268209-15-0

Basic information

• Product Name: (S)-tert-butyl 4-(4-(5-(aMinoMethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate
• Synonyms: (S)-tert-butyl 4-(4-(5-(aMinoMethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate
• CAS NO: 268209-15-0
• Molecular Formula: C₁₉H₂₇FN₄O₄
• Molecular Weight: 394.4404832
• Mol File: 268209-15-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-tert-butyl 4-(4-(5-(aMinoMethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 4-(4-(5-(aMinoMethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate(268209-15-0)
• EPA Substance Registry System: (S)-tert-butyl 4-(4-(5-(aMinoMethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate(268209-15-0)

Safety Data

• Hazardous Substances Data: 268209-15-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-tert-butyl 4-(4-(5-(aMinoMethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate is used as a potential drug or drug intermediate for its pharmacological activity due to the presence of an aminomethyl group and an oxazolidin-3-yl ring.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (S)-tert-butyl 4-(4-(5-(aMinoMethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate is used as a subject of study and development because of its diverse molecular functionalities and (S)-configuration at the tert-butyl carbon, which may lead to novel therapeutic applications.

Upstream product

• 154590-33-7 1-(2-fluoro-4-nitrophenyl)piperazine 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 874820-28-7 (5R)-[3-[3-fluoro-4-[N-t-butoxycarbonylpiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinylmethyl] nosylate 
• 369-34-6 3,4-difluoronitrobenzene 
• 154590-63-3 [N-3-(1-tert-butoxycarbonyl)-4-(2-fluoro-4-piperazinyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate 
• 154590-36-0 tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate 
• 154590-34-8 4-(2-fluoro-4-nitrophenyl)-piperazine-1-carboxylic acid tert butyl ester 
• 154590-35-9 tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate 
• 154590-64-4 (S)-N-[3-[3-fluoro-4-[N-t-butoxycarbonylpiperazin-1-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]azide 
• 154590-62-2 (R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate 

Downstream Products

• 348626-16-4 tert-butyl 4-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}piperazine-1-carboxylate 
• 392659-24-4 N-(3-{3-fluoro-4-[4-(5-formyl-furan-2-ylmethyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide 
• 548762-76-1 N-(3-{3-fluoro-4-[4-(5-hydroxymethyl-furan-2-ylmethyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide 
• 548762-73-8 N-[3-(3-fluoro-4-{4-[5-(hydroxyimino-methyl)-furan-2-ylmethyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide 
• 154590-66-6 (S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 268209-50-3 (R)-t-butyl 4-(2-fluoro-4-(5-(isothiocyanatomethyl)-2-oxo-oxazolidin-3-yl)phenyl)piperazine-1-carboxylate 
• 1140172-15-1 C₂₁H₂₇F₃N₄O₅ 

Relevant articles and documents

RETRACTED ARTICLE: Design, synthesis of novel oxazolidino-amides/sulfonamides conjugates and their impact on antibacterial activity

Abstract: In view of generating new compounds for future drug development, we have synthesized oxazolidinones library of aryl amides and aryl sulfonamide derivatives. These compounds were screened in vitro against panel of susceptible and resistant Gram-p

Synthesis, biological evaluation of new oxazolidino-sulfonamides as potential antimicrobial agents

A number of linezolid-like oxazolidino-sulfonamides (7a-y and 8a-b) were designed and synthesized with a view to develop antimicrobial agents with improved properties. Most of the synthesized compounds showed good to moderate activity against a panel of standard Gram-positive and Gram-negative bacteria and fungal strains. The compounds 7i and 7v exhibited significant activity, with a MIC value of 2.0-6.0 μg/mL against a panel of Gram-positive and Gram-negative bacteria. These compounds also showed activity against Candida albicans, with a MIC value of 4.0 μg/mL. A correlation of the antimicrobial activity with calculated lipophilicity values (C log P) is also presented.

Synthesis and antibacterial activities of N-substituted-glycinyl 1H-1,2,3-triazolyl oxazolidinones

A series of 1H-1,2,3-triazolyl piperazino oxazolidinone analogs with optionally varied glycinyl substitutions were synthesized and their antibacterial activity assessed against a panel of susceptible and resistant Gram-positive and selected Gram-negative

Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole) methyl oxazolidinones

A series of 5-(4-methyl-1,2,3-triazole)methyl oxazolidinones were synthesized and tested for their antibacterial activity against a panel of Gram-positive and Gram-negative clinical isolates in comparison with linezolid and vancomycin. Most of the compounds demonstrated strong to moderate in vitro antibacterial activity against susceptible and resistant Gram-positive pathogenic bacteria. Antibacterial activity varied with substitutions at the phenyl C4 position with bulky alkylcarbonyl and alkoxycarbonyl substitutions on the piperazine N4 being detrimental to antibacterial activity. Whereas the presence of the 4-methyl-1,2,3-triazole moiety in the acyl-piperazine containing analogs resulted in increased protein binding, and decreased antibacterial activity particularly against Streptococcus pneumoniae strains.

Novel and potent oxazolidinone antibacterials featuring 3-indolylglyoxamide substituents

Novel oxazolidinone antibacterials bearing a variety of 3-indolylglyoxamide substituents have been explored in an effort to improve the spectrum and potency of this class of agents. A subclass of this series was also made with the diversity at C-5 terminus. These derivatives have been screened against a panel of clinically relevant Gram-positive pathogens and fastidious Gram-negative organisms. Several analogs in this series were identified with in vitro activity superior to linezolid (MIC = 0.25-2 μg/mL). Compounds 10a, 10c, 10e and 10f displayed activity against linezolid resistant Gram-positive organisms (MIC = 2-4 μg/mL). Selected oxazolidinones were evaluated for in vivo efficacy against a mouse systemic infection model.

OXAZOLIDINONE DERIVATIVES AND USE THEREOF AS ANTIBIOTICS

The invention provides new oxazolidinone compounds of formula (I) wherein A is certain heterocycles optionally substituted; R1, R2, R3 and R4 are independently selected from -H and halogen; X is selected from O,

OXAZOLIDINONE COMPOUNDS AND COMPOSITIONS AND METHODS RELATED THERETO

The invention provides new oxazolidinones of formula (I), where R1, R2, R3 and R4 are independently selected from hydrogen, F and Cl; A is selected from certain heterocycles optionally substituted; X is selected from O, S, NRs and CR8Rg; Y is selected fro

Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid

Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles.

Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3-[4- (3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide (BAY 59-7939): An oral, direct factor Xa inhibitor

Despite recent progress in antithrombotic therapy, there is still an unmet medical need for safe and orally available anticoagulants. The coagulation enzyme Factor Xa (FXa) is a particularly promising target, and recent efforts in this field have focused on the identification of small-molecule inhibitors with good oral bioavailability. We identified oxazolidinone derivatives as a new class of potent FXa inhibitors. Lead optimization led to the discovery of BAY 59-7939 (5), a highly potent and selective, direct FXa inhibitor with excellent in vivo antithrombotic activity. The X-ray crystal structure of 5 in complex with human FXa clarified the binding mode and the stringent requirements for high affinity. The interaction of the neutral ligand chlorothiophene in the S1 subsite allows for the combination of good oral bioavailability and high potency for nonbasic 5. Compound 5 is currently under clinical development for the prevention and treatment of thromboembolic diseases.

antibacterial agents

The present invention provides novel compounds of the general formula (I) and their pharmaceutically acceptable salts. The present invention more particularly provides novel oxazolidinone derivatives of the general formula (I).