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1 ne enolate equivalent of 4-benzyl-N-glycinyl oxazolidinone".
2 h the aromatic ring directly attached to the oxazolidinone.
3 i-conjugating substituent is proximal to the oxazolidinone.
4 ative fashion, releasing each monomer as a 2-oxazolidinone.
5 lowed by efficient resolution using a chiral oxazolidinone.
6 -to-U mutation, also conferred resistance to oxazolidinone.
7 r insertion reaction to produce 5,5-dimethyl oxazolidinone.
8 ce is not blocked by the substituents on the oxazolidinone.
9 boron enolates to enals using the same Evans oxazolidinones.
10 ing expansion to a mixture of cis- and trans-oxazolidinones.
11 of Rh2(OAc)4, providing mannosamine 2-N,3-O-oxazolidinones.
12 onventional acetamide functionality found in oxazolidinones.
13 icant role in the mechanism of action of the oxazolidinones.
14 acterial peptides and a new class of agents, oxazolidinones.
15 of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones.
16 blocks: 4-oxazolin-2-ones and 4-methylene-2-oxazolidinones.
17 carbamates, thiocarbamates, hydantoins, and oxazolidinones.
18 ted together with isomerization rates of the oxazolidinones.
19 g pyridines, quinolines, pyrrolidinones, and oxazolidinones.
20 ty for 92 isolates tested) and linezolid, an oxazolidinone (100% susceptibility for 41 isolates teste
21 23 and 54, prepared from epoxy alcohol 9 via oxazolidinones 15 and 51, respectively, underwent ring-c
23 n anti-selective aldol addition of propionyl oxazolidinone 28 to angelic aldehyde 27, followed by a H
24 oxy)phenylmagnesium bromide and CuCN to acyl oxazolidinone 50 was developed (85% yield, only the requ
25 old were synthesized starting from Seebach's oxazolidinone 6 and were subsequently employed in asymme
35 ructural basis for the discovery of improved oxazolidinones active against emerging drug-resistant cl
36 Further functionalization of 4-methylene-2-oxazolidinones afforded substituted indoles and heterocy
37 actory for reaction of the chiral N-acylated oxazolidinone, affording (2S,3S)-2-(3-((tert-butyldiphen
39 tion of CuF(2)/DTBP-catalyzed N-arylation of oxazolidinones, amides, amines, and azoles has been expl
40 none (AOZ) and 3-amino-5-morpholino-methyl-2-oxazolidinone (AMOZ) side-chains of furazolidone and fur
41 lidinone (AOZ), 3-amino-5-morpholinomethyl-2-oxazolidinone (AMOZ), 1-aminohydantoine (AHD), semicarba
43 ith regard to the synthesis of antibacterial oxazolidinone analogues of the Zyvox antimicrobial famil
45 a potent survival advantage conferred by the oxazolidinone and called into question the use of glycop
47 of sialyl phosphates suggest that the 4O,5N-oxazolidinone and the 4,5-O-carbonate systems influence
48 in which the lactone ring is replaced by an oxazolidinone and the bridging methylene group is in the
49 iscrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazol
50 nyls in 0.5 mol % loading and N-arylation of oxazolidinones and amides with aryl iodides in 8 mol % l
52 in revealed partial cross-resistance between oxazolidinones and chloramphenicol; no cross-resistance
54 ends of the enamine formation rates from exo-oxazolidinones and endo-oxazolidinones upon variation of
56 ibacterial agents, collectively known as the oxazolidinones and exemplified by linezolid (PNU-100766,
59 fluences only the isomerization rates of the oxazolidinones and not the enamine formation rates, whic
63 and tertiary lactams, 2-imidazolidinones, 2-oxazolidinones, and succinimides) to the cumyloxyl radic
66 ring the course of our investigations in the oxazolidinone antibacterial agent area, we have identifi
67 of new nitrogen-carbon-linked (azolylphenyl)oxazolidinone antibacterial agents has been prepared in
73 osphate is the second commercially available oxazolidinone antibiotic, although the first one in clas
74 raocular injection of linezolid, a synthetic oxazolidinone antibiotic, was performed in rabbits to as
79 ites investigated were as follows: 3-amino-2-oxazolidinone (AOZ), 3-amino-5-morpholinomethyl-2-oxazol
85 antibacterial agents such as rifamycins and oxazolidinones are designed to overcome both quinolone-s
92 s a nucleophile-assisted anti elimination of oxazolidinones as a major enamine formation pathway.
