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Relevant bibliographies by topics / Synthesis of oxazolidinones

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Academic literature on the topic 'Synthesis of oxazolidinones'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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Journal articles on the topic "Synthesis of oxazolidinones"

1

Aoki, Hiroyuki, Lizhu Ke, Susan M. Poppe, et al. "Oxazolidinone Antibiotics Target the P Site on Escherichiacoli Ribosomes." Antimicrobial Agents and Chemotherapy 46, no. 4 (2002): 1080–85. http://dx.doi.org/10.1128/aac.46.4.1080-1085.2002.

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ABSTRACT The oxazolidinones are a novel class of antimicrobial agents that target protein synthesis in a wide spectrum of gram-positive and anaerobic bacteria. The oxazolidinone PNU-100766 (linezolid) inhibits the binding of fMet-tRNA to 70S ribosomes. Mutations to oxazolidinone resistance in Halobacterium halobium, Staphylococcus aureus, and Escherichia coli map at or near domain V of the 23S rRNA, suggesting that the oxazolidinones may target the peptidyl transferase region responsible for binding fMet-tRNA. This study demonstrates that the potency of oxazolidinones corresponds to increased

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McKee, E. E., M. Ferguson, A. T. Bentley, and T. A. Marks. "Inhibition of Mammalian Mitochondrial Protein Synthesis by Oxazolidinones." Antimicrobial Agents and Chemotherapy 50, no. 6 (2006): 2042–49. http://dx.doi.org/10.1128/aac.01411-05.

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ABSTRACT The effects of a variety of oxazolidinones, with different antibacterial potencies, including linezolid, on mitochondrial protein synthesis were determined in intact mitochondria isolated from rat heart and liver and rabbit heart and bone marrow. The results demonstrate that a general feature of the oxazolidinone class of antibiotics is the inhibition of mammalian mitochondrial protein synthesis. Inhibition was similar in mitochondria from all tissues studied. Further, oxazolidinones that were very potent as antibiotics were uniformly potent in inhibiting mitochondrial protein synthes

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3

Sangita, Km, Geeta Gupta, Anita Pandey, and Peetam Singh. "Oxazolidinones: Mechanism of action and molecular characterization of resistance mechanisms in staphylococci." Journal of Medical Society 39, no. 1 (2025): 15–21. https://doi.org/10.4103/jms.jms_156_24.

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ABSTRACT Oxazolidinones are a new class of antibiotics effective in treating infections caused by various Gram-positive bacteria including methicillin-resistant staphylococci and vancomycin-resistant enterococci. Linezolid, the first oxazolidinone available, has become a valuable clinical option for treating infections due to multidrug-resistant Gram-positive bacteria. It has been used for patients with bacteremia, osteomyelitis, endocarditis, and skin and soft tissue infections, particularly when other therapies failed. Oxazolidinones inhibit the initiation of protein synthesis by specificall

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Nagiec, Eva E., Luping Wu, Steve M. Swaney, et al. "Oxazolidinones Inhibit Cellular Proliferation via Inhibition of Mitochondrial Protein Synthesis." Antimicrobial Agents and Chemotherapy 49, no. 9 (2005): 3896–902. http://dx.doi.org/10.1128/aac.49.9.3896-3902.2005.

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ABSTRACT The oxazolidinones are a relatively new structural class of antibacterial agents that act by inhibiting bacterial protein synthesis. The oxazolidinones inhibit mitochondrial protein synthesis, as shown by [35S]methionine incorporation into intact rat heart mitochondria. Treatment of K562 human erythroleukemia cells with the oxazolidinone eperezolid resulted in a time- and concentration-dependent inhibition of cell proliferation. The cells remained viable, but an increase in doubling time was observed with eperezolid treatment. Inhibition was reversible, since washing and refeeding of

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5

Foti, Claudia, Anna Piperno, Angela Scala, and Ottavia Giuffrè. "Oxazolidinone Antibiotics: Chemical, Biological and Analytical Aspects." Molecules 26, no. 14 (2021): 4280. http://dx.doi.org/10.3390/molecules26144280.

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This review covers the main aspects concerning the chemistry, the biological activity and the analytical determination of oxazolidinones, the only new class of synthetic antibiotics advanced in clinical use over the past 50 years. They are characterized by a chemical structure including the oxazolidone ring with the S configuration of substituent at C5, the acylaminomethyl group linked to C5 and the N-aryl substituent. The synthesis of oxazolidinones has gained increasing interest due to their unique mechanism of action that assures high antibiotic efficiency and low susceptibility to resistan

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Swaney, Steve M., Hiroyuki Aoki, M. Clelia Ganoza, and Dean L. Shinabarger. "The Oxazolidinone Linezolid Inhibits Initiation of Protein Synthesis in Bacteria." Antimicrobial Agents and Chemotherapy 42, no. 12 (1998): 3251–55. http://dx.doi.org/10.1128/aac.42.12.3251.

