1123888-62-9

Basic information

• Product Name: (R)-(3-(4-(4-acetylpiperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate
• Synonyms: (R)-(3-(4-(4-acetylpiperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate
• CAS NO: 1123888-62-9
• Molecular Weight: 415.443
• Mol File: 1123888-62-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-(3-(4-(4-acetylpiperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(3-(4-(4-acetylpiperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate(1123888-62-9)
• EPA Substance Registry System: (R)-(3-(4-(4-acetylpiperazin-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate(1123888-62-9)

Safety Data

• Hazardous Substances Data: 1123888-62-9(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 154590-63-3 [N-3-(1-tert-butoxycarbonyl)-4-(2-fluoro-4-piperazinyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate 
• 154590-62-2 (R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate 
• 154590-36-0 tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate 
• 154590-35-9 tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate 
• 154590-34-8 4-(2-fluoro-4-nitrophenyl)-piperazine-1-carboxylic acid tert butyl ester 
• 154590-33-7 1-(2-fluoro-4-nitrophenyl)piperazine 
• 369-34-6 3,4-difluoronitrobenzene 

Downstream Products

• 1123888-68-5 (R)-S-[[3-[3-fluoro-4-(4-acetyl-1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetate 

Relevant articles and documents

Synthesis and biological evaluation of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives

Research activities on the oxazolidinone antibacterial class of compounds continue to focus on developing newer derivatives with improved potency, broad-spectrum activity and safety profiles superior to linezolid. Among the safety concerns with the oxazolidinone antibacterial agents is inhibition of monoamine oxidases (MAO) resulting from their structural similarity with toloxatone, a known MAO inhibitor. Diverse substitution patterns at the C-5 position of the oxazolidinone ring have been shown to significantly affect both antibacterial activity and MAO inhibition to varying degrees. Also, the antibacterial activity of compounds containing iron-chelating functionalities, such as the hydroxamic acids, 8-hydroxyquinolines and catechols have been correlated to their ability to alter iron intake and/or metabolism. Hence a series of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives were synthesized and evaluated for their antibacterial and MAO-A and -B inhibitory activities. The compounds were devoid of significant antibacterial activity but most demonstrated moderate MAO-A and -B inhibitory activities. Computer modeling studies revealed that the lack of potent antibacterial activity was due to significant steric interaction between the hydroxamic acid N-OH oxygen atom and one of the G2540 5′-phosphate oxygen atoms at the bacterial ribosomal binding site. Therefore, the replacement of the 5-acetamidomethyl group of linezolid with the 5-(N-hydroxyacetamido)methyl group present in the hydroxamic acid oxazolidinone derivatives was concluded to be detrimental to antibacterial activity. Furthermore, the 5-(hydroxamic acid)methyl oxazolidinone derivatives were also less active as MAO-A and -B inhibitors compared with linezolid and the selective inhibitors clorgyline and pargyline. In general, the 5-(hydroxamic acid)methyl oxazolidinone derivatives demonstrated moderate but selective MAO-B inhibitory activity.