2-Oxazolidinone

changed 477215129 2-Oxazolidone 2-Oxazolidone structure.svg skin-invert-image Oxazolidin-2-one-3D-balls.png bg-transparent 1,3-Oxazolidin-2-one 1,3-Oxazolidin-2-one, 2-Oxo-1,3-oxazolidine, 2-Oxotetrahydro-1,3-oxazole O=C1OCCN1 correct kegg C06695 1/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5) IZXIZTKNFFYFOF-UHFFFAOYAE 73949 correct chemspider 1S/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5) correct chemspider IZXIZTKNFFYFOF-UHFFFAOYSA-N correct CAS 497-25-6 correct FDA Z4D49W92PP correct chemspider 66579 C3H5NO2 87.077 g/mol white or colorless solid 86 to 89 220 at 48 torr Oxazolidine 2-Oxazolidinone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring. Synthesis and occurrence The compound arises by the reaction of an ethanolamine and dimethylcarbonate10.15227/orgsyn.062.0149 free Synthesis and Diels–Alder Rearctions of 3-Acetyl-2(3H)-Oxazolone: 6-Amino-3,4-dimethyl-cis-3-cyclohexen-1-ol Organic Syntheses 1984 62 149 Karl-Heinz Scholz, Hans-Georg Heine, Willy Hartmann or related phosgene equivalents.10.15227/orgsyn.075.0045 free (4R,5S)-4,5-Diphenyl-3-Vinyl-2-Oxazolidinone Organic Syntheses 1998 75 45 T. Akiba, O. Tamura, S. Terashima It is one of waste products generated in amine gas treating due to cyclization of ethanolamine carbamate.Salim S. R. S. 2021-03-01 Treatment of amine wastes generated in industrial processes IOP Conference Series: Materials Science and Engineering 1092 1 012051 10.1088/1757-899x/1092/1/012051 1757-8981 free 2021MS&E.1092a2051S History The compound was first reported in 1888 by German chemist Siegmund Gabriel. While investigating reactions of bromoethylamine hydrobromide, he treated it with silver carbonate and isolated a product with melting point around 90–91°C. He determined its empirical formula correctly, but neither gave it a specific name nor studied its properties.Gabriel S. 1888 Ueber einige Derivate des Aethylamins https://books.google.com/books?id=d_1hofkLJ-wC&pg=PA568 Berichte der Deutschen Chemischen Gesellschaft de 21 1 566–575 10.1002/cber.188802101103 0365-9496 Nine years later Gabriel returned to the topic together with G. Eschenbach, developing a more efficient synthesis using sodium bicarbonate instead of the silver salt. They referred to the compound as "Oxäthylcarbaminsäureanhydrid" (hydroxyethylcarbamic acid anhydride), recognizing its relationship to ethanolamine and its cyclic structure. Their 1897 paper focused on optimizing the yield of oxazolidone and investigating some of its reactions, such as its conversion to 1-(2-hydroxyethyl)-3-phenylurea upon treatment with aniline.Gabriel S. Eschenbach G. September 1897 Notizen über Bromäthylamin und Vinylamin https://books.google.com/books?id=jAvVlrHhI1kC&pg=PA2494 Berichte der Deutschen Chemischen Gesellschaft de 30 3 2494–2497 10.1002/cber.18970300324 0365-9496 subscription Substituted oxazolidinones Evans auxiliaries Oxazolidinones are useful as Evans auxiliaries, which are of interest for chiral synthesis. In a common implementation, an acid chloride substrate reacts with a chiral 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.10.15227/orgsyn.068.0083 free Diastereoselective Aldol Condensation Using a Chiral Oxazolidinone Auxiliary: (2S,3S)-3-Hydroxy-3-Phenyl-2-Methylpropanoic Acid Organic Syntheses 1990 68 83 James R. Gage, David A. Evans Asymmetric Diels-Alder reactions are also enabled by these auxiliaries.10.15227/orgsyn.071.0030 free Enantioselective, Catlytic Diels-Alder Reaction: (1S-endo)-3-(Bicyclo[2.2.1]Hept-5-en-2-ylcarbonyl)-2-Oxazolidinone Organic Syntheses 1993 71 30 S. Pikul, E. J. Corey