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ABSTRACT The oxazolidinones represent a new class of antimicrobial agents which are active against multidrug-resistant staphylococci, streptococci, and enterococci. Previous studies have demonstrated that oxazolidinones inhibit bacterial translation in vitro at a step preceding elongation but after the charging ofN-formylmethionine to the initiator tRNA molecule. The event that occurs between these two steps is termed initiation. Initiation of protein synthesis requires the simultaneous presence of N-formylmethionine-tRNA, the 30S ribosomal subunit, mRNA, GTP, and the initiation factors IF1, I

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Siddaraj, Ranjith, Shivaraja Govindaiah, Raghu Ningegowda, Nanjunda Swamy Shivananju, and Babu Shubha Priya. "A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid." European Journal of Chemistry 9, no. 4 (2018): 353–59. http://dx.doi.org/10.5155/eurjchem.9.4.353-359.1783.

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A concise and efficient synthesis of linezolid and eperezolid were accomplished through a convergent scheme utilizing diverse reaction conditions. The synthesis demonstrates utility of a new approach to facilitate the expeditious construction of 3-aryl-5-(substituted methyl)-2-oxazolidinones and easier insertion of N-acetyl group. This new approach offers the possibility of accessing related 2-oxazolidinone members easily as well as making additional analogues of Linezolid. The adopted method afforded high purity and excellent yield compared to other existing synthetic methods. The compounds w

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Zadsirjan, Vahideh, and Majid M. Heravi. "Oxazolidinones as Chiral Auxiliaries in the Asymmetric 1,4-Conjugate Addition Reaction Applied to the Total Synthesis of Natural Products: A Supplemental Mini-Review." Current Organic Synthesis 15, no. 1 (2018): 3–20. http://dx.doi.org/10.2174/1570179414666170601115831.

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Background: The most frequently used chiral auxiliaries, oxazolidinones (Evans' oxazolidinones) have been employed in 1,4-congugate addition reactions to α,β-unsaturated carbonyl compounds. Supplementary to our previous reports in this mini-review, we attempted to underscore the applications of this strategy in a step (steps) in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Objective: In this mini-review, we try to underscore the applications of oxazolidinones (Evans’ oxazolidinones) in 1,4-congugate addition reactions to α,β-unsaturated ca

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Pi, Shao-Feng, Yue-Meng Guo, Zheng-Rui Zhou, Han-zhou Sun, and Bing Yi. "Synthesis of N-substituted-4-methylene-oxazolidinones via base-catalyzed cyclization of propargylic alcohols with p-toluenesulfonyl isocyanate." Journal of Chemical Research 44, no. 9-10 (2020): 521–23. http://dx.doi.org/10.1177/1747519820907304.

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A practical method is developed for the synthesis of oxazolidinone derivatives, an important class of heterocyclic compounds. The effect of bases and solvents on this cyclization reaction is discussed and a simple new base–solvent system (triethylamine in toluene) is found to be the most effective. The reaction conditions developed here are mild and no by-products are observed. Moreover, using optimized conditions, a number of differently substituted propargylic alcohols are cyclized to the corresponding N-substituted-4-methylene-oxazolidinones in yields of up to 99%.

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Schwarz, Jacob, and Kaitlyn Weeber. "Synthesis of Cyanoacetyl Oxazolidinones." Synthesis 44, no. 13 (2012): 1993–96. http://dx.doi.org/10.1055/s-0031-1291123.

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Dissertations / Theses on the topic "Synthesis of oxazolidinones"

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Phung, Chau V. "The Synthesis of Oxazolidinones from Aziridines and Carbon Dioxide." University of Cincinnati / OhioLINK, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1470741529.

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Ho, Hoi Tong Lawrence. "New methods in chiral synthesis." Thesis, University of Bath, 1999. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.301557.

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Zheng, Zilong. "Synthesis of Oxazolidinone Derivatives and Anti-Influenza Agents." Ohio University / OhioLINK, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1470739369.

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Orac, Crina M. "Stereochemical Synthesis of Ring E Analogs of Methyllycaconitine and 4,5-Disubstituted Oxazolidinones." Ohio University / OhioLINK, 2009. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1258046479.

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Ella-Menye, Jean-Rene. "Synthesis of Novel Chiral Heterocyclic Compounds for Antibacterial Agents and Peptidomimetics." ScholarWorks@UNO, 2007. http://scholarworks.uno.edu/td/611.

