| 词条 | 2-Oxazolidone |
| 释义 |
| Watchedfields = changed | verifiedrevid = 477215129 | Name = 2-Oxazolidone | ImageFileL1 = 2-Oxazolidone structure.svg | ImageFileR1 = Oxazolidin-2-one-3D-balls.png | ImageName = | IUPACName = 1,3-Oxazolidin-2-one | OtherNames = 2-Oxazolidone 2-Oxazolidinone |Section1={{Chembox Identifiers | SMILES = O=C1OCCN1 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C06695 | InChI = 1/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5) | InChIKey = IZXIZTKNFFYFOF-UHFFFAOYAE | PubChem = 73949 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = IZXIZTKNFFYFOF-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 497-25-6 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 66579 | RTECS = |Section2={{Chembox Properties | Formula = C3H5NO2 | MolarMass = 87.077 g/mol | Appearance = Solid | Density = | Solubility = | MeltingPtC = 86 to 89 | BoilingPtC = 220 | BoilingPt_notes = at 48 torr | pKa = | pKb = |Section3={{Chembox Structure | CrystalStruct = | Dipole = |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = | FlashPt = | RPhrases = | SPhrases = |Section8={{Chembox Related | OtherCompounds = Oxazolidine }} 2-Oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring. OxazolidinonesEvans auxiliariesOxazolidinones are a class of compounds containing 2-oxazolidone in the structure. In chemistry, they are useful as Evans auxiliaries, which are used for chiral synthesis. Usually, the acid chloride substrate reacts with the oxazolidinone to form an imide. Substituents at the 4 and 5 position of the oxazolidinone direct any aldol reaction to the alpha position of the carbonyl of the substrate. PharmaceuticalsOxazolidinones are mainly used as antimicrobials. The antibacterial effect of oxazolidinones is by working as protein synthesis inhibitors, targeting an early step involving the binding of N-formylmethionyl-tRNA to the ribosome.[1] (See Linezolid#Mechanism of action) Some of the most important oxazolidinones are antibiotics.[2] Examples of antibiotic oxazolidinones include:
An oxazolidinone derivative used for other purposes is rivaroxaban, which is approved by the FDA for venous thromboembolism prophylaxis. HistoryDeveloped during the nineties when several bacterial strains were becoming resistant against such antibiotics as vancomycin. Linezolid (Zyvox) is the first approved agent in the class (FDA approval April 2000). {{clear|left}}The first commercially available 1,3-oxazolidinone antibiotic was linezolid, discovered and developed by Pharmacia & Upjohn. In 2002 AstraZeneca introduced{{clarify|date=October 2016}} posizolid (AZD2563). See also
References1. ^{{Cite journal | last1 = Shinabarger | first1 = D. | doi = 10.1517/13543784.8.8.1195 | title = Mechanism of action of the oxazolidinone antibacterial agents | journal = Expert Opinion on Investigational Drugs | volume = 8 | issue = 8 | pages = 1195–1202 | year = 1999 | pmid = 15992144}} 2. ^{{cite book|title=Antibiotics: Targets, Mechanisms and Resistance|chapter=A Chemist’s Survey of Different Antibiotic Classes|author=Sonia Ilaria Maffioli|editors = Claudio O. Gualerzi, Letizia Brandi, Attilio Fabbretti, Cynthia L. Pon|year=2014|publisher=Wiley-VCH|isbn=9783527659685}} 3. ^{{cite journal |author1=Wookey, A. |author2=Turner, P. J. |author3=Greenhalgh, J. M. |author4=Eastwood, M. |author5=Clarke, J. |author6=Sefton, C. | title = AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro | journal = Clinical Microbiology and Infection | year = 2004 | volume = 10 | issue = 3 | pages = 247–254 | pmid=15008947 | doi = 10.1111/j.1198-743X.2004.00770.x}} 4. ^{{cite web|url=http://www.rib-x.com/pipeline/rx_1741 |title=Rx 1741 |publisher=Rib-X Pharmaceuticals |year=2009 |accessdate=2009-05-17 |deadurl=yes |archiveurl=https://web.archive.org/web/20090226201337/http://www.rib-x.com/pipeline/rx_1741 |archivedate=2009-02-26 |df= }} 5. ^{{cite journal|doi=10.1021/jm401931e | volume=57 | issue=11 | title=New Potent Antibacterial Oxazolidinone (MRX-I) with an Improved Class Safety Profile | year=2014 | journal=Journal of Medicinal Chemistry | pages=4487–4497 | last1 = Gordeev | first1 = Mikhail F. | last2 = Yuan | first2 = Zhengyu Y.}} 6. ^MicuRx Initiates Phase 3 Clinical Trial for MRX-I... 2016 7. ^A. W. Frahm, H. H. J. Hager, F. v. Bruchhausen, M. Albinus, H. Hager: Hagers Handbuch der pharmazeutischen Praxis: Folgeband 4: Stoffe A-K., Birkhäuser, 1999, {{ISBN|978-3-540-52688-9}} External links
2 : Articles with validated CAS Registry Numbers|Oxazolidinones |
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