Pharmaceuticals Oxazolidinones are found in some antimicrobials. Oxazolidinones inhibit protein synthesis by interfering with the binding of N-formylmethionyl-tRNA to the ribosome. Shinabarger D. 10.1517/13543784.8.8.1195 Mechanism of action of the oxazolidinone antibacterial agents Expert Opinion on Investigational Drugs 8 8 1195–1202 1999 15992144 (See Linezolid#Pharmacodynamics) Some of the most important oxazolidinones are antibiotics.Antibiotics: Targets, Mechanisms and Resistance A Chemist's Survey of Different Antibiotic Classes Sonia Ilaria Maffioli Claudio O. Gualerzi Letizia Brandi Attilio Fabbretti Cynthia L. Pon 2014 Wiley-VCH 978-3-527-65968-5 Examples of oxazolidinone-containing antibiotics: Linezolid (Zyvox), which is available for intravenous administration and also has the advantage of having excellent oral bioavailability. Posizolid, which appears to have excellent, targeted bactericidal activity against all common gram-positive bacteria, regardless of resistance to other classes of antibiotics.Wookey, A. Turner, P. J. Greenhalgh, J. M. Eastwood, M. Clarke, J. Sefton, C. AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro Clinical Microbiology and Infection 2004 10 3 247–254 15008947 10.1111/j.1198-743X.2004.00770.x free thumb|250px|right|Chemical structure of tedizolid Tedizolid, (Sivextro) which is approved for acute skin infections Radezolid (RX-1741) has completed some phase-II clinical trials.http://www.rib-x.com/pipeline/rx_1741 Rx 1741 Rib-X Pharmaceuticals 2009 2009-05-17 https://web.archive.org/web/20090226201337/http://www.rib-x.com/pipeline/rx_1741 2009-02-26 Contezolid (MRX-I) has reported phase 1 data10.1021/jm401931e 57 11 New Potent Antibacterial Oxazolidinone (MRX-I) with an Improved Class Safety Profile 2014 Journal of Medicinal Chemistry 4487–4497 Gordeev Mikhail F. Yuan Zhengyu Y. 24694071 and phase III data. 10.1093/jac/dkac073 A Phase III multicentre, randomized, double-blind trial to evaluate the efficacy and safety of oral contezolid versus linezolid in adults with complicated skin and soft tissue infections 2022 Zhao Xu Huang Haihui Yuan Hong Yuan Zhengyu Zhang Yingyuan Journal of Antimicrobial Chemotherapy 77 6 1762–1769 35265985 In 2021, a new drug summary was published by ADIS Press. 10.1007/s40265-021-01576-0 Contezolid: First Approval 2021 Hoy Sheridan M. Drugs 81 13 1587–1591 34365606 8536612 In June 2021, marketing approval was granted by the Chinese National Medical Products Administration (NMPA) for use of oral contezolid in moderate to severe complicated skin and skin structure infections. http://www.micurx.com/703.html China NMPA Approves MicuRx's Contezolid for Treatment of Drug-Resistant Bacterial Infection – MicuRx Pharmaceuticals, Inc In June 2022, contezolid oral tablets and contezolid acefosamil IV (a prodrug of contezolid) began Phase 3 global clinical trials in moderate to severe diabetic foot infections.ClinicalTrials.gov Identifier: NCT05369052 An additional global Phase 3 study is planned for acute bacterial skin and skin structure infections (ABSSSI) for the combination of contezolid and contezolid acefosamil. An oxazolidinone derivative used for other purposes is rivaroxaban, which is approved by the U.S. FDA for venous thromboembolism prophylaxis. thumb|200px|right|Chemical structure of linezolid A first commercially available 1,3-oxazolidinone is the antibiotic linezolid. See also Oxazolidine – the ring without the carbonyl group Oxazolone – the unsaturated analogues References External links Synthesis of Oxazolidinones – Recent Literature Category:Oxazolidinones Category:2-Oxazolidinones