149524-45-8

Basic information

• Product Name: (S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE
• Synonyms: (S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE;AcetaMide, N-[[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]Methyl]-
• CAS NO: 149524-45-8
• Molecular Formula: C₁₂H₁₂FIN₂O₃
• Molecular Weight: 378.14
• Mol File: 149524-45-8.mol

Chemical Properties

• Boiling Point: 520.6 °C at 760 mmHg
• Flash Point: 268.6 °C
• Appearance: /
• Density: 1.736 g/cm³
• Vapor Pressure: 6.14E-11mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: 2-8°C
• PKA: 15.53±0.46(Predicted)
• CAS DataBase Reference: (S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE(149524-45-8)
• EPA Substance Registry System: (S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE(149524-45-8)

Safety Data

• Hazardous Substances Data: 149524-45-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE is used as a potential therapeutic agent for various medical applications. Its unique structure and functional groups may contribute to its activity against specific biological targets, making it a candidate for drug development.
Used in Chemical Research:
In the field of chemical research, (S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE serves as a subject of study for understanding the properties and reactivity of complex molecules. Its synthesis and modification can provide insights into the development of new chemical compounds with potential applications in various industries.
Used in Material Science:
(S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE may be utilized in material science for the development of new materials with specific properties. Its structural features could be exploited to create materials with tailored characteristics for use in various applications, such as sensors, catalysts, or advanced materials for electronics and energy storage.

InChI:InChI=1/C12H12FIN2O3/c1-7(17)15-5-9-6-16(12(18)19-9)8-2-3-11(14)10(13)4-8/h2-4,9H,5-6H2,1H3,(H,15,17)/t9-/m0/s1

Upstream product

• 1097722-53-6 (3-fluoro-4-iodophenyl)carbamic acid benzyl ester 
• 183905-31-9 N-[(2S)-2-acetoxy-3-chloropropyl]acetamide 
• 72755-13-6 (3-fluoro-phenyl)-carbamic acid methyl ester 
• 724793-80-0 (S)-2-((3-(3-fluoro-4-iodophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione 
• 501939-82-8 (5R)-methanesulfonic acid 3-(3-fluoro-4-iodophenyl)-2-oxo-oxazolidin-5-ylmethyl ester 
• 487041-08-7 (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one 
• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 
• 139071-79-7 (S)-N-[[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 372-19-0 meta-fluoroaniline 
• 380380-56-3 (S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one 
• 149524-44-7 (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide 
• 380380-55-2 [(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate 

Downstream Products

• 843647-51-8 (S)-N-((3-(2-fluoro-4'-(hydroxymethyl)-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide 
• 504437-66-5 (S)‐N‐((3‐(3‐fluoro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)‐2‐oxooxazolidin‐5‐yl)methyl)acetamide 
• 1188918-12-8 (S,S)-N-(3-{3-fluoro-4-[3-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-prop-1-ynyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide 
• 916888-22-7 (5S)-N-{3-[2-fluoro-4'-({[1-(4-methoxybenzyl)-1H-[1,2,3]triazol-5-ylmethyl]amino}methyl)biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}acetamide hydrochloride 
• 916888-21-6 (5S)-N-{3-[2-fluoro-4'-({[1-(4-methoxybenzyl)-1H-[1,2,3]triazol-4-ylmethyl]amino}methyl)biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}acetamide hydrochloride 
• 916888-20-5 (5S)-{4'-[5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2'-fluorobiphenyl-4-ylmethyl}-[1-(4-methoxybenzyl)-1H-[1,2,3 ]triazol-5-ylmethyl]carbamic acid tert-butyl ester 
• 916888-19-2 (5S)-{4'-[5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2'-fluorobiphenyl-4-ylmethyl}-[1-(4-methoxybenzyl)-1H-[1,2,3 ]triazol-4-ylmethyl]carbamic acid tert-butyl ester 
• 1333992-01-0 C₂₃H₁₉FN₆O₃ 
• 1333992-03-2 C₂₄H₂₁FN₆O₄ 
• 1333992-05-4 C₂₁H₁₇FN₆O₃S 
• 869884-78-6 (5S)-N-[3-(2-fluoro-4'-{[(1H-[1,2,3]triazol-4-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]acetamide 
• 869884-77-5 (5S)-N-[3-(2-fluoro-4'-{[(1H-[1,2,3]triazol-4-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]acetamide hydrochloride 

Relevant articles and documents

Design and synthesis of biaryloxazolidinone derivatives containing a rhodanine or thiohydantoin moiety as novel antibacterial agents against Gram-positive bacteria

Novel biaryloxazolidinone derivatives containing a rhodanine or thiohydantoin moiety were designed, synthesized and evaluated for their antibacterial activity. The key compounds 7 and 9 were synthesized by the knoevenagel condensation of intermediate aldehyde 5 with rhodanine derivatives 6a?6b. The preliminary study showed that compounds 7, 9 and 10e exhibited potent antibacterial activity with MIC values of 0.125 μg/mL against S. aureus, MRSA, MSSA, LREF and VRE pathogens, using linezolid and radezolid as the positive controls. The most promising compound 10e exhibited potent antibacterial activity against tested clinical isolates of MRSA, MSSA, VRE and LREF with MIC values in the range of 0.125–0.5 μg/mL, and the potency of 10e against clinical isolates of LREF was 64-fold higher than that of linezolid. Moreover, compound 10e was non-cytotoxic with an IC50 value of 91.04 μM against HepG2 cell. Together, compound 10e might serve as a novel antibacterial agent for further investigation.

