154590-62-2Relevant articles and documents
RETRACTED ARTICLE: Design, synthesis of novel oxazolidino-amides/sulfonamides conjugates and their impact on antibacterial activity
Bharath, Yarlagadda,Alugubelli, Gopi Reddy,Sreenivasulu, Reddymasu,Rao, Mandava. V. Basaveswara
, p. 457 - 468 (2018/02/09)
Abstract: In view of generating new compounds for future drug development, we have synthesized oxazolidinones library of aryl amides and aryl sulfonamide derivatives. These compounds were screened in vitro against panel of susceptible and resistant Gram-p
Synthesis and biological evaluation of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives
Phillips, Oludotun A.,D'Silva, Roselyn,Bahta, Teklu O.,Sharaf, Leyla H.,Udo, Edet E.,Benov, Ludmil,Eric Walters
, p. 120 - 131 (2015/11/24)
Research activities on the oxazolidinone antibacterial class of compounds continue to focus on developing newer derivatives with improved potency, broad-spectrum activity and safety profiles superior to linezolid. Among the safety concerns with the oxazolidinone antibacterial agents is inhibition of monoamine oxidases (MAO) resulting from their structural similarity with toloxatone, a known MAO inhibitor. Diverse substitution patterns at the C-5 position of the oxazolidinone ring have been shown to significantly affect both antibacterial activity and MAO inhibition to varying degrees. Also, the antibacterial activity of compounds containing iron-chelating functionalities, such as the hydroxamic acids, 8-hydroxyquinolines and catechols have been correlated to their ability to alter iron intake and/or metabolism. Hence a series of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives were synthesized and evaluated for their antibacterial and MAO-A and -B inhibitory activities. The compounds were devoid of significant antibacterial activity but most demonstrated moderate MAO-A and -B inhibitory activities. Computer modeling studies revealed that the lack of potent antibacterial activity was due to significant steric interaction between the hydroxamic acid N-OH oxygen atom and one of the G2540 5′-phosphate oxygen atoms at the bacterial ribosomal binding site. Therefore, the replacement of the 5-acetamidomethyl group of linezolid with the 5-(N-hydroxyacetamido)methyl group present in the hydroxamic acid oxazolidinone derivatives was concluded to be detrimental to antibacterial activity. Furthermore, the 5-(hydroxamic acid)methyl oxazolidinone derivatives were also less active as MAO-A and -B inhibitors compared with linezolid and the selective inhibitors clorgyline and pargyline. In general, the 5-(hydroxamic acid)methyl oxazolidinone derivatives demonstrated moderate but selective MAO-B inhibitory activity.
Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry
Yan, Shanshan,Miller, Marvin J.,Wencewicz, Timothy A.,Moellmann, Ute
supporting information; experimental part, p. 1302 - 1305 (2010/06/15)
A series of novel oxazolidinone antibiotics having [2.2.1] and [2.2.2] bicyclic oxazine moieties at the C-5 side chain of the A-ring was synthesized by nitroso Diels-Alder reactions, from three linezolid analogs containing morpholine, piperazine and thiomorpholine, respectively, as the C-ring components. Subsequent N-O bond cleavage generated oxazolidinones with 4-amino cyclo-2-en-1-ol substituents. The in vitro antibacterial activities of these oxazolidinone analogs were evaluated.
OXAZOLIDINONE DERIVATIVES AS ANTIMICROBIALS
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Page/Page column 50; 51, (2008/06/13)
The present invention relates to substituted phenyl oxazolidinones and processes for preparing thereof. This invention also relates to pharmaceutical compositions comprising compounds of the present invention. Such compounds can be useful antimicrobial ag
Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3-[4- (3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide (BAY 59-7939): An oral, direct factor Xa inhibitor
Roehrig, Susanne,Straub, Alexander,Pohlmann, Jens,Lampe, Thomas,Pernerstorfer, Josef,Schlemmer, Karl-Heinz,Reinemer, Peter,Perzborn, Elisabeth
, p. 5900 - 5908 (2007/10/03)
Despite recent progress in antithrombotic therapy, there is still an unmet medical need for safe and orally available anticoagulants. The coagulation enzyme Factor Xa (FXa) is a particularly promising target, and recent efforts in this field have focused on the identification of small-molecule inhibitors with good oral bioavailability. We identified oxazolidinone derivatives as a new class of potent FXa inhibitors. Lead optimization led to the discovery of BAY 59-7939 (5), a highly potent and selective, direct FXa inhibitor with excellent in vivo antithrombotic activity. The X-ray crystal structure of 5 in complex with human FXa clarified the binding mode and the stringent requirements for high affinity. The interaction of the neutral ligand chlorothiophene in the S1 subsite allows for the combination of good oral bioavailability and high potency for nonbasic 5. Compound 5 is currently under clinical development for the prevention and treatment of thromboembolic diseases.
Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid
Das, Biswajit,Rudra, Sonali,Yadav, Ajay,Ray, Abhijit,Raja Rao,Srinivas,Soni, Ajay,Saini, Suman,Shukla, Shalini,Pandya, Manisha,Bhateja, Pragya,Malhotra, Sunita,Mathur, Tarun,Arora,Rattan, Ashok,Mehta, Anita
, p. 4261 - 4267 (2007/10/03)
Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles.
NOVEL ANTIBACTERIAL AGENTS
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Page 32, (2010/02/06)
The present invention provides novel compounds of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and phar
