositions containing the quinolone derivatives are disclosed. Methods of synthesizing these substituted quinolone derivatives are also disclosed, and in particular a method of manufacturing a 7-(2-oxo-1,3-oxazolidin-3-yl)aryl-3-quinolinecarboxylic acid by condensing a 4-(2-oxo-1,3-oxazolidin-5-yl)aryl boronic acid with a 7-halo-quinolone derivative. The quinolone derivatives possess antibacterial activity, and are effective against a number of human and veterinary pathogens in the treatment of bacterial diseases.

Novel oxazolidinone-quinolone hybrid antimicrobials

Antimicrobial compounds incorporating oxazolidinone and quinolone pharmacophore substructures have been synthesized and evaluated. Representative analogues 2, 5, and 6 display an improved potency versus linezolid against gram-positive and fastidious gram-negative pathogens. The compounds are also active against linezolid- and ciprofloxacin-resistant Staphylococcus aureus and Enterococcus faecium strains. The MOA for these new antimicrobials is consistent with a combination of protein synthesis and gyrase A/topoisomerase IV inhibition, with a structure-dependent degree of the contribution from each inhibitory mechanism.

2-Fluoro-(oxid-thiopyran-4-yl)benzene derivatives

Compounds that can be used in the synthesis of cyclic sulfur-containing oxazolidinone antibacterial agents include2-Methylpropyl [4-(3,6-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate,4(R)-trans-[3-[3-Fluoro-4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl 3-nitrobenzenesulfonate,1α,4β(S)-N-[[3-[3-Fluoro-4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanarnide monohydrate,4(R)-3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-(hydroxymethyl)-2-oxazolidinone,4(R)-[3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl 3-nitrobenzenesulfonate.

Process to prepare cyclic-sulfur fluorine containing oxazolidinones

The invention is a process for the preparation of cyclic-sulfur fluorine containing oxazolidinone antibacterial agents which utilizes the important tetrahydrothiopyran-o-fluorinated carbamate of formula (IV)

Stereodivergent synthesis of sulfoxide-containing oxazolidinone antibiotics

Carbamate 5 was prepared under mild conditions via a novel metal-halogen exchange procedure without competing benzyne formation. Selection of an appropriate oxidation/reduction sequence afforded access to either the cis- or trans-1-oxo-4-aryltetrahydrothi