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Small chiral molecules are very important building blocks in the synthesis of biologically active compounds. These building blocks include nitrogen and oxygen-containing heterocycles such as 2-oxazolidinones, 1,3-oxazinan-2-ones, 2-oxazolines, oxazines, morpholine and morpholinones. Because of their interesting properties, chiral heterocycles have stirred great interest in the synthetic chemist community to develop useful and efficient strategies to these molecules. In this dissertation, the design and syntheses of various heterocyclic building blocks are presented, as well as the testing of t

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Revell, Kevin David. "Mode of action and structure-activity studies of N-alkylthio beta-lactams and N-alkylthio-2-oxazolidinones, and synthesis of second-generation disulfide Inhibitors of beta-Ketoacyl-Acyl Carrer Protein Synthase III (FabH) as potent antibacterial agents." [Tampa, Fla] : University of South Florida, 2006. http://purl.fcla.edu/usf/dc/et/SFE0001453.

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Fang, Fang. "Synthesis of Bicyclic and Tricyclic Analogues of Oxazolidinone." Ohio University / OhioLINK, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1357312054.

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Karmakar, S. "Synthetic studies towards pseudotheonamides, herbarium III, bicyclic thiohydantoins and oxazolidinone -5- one." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2006. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/2479.

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Bhandare, Richie R. "Investigation into the bioisosteric approach in the design, synthesis and evaluation of muscarinic receptor ligands." Diss., Temple University Libraries, 2013. http://cdm16002.contentdm.oclc.org/cdm/ref/collection/p245801coll10/id/214985.

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Pharmaceutical Sciences<br>Ph.D.<br>The acetylcholine (ACh) receptor system belongs to rhodopsin GPCR family and is an integral membrane protein divided into two types: muscarinic and nicotinic. The naturally occurring neurotransmitter acetylcholine binds to these two receptor systems non- selectively. The regulatory effects of the neurotransmitter acetylcholine are diverse ranging from autonomic nervous system and the central nervous system through different types of neurons innervated by cholinergic inputs. Muscarinic acetylcholine receptors (mAChRs) are divided into five receptor subtypes (

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Zhang, Jianjun. "Library Synthesis of Anticancer and Antibacterial Agents via Azide Chemistry." DigitalCommons@USU, 2010. https://digitalcommons.usu.edu/etd/711.

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Various anticancer and antibacterial agents have been synthesized via azide chemistry by taking advantage of carbohydrate. Starting from the synthesis of 14 glycosyl azides, a library of carbohydrate-oxazolidinone conjugates and a library of carbohydrate-cyclopamine conjugates with biological interests were synthesized based on a highly efficient "click reaction" assisted by sonication. Some of the conjugates have improved solubility and enhanced anticancer activity. A library of neomycin B derivatives with various modifications at the 5" position has been synthesized. Two leads exhibit

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Book chapters on the topic "Synthesis of oxazolidinones"

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Doustkhah, Esmail, and Fatemeh Majidi Arlan. "Synthesis of Bioactive Thioxoimidazolidinones, Oxazolidinones, Thioxothiazolidinones, Thiazolidinediones." In N-Heterocycles. Springer Nature Singapore, 2022. http://dx.doi.org/10.1007/978-981-19-0832-3_13.

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2

Wollenburg, Marco. "Synthese chiraler 2-Oxazolidinone." In Neuartige Carbenliganden für die selektive Hydrierung von Aromaten. Springer Fachmedien Wiesbaden, 2018. http://dx.doi.org/10.1007/978-3-658-24608-2_2.

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Barbachyn, Michael R., Steven J. Brickner, Robert C. Gadwood, et al. "Design, Synthesis, and Evaluation of Novel Oxazolidinone Antibacterial Agents Active Against Multidrug-Resistant Bacteria." In Resolving the Antibiotic Paradox. Springer US, 1998. http://dx.doi.org/10.1007/978-1-4615-4897-3_12.

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4

Unger, Thomas A. "Oxazolidines oxazolidinones oxazolidinediones oxazoles." In Pesticide Synthesis Handbook. Elsevier, 1996. http://dx.doi.org/10.1016/b978-081551401-5.50381-6.

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5

Taber, Douglass. "The Zakarian Synthesis of ( + )-Pinnatoxin A." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0097.

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( + )-Pinnatoxin A 3, isolated from the shellfish Pinna muricata, is thought to be a calcium channel activator. A key transformation in the synthesis of 3 reported (J. Am. Chem. Soc . 2008, 130, 3774) by Armen Zakarian, now at the University of California, Santa Barbara, was the diastereoselective Claisen rearrangement of 1 to 2. The alcohol portion of ester 1 was derived from the aldehyde 4, prepared from D-ribose. The absolute configuration of the secondary allylic alcohol was established by chiral amino alcohol catalyzed addition of diethyl zinc to the unsaturated aldehyde 5. The acid porti

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Taber, Douglass. "Best Synthetic Methods: Carbon-Carbon Bond Construction." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0018.

