80-65-9

Basic information

• Product Name: 3-AMINO-2-OXAZOLIDINONE
• Synonyms: 3-AMINO-2-OXAZOLIDINONE;AOZ;3-Amino-1,3-oxazolidin-2-one;NSC 111187;NSC 196570;NSC 38250;2-Oxazolidinone,3-amino-(6CI,7CI,8CI,9CI);3-AMINO-OXAZOLIDINONE
• CAS NO: 80-65-9
• Molecular Formula: C₃H₆N₂O₂
• Molecular Weight: 102.09
• EINECS: 201-299-2
• Product Categories: VARIOUSAMINE;Isoxazoles, Oxadiazoles, Oxazoles;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Heterocycles
• Mol File: 80-65-9.mol

Chemical Properties

• Melting Point: 65-67 °C
• Boiling Point: 167.2 °C at 760 mmHg
• Flash Point: 54.9 °C
• Appearance: /
• Density: 1.179
• Vapor Pressure: 1.72mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.24±0.20(Predicted)
• BRN: 109430
• CAS DataBase Reference: 3-AMINO-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-2-OXAZOLIDINONE(80-65-9)
• EPA Substance Registry System: 3-AMINO-2-OXAZOLIDINONE(80-65-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 80-65-9(Hazardous Substances Data)

Usage

Uses

Used in Environmental Monitoring:
3-AMINO-2-OXAZOLIDINONE is used as a marker for environmental contamination, as it can be detected in various environmental samples, indicating the presence of Furazolidone and Nitrofuran compounds.
Used in Food Safety:
3-AMINO-2-OXAZOLIDINONE is used as an indicator of food contamination, as its presence in food products may suggest the use of Furazolidone and Nitrofuran compounds during food production or processing.
Used in Heat Processing Industry:
3-AMINO-2-OXAZOLIDINONE is used as a marker for heat processing contaminants, as it can be formed during the heat treatment of certain materials, indicating potential health risks associated with the consumption of these products.

InChI:InChI=1/C3H6N2O2/c4-5-1-2-7-3(5)6/h1-2,4H2

Upstream product

• 67-45-8 furazolidone 
• 109-84-2 2-hydroxyethylhydrazine 
• 616-38-6 carbonic acid dimethyl ester 
• 497-25-6 dimethylenecyclourethane 
• 105-58-8 Diethyl carbonate 
• 98025-70-8 carbazic acid-(2-chloro-ethyl ester) 
• 85430-60-0 3-nitro-1,3-oxazolidine-2-one 

Downstream Products

• 67-45-8 furazolidone 
• 3318-78-3 3-[3-(5-nitro-[2]furyl)-allylidenamino]-oxazolidin-2-one 
• 4341-14-4 3-[(phenylmethylene)amino]-2-oxazolidinone 
• 36146-44-8 2-azepan-1-yl-3-[(2-oxo-oxazolidin-3-ylimino)-methyl]-pyrido[1,2-a]pyrimidin-4-one 
• 951779-31-0 C₁₂H₁₁ClF₃N₃O₄S 
• 1013312-35-0 3-[[4-carboxyphenyl]methylene]amino-2-oxazolidinone 
• 951779-50-3 C₁₃H₁₃ClF₃N₃O₄S 
• 860006-40-2 3-(2-bromo-benzylidene)amino-2-oxazolidinone 
• 860006-42-4 3-(2-methyl-benzylidene)amino-2-oxazolidinone 
• 860006-38-8 3-(4-methoxy-benzylidene)amino-2-oxazolidinone 
• 860006-36-6 3-(benzylidene)amino-2-oxazolidinone 

Relevant articles and documents

Preparation method and application of 3-amino-2-oxazolidinone derivative

The invention discloses a preparation method and application of a 3-amino-2-oxazolidinone derivative. The invention relates to a derivative of a general formula I with a bacterial quorum sensing regulation effect, wherein definitions of substituent groups in the general formula I are described in the specification; a preparation method of the compound of general formula I; a pharmaceutical composition comprising the compound of general formula I; and application of the compound of general formula I in the preparation of medicaments. Biological activity detection is carried out on the compound shown as the general formula I, the regulation effect of the compound shown as the general formula I on bacterial quorum sensing is further proved, an experimental basis is provided for a new strategy for treating diseases caused by drug-resistant gram-negative bacteria, and an important research value is achieved for solving the drug resistance problem.

Synthetic method of furazolidone metabolite AOZ

The invention discloses a preparation method of 3-amino-2-oxazolidinone (AOZ). The method comprises the following steps: 1) carrying out a reaction on ethylene glycol and PBr3 to obtain 2-bromoethanol; 2) in the presence of an alkali, carrying out a reaction on NH2NH2Boc and 2-bromoethanol to obtain Boc protected 2-hydrazinoethanol; 3) in the presence of an alkali, carrying out a reaction on Boc protected 2-hydrazinoethanol and diethyl carbonate to obtain Boc protected 3-amino-2-oxazolidinone; and 4) performing deprotection on the Boc group in the Boc protected 3-amino-2-oxazolidinone to obtain 3-amino-2-oxazolidinone. According to the method, the yield of AOZ in the synthesis process is obviously increased, and separation and purification are facilitated.

CYCLIC HYDRAZIDES AS FRAGRANCE PRECURSOR COMPOUNDS

Fragrance precursor compounds of the formula (I) may be derived from hydrazides and fragrance aldehydes and ketones. The fragrance precursor compounds may be used in composition having washing or cleaning agents, cosmetic agents and air care agents. A method for long-lasting fragrancing of surfaces using the fragrance precursor compounds and agents is also disclosed.