Installation of an aryl boronic acid function into the external section of N-aryl-oxazolidinones: Synthesis and antimicrobial evaluation

N-aryl-oxazolidinones is a prominent family of antimicrobials used for treating infections caused by clinically prevalent Gram-positive bacteria. Recently, boron-containing compounds have displayed intriguing potential in the antibiotic discovery setting. Herein, we report the unprecedented introduction of a boron-containing moiety such as an aryl boronic acid in the external region of the oxazolidinone structure via a chemoselective acyl coupling reaction. As a result, we accessed a series of analogues with a distal aryl boronic pharmacophore on the oxazolidinone scaffold. We identified that a peripheric linear conformation coupled with freedom of rotation and no further substitution on the external aryl boronic ring, an amido linkage with hydrogen bonding character, in addition to a para-relative disposition between boronic group and linker, are the optimal combination of structural features in this series for antimicrobial activity. In comparison to linezolid, the analogue comprising all those features, compound 20b, displayed levels of antimicrobial activity augmented by an eight-fold to a thirty-two-fold against a panel of Gram-positive strains, and a near one hundred-fold against Escherichia coli JW5503, a Gram-negative mutant strain with a defective efflux capability.

Incorporation of a chiral gem-disubstituted nitrogen heterocycle yields an oxazolidinone antibiotic with reduced mitochondrial toxicity

gem-Disubstituted N-heterocycles are rarely found in drugs, despite their potential to improve the drug-like properties of small molecule pharmaceuticals. Linezolid, a morpholine heterocycle-containing oxazolidinone antibiotic, exhibits significant side effects associated with human mitochondrial protein synthesis inhibition. We synthesized a gem-disubstituted linezolid analogue that when compared to linezolid, maintains comparable (albeit slightly diminished) activity against bacteria, comparable in vitro physicochemical properties, and a decrease in undesired mitochondrial protein synthesis (MPS) inhibition. This research contributes to the structure-activity-relationship data surrounding oxazolidinone MPS inhibition, and may inspire investigations into the utility of gem-disubstituted N-heterocycles in medicinal chemistry.

Oxazolidinone compound containing combined aromatic hydrazine and its preparation method

The invention relates to oxazolidinone compound containing combined aromatic hydrazine shown in general formula I, its optical isomer, pharmaceutical acceptable salt and/or solvent compound, and it preparation method, and the drug composition containing the compound, wherein the substituent groups R1, R2, R3, X and A rings have the meaning given in the specification. The invention further relatesto the compound, the substituent group, solvent compound or application of its prodrug using as antibacterial drug in treatment, and application of treating gram positive bacterial infection and mycobacterium tuberculosis infection especially.

Synthesis and antibacterial activity evaluation of novel biaryloxazolidinone analogues containing a hydrazone moiety as promising antibacterial agents

A series of linezolid analogues containing a hydrazone moiety were designed, synthesized and evaluated for their antibacterial activity. Most compounds exhibited more potent antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens as compared with linezolid and radezolid. Compounds 9a, 9c, 9f, 9g, 10m and 10t were more potent against tested clinical isolates of MRSA, MSSA, VRE and LREF as compared to linezolid. Compound 9a exhibited comparable activity with linezolid against human MAO-A for safety evaluation and showed moderate metabolism in human liver microsome. The most promising compound 9a showed remarkable antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens with MIC value of 0.0675 mg/mL, respectively, which was 15- to 30-fold more potent than linezolid.

Heterocycle-containing biaryl oxazolidinone compound and preparation method thereof

The invention relates to a heterocycle-containing biaryl oxazolidinone compound with the structural formula as shown in the figure I in the specification, or an optical isomer and a pharmaceutically acceptable salt and/or solvate thereof, a preparation method for the heterocycle-containing biaryl oxazolidinone compound as well as the optical isomer and the pharmaceutically acceptable salt and/or solvate thereof, and a pharmaceutical composition containing the compound. According to the heterocycle-containing biaryl oxazolidinone compound, the substituent groups R1, R2, R3, R4 and A-ring have the meanings given in the specification. The invention also relates to application of the compound as well as the pharmaceutically acceptable salt and solvate or a prodrug thereof as an antibacterial drug in treatment, especially in treatment of gram-positive bacterial infection and mycobacterium tuberculosis infection. (Please see the figure I in the specification for the structural formula of theheterocyclic ring-containing biaryl oxazolidinone compound.).

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.

Preparation method of biaryl oxazolidone intermediate

The invention relates to a preparation method of a biaryl oxazolidone intermediate (5S)-N-[[3-(3-fluoro-4-iodophenyl)-2-oxooxazolidine-5-ol]methyl]acetamine (I). According to the method, the intermediate is prepared with m-fluoroaniline as an initial raw material through amino protection, iodination and cyclization sequentially. Compared with a reported preparation method of the biaryl oxazolidone intermediate, the method adopts a short route, increases the yield, greatly reduces the cost and is more suitable for industrial production.

TOPICAL FORMULATIONS OF BIARYL HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF

The present invention relates to topical formulations of biaryl heterocyclic compounds and methods of use thereof for treating acne and other skin infections caused or mediated by Streptococcus pyogenes, Streptococcus agalactiae, Haemophilus influenza, Trichomonas vaginalis, Klebsiella sp., Enterobacter sp., Proteus sp., Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus (including Methicillin-resistant Staphylococcus aureus (MRSA)) in a patient in need thereof. In certain embodiments, the acne or other skin infection is caused or mediated by Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus.

METHOD FOR TREATING, PREVENTING, OR REDUCING THE RISK OF SKIN INFECTION

The present invention relates to methods for treating acne and other skin infections caused or mediated by Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus in a patient with a safe and effective amount of a topically applied oxazolidinone antibiotic compound.