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In the context of peptidyl ketone synthesis, Troels Skrydstrup of the University of Aarhus developed (J. Org. Chem. 2008, 73, 1088) the elegant SmI2-mediated conjugate addition of acyl oxazolidinones such as 1 to acceptors such as 2. Sadagopan Raghavan of the Indian Institute of Chemical Technology, Hyderabad reported (Tetrahedron Lett. 2008, 49, 1601) that the addition of a Pummerer intermediate, generated by exposure of 4 to TFAA, to the terminal alkene 5 and SnCl4 led to efﬁcient C-C bond formation, to give the sulﬁde 6 as a single (unassigned) diastereomer. Pd-catalyzed carbonylation of ar

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DeRosa, Thomas F. "Oxazolidinones." In Advances in Synthetic Organic Chemistry and Methods Reported in US Patents. Elsevier, 2006. http://dx.doi.org/10.1016/b978-008044474-1/50064-5.

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Rudge, A. J., I. Collins, A. B. Holmes, and R. Baker,. "Enantioselective Synthesis of Deoxynojirimycin." In Exercises in Synthetic Organic Chemistry. Oxford University PressOxford, 1997. http://dx.doi.org/10.1093/oso/9780198559443.003.0061.

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Abstract Discussion Points What should the absolute sterechemistry of the oxazolidinone benzyl group of compound 1 be in order to furnish the required product 2 under the conditions reported? Suggest a structure for compound 6. Rationalise the stereoselectivity observed in step g. What is the mechanism of the Martin sulfurane step k leading to compound 11?

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Taber, Douglass F. "The Smith Synthesis of (−)-Calyciphylline N." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0095.

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The Daphniphyllum alkaloids are a diverse group, some of which exhibit potent biological activity. Amos B. Smith III of the University of Pennsylvania envisioned (J. Am. Chem. Soc. 2014, 136, 870) the preparation of the bicyclo[2.2.2] core of (−)-calyciphylline N 3 by the intramolecular Diels–Alder cyclization of 1 to 2, with the silicon of 2 a surrogate for the secondary alcohol of 3. Following the precedent of Mori (Tetrahedron Asymm. 2005, 16, 685), the requisite secondary center of 1 was set by methylation of the anion derived from the Evans acyl oxazolidinone 4. Reductive removal of the

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Link, J. T., S. Raghavan, and S. J. Danishefsky,. "Total Synthesis of Staurosporine." In Exercises in Synthetic Organic Chemistry. Oxford University PressOxford, 1997. http://dx.doi.org/10.1093/oso/9780198559443.003.0072.

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Abstract Discussion Points What is the structure of the intermediate formed in step d? Suggest a reason for the closure of the oxazoline ring on the 8-face (formation of 4) and not on the a-face. Step j yielded a 2.5:1 mixture of a.:8 epoxides. Give reasons for the low stereoselectivity observed. The minor epoxide was found to react less efficiently with 2. Suggest a possible reason for this observation. The Boe protecting group on the oxazolidinone nitrogen of 10 plays a crucial role in steps x and y. Suggest the reason why it was introduced. What is the mechanism of step c’?

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Conference papers on the topic "Synthesis of oxazolidinones"

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EASTER, JOHN A., EDWARD H. CHEW, and RICHARD S. P. HSI. "SYNTHESIS OF SEVERAL ANALOGUES OF A NEW CLASS OF SYNTHETIC ANTIBACTERIALS, OXAZOLIDINONES, RADIOLABELED WITH CARBON-14, AND TRITIUM AND STABLELABELED WITH CARBON-13 AND DEUTERIUM." In Proceedings of the 3rd International Conference on Isotopes. WORLD SCIENTIFIC, 2000. http://dx.doi.org/10.1142/9789812793867_0083.

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2

Gharib, Ali, Mina Roshani, and Manouchehr Jahangir. "Catalyzed N-acylation of carbamates and oxazolidinones by Heteropolyacids (HPAs)." In The 13th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2009. http://dx.doi.org/10.3390/ecsoc-13-00170.

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Eames, Jason, Gregory Coumbarides, Marco Dingjan, Tony Flinn, Northern Northen, and Yonas Yohannes. "Probing the Parallel Kinetic Resolution of Racemic Oxazolidinones using Quasi-enantiomeric Profens." In The 10th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2006. http://dx.doi.org/10.3390/ecsoc-10-01417.

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