Synthetic method of furazolidone metabolite AOZ

The invention discloses a preparation method of 3-amino-2-oxazolidinone (AOZ). The method comprises the following steps: 1) carrying out a reaction on ethylene glycol and PBr3 to obtain 2-bromoethanol; 2) carrying out a substitution reaction on 2-bromoethanol and an alkali, then adding hydrazine hydrate into the system, continuously carrying out a ring-opening reaction, and removing excessive 2-bromoethanol and water after the reaction is completed to obtain an intermediate 2-hydrazinoethanol; and 3) in the presence of an alkali, carrying out a reaction on 2-hydrazinoethanol and diethyl carbonate to obtain 3-amino-2-oxazolidinone (AOZ). According to the method, a nitrofuran metabolite AOZ is synthesized by adopting a one-pot method at the rear half part, so that the loss of a separated andpurified sample in the synthesis process is greatly reduced.

Design, synthesis, and biological evaluation of 3-amino-2-oxazolidinone derivatives as potent quorum-sensing inhibitors of Pseudomonas aeruginosa PAO1

Due to the increasing resistance of Pseudomonas aeruginosa to most clinically relevant antimicrobials, it is challenging to treat bacterial infection with traditional antibiotics. Quorum sensing can regulate the production of biofilms and virulence factors which are closely related to bacterial resistance. Previously we synthesized a series of oxazolidinone compounds targeting the quorum-sensing transcriptional regulatory protein CviR and ZS-12 showed good activity against Chromobacterium violaceum CV026 quorum-sensing. In this study, eighteen 3-amino-2-oxazolidinone compounds were designed and synthesized using ZS-12 as the lead compound. We initially evaluated the inhibitory activities of novel oxazolidinone compounds against QS using C. violaceum CV026 as a reporter strain. Thirteen compounds showed good activities (IC50 range 3.69–63.58 μM) and YXL-13 inhibition was the most significant (IC50 = 3.686 ± 0.5790 μM) against biofilm formation and virulence factors determination of P. aeruginosa PAO1. In vitro, YXL-13 significantly inhibited the formation of PAO1 biofilm (range 42.98%–17.67%), the production of virulence factors (pyocyanin, elastase, rhamnolipid, and protease), and bacterial motility. Moreover, the combination of YXL-13 with an antibiotic (meropenem trihydrate) could significantly improve the antibiotic susceptibility of biofilm P. aeruginosa PAO1 cells. In vivo, YXL-13 significantly prolonged the lifespan of wildtype Caenorhabditis elegans N2 infected by P. aeruginosa PAO1. In conclusion, YXL-13 is a candidate agent for antibiotic-resistant P. aeruginosa PAO1and provides a method for finding new antibacterial drugs.

Plant Uptake and Metabolism of Nitrofuran Antibiotics in Spring Onion Grown in Nitrofuran-Contaminated Soil

Environmental pollution caused by the discharge of mutagenic and carcinogenic nitrofurans to the aquatic and soil environment is an emerging public health concern because of the potential in producing drug-resistant microbes and being uptaken by food crops. Using liquid chromatography-tandem mass spectrometry analysis and with spring onion (Allium wakegi Araki) as the plant model, we investigated in this study the plant uptake and accumulation of nitrofuran from a contaminated environment. Our study revealed for the first time high uptake and accumulation rates of nitrofuran in the edible parts of the food crop. Furthermore, results indicated highly efficient plant metabolism of the absorbed nitrofuran within the plant, leading to the formation of genotoxic hydrazine-containing metabolites. The results from this study may disclose a previously unidentified human exposure pathway through contaminated food crops.

3-Aminooxazolidinone AHL analogs as hydrolytically-stable quorum sensing agonists in Gram-negative bacteria

Synthetic molecules that modulate quorum sensing, QS, in bacteria have great potential for use in synthetic biology applications as well as acting as anti-virulence and anti-biofilm agents. Acylhomoserine lactone (AHL)-based autoinducer analogs have been extensively developed as QS modulators but these suffer from both chemical and enzymatic degradations. Here, we reveal that 3-aminooxazolidinone acylhomoserine lactone analogs are hydrolytically stable and are as potent in activating LuxR-type receptors. Docking analysis revealed that 3-oxo-C12-3-aminooxazolidinone docked in LasR of P. aeruginosa, making similar interactions with the protein's active-site residues to the native ligand, 3-oxo-C12 HSL. Experimentally, 3-oxo-C12-3-aminooxazolidinone was equally as potent as the natural ligand in inducing bioluminescence in E. coli carrying a bioluminescent gene that was under the control of LasR. In C. violaceum CV026, the 3-aminooxazolidinone analogs could also modulate pigment (violacein) formation, albeit this time not as potent as the natural AHL ligands.

NOVEL BACTERIAL COLONY SENSING REGULATOR AND MEDICAL USE

The invention relates to a compound of formula I, and a preparation method and use thereof. The compound has a bacterial quorum-sensing regulatory effect, and can be used for prevention and/or treatment of a disease caused by a bacterial infection.

Catalytic enantioselective indium-mediated allylation of hydrazones

(Chemical Equation Presented) A facile and highly selective indium-mediated allylation of hydrazones utilizing BINOL ligands is described. Chiral (R)-3,3′-bistrifluoromethylBINOL afforded homoallylic amines in up to 97% ee with stoichiometric ligand. Employing only 10 mol % ligand afforded selectivity of up to 92% ee.