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
• Article Data: 16

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

General Description

(S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE is a chemical compound that is structurally complex. Its chemical properties are determined by multiple functional components. Features include a fluorine atom and an iodine atom incorporated within the phenyl group. It also incorporates chemical classes like acetamides and oxazolidinones. The latter are part of the larger class of compounds known as azolidines, which are saturated heterocycles of three or more nitrogen and sulfur atoms. (S)-N-[3-(3-FLUORO-4-IODO-PHENYL)-2-OXO-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE also possesses a chiral center at stereocenter, which is marked by the (S)- prefix.

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

• 519003-01-1 (5R)-5-(azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one 
• 507-09-5 tiolacetic acid 
• 487041-08-7 (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one 
• 501939-82-8 (5R)-methanesulfonic acid 3-(3-fluoro-4-iodophenyl)-2-oxo-oxazolidin-5-ylmethyl ester 
• 183905-31-9 N-[(2S)-2-acetoxy-3-chloropropyl]acetamide 
• 724793-80-0 (S)-2-((3-(3-fluoro-4-iodophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione 
• 72755-13-6 (3-fluoro-phenyl)-carbamic acid methyl ester 
• 1097722-53-6 (3-fluoro-4-iodophenyl)carbamic acid benzyl ester 
• 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 

Downstream Products

• 398152-56-2 N-{[(5S)-3-(4-ethynyl-3-fluorophenyl)-2-oxo-1,3-oxazolidin-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.

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.

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.