93 of enamine formation and clarify the role of oxazolidinones as nonparasitic intermediates in proline
99 sing an oxyallyl containing a (R)-4-phenyl-2-oxazolidinone auxiliary (2(Ph)), under either thermal or
100 on of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocont
101 azones bearing different substituents on the oxazolidinone auxiliary were compared; consistently high
102 istribution depended on the structure of the oxazolidinone auxiliary, substituent on the enolate, and
103 R spectroscopic and computational studies of oxazolidinone-based lithium enolates-Evans enolates-in t
104 gy has also been applied to the synthesis of oxazolidinone-based marketed drugs, including Rivaroxaba
106 the discovery of an alternative mechanism of oxazolidinone-based stereocontrol that does not require
108 of N-acyl-imides, N-acyl-lactams, and N-acyl-oxazolidinones bearing five- and six-membered rings usin
112 The structure and exact location of the oxazolidinone binding site remain obscure, as does the m
113 A mutants G2032A and G2447A are resistant to oxazolidinones both in vitro and in vivo with the latter
114 rgies (BDE) of the complexed and uncomplexed oxazolidinone bromide suggest that complexation lowers t
115 pi-conjugating substituent is distal to the oxazolidinone but decreased steric interaction when the
117 m the E isomer of the oxyallyl (in which the oxazolidinone C horizontal lineO and oxyallyl oxygen are
118 catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of ti
119 functional groups--ester, epoxide, sulfone, oxazolidinone, carbamate, and sulfamate--are found to en
120 the erythronolide core provided a series of oxazolidinone carbamates that were equally as active as
122 y orientation such that in one conformer the oxazolidinone carbonyl is oriented toward the OH of the
123 substituted and terminal alkenes using Shi's oxazolidinone catalyst, the asynchronicity of the epoxid
124 ts of the type 2 IMDA reaction incorporating oxazolidinone chiral auxiliaries have been evaluated.
125 symmetric Diels-Alder reactions using Evans' oxazolidinone chiral auxiliary furnished a high level of
127 Linezolid, the first antimicrobial of the oxazolidinone class, has met with more widespread use an
129 dation of various styrenes using carbocyclic oxazolidinone-containing ketone 3 has been investigated.
130 f various olefins with an N-aryl-substituted oxazolidinone-containing ketone as catalyst and hydrogen
131 utyrolactones, using the N-tolyl-substituted oxazolidinone-containing ketone as catalyst and Oxone as
132 The chiral auxiliary, 4-diphenylmethyl-2-oxazolidinone, controlled the stereoselectivity in both
133 terial agents but, with the exception of the oxazolidinone core, no new scaffolds have emerged in the
134 and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hi
137 xcellent torquoselectivities obtained in the oxazolidinone-directed Nazarov cyclization suggest that
138 Steady-state kinetic analysis shows that oxazolidinones display a competitive inhibition pattern
139 onent of the ribosomal peptidyl transferase, oxazolidinones do not inhibit peptide bond formation, an
140 id tests during the clinical-trial phases of oxazolidinone drug development in order to ensure test a
143 or allylation of a silylenolate of an N-acyl oxazolidinone; excellent enantioselectivities and yields
144 ne derivatives that are incapable of forming oxazolidinones exhibit no rate enhancement in the presen
146 xycarbonylaryl isocyanates formed a bicyclic oxazolidinone, followed by a sequence of intramolecular
147 verted in a one pot manner to functionalized oxazolidinones following a regio- and stereoselective ox
149 eagents with nonracemic N-enoyl-4-phenyl-1,3-oxazolidinones for the preparation of 1,3-syn-dimethyl a
150 luoromethyl groups at the phenyl ring of the oxazolidinone fragment are the most potent in each serie
151 xploited to prepare more than 40 examples of oxazolidinones from a variety of aryl- and alkyl-substit
152 e-scale syntheses of 3-(cycloprop-2-en-1-oyl)oxazolidinones from acetylene and ethyl diazoacetate are
153 pecific synthesis of vicinally substituted 2-oxazolidinones from alpha,beta-unsaturated lactams using
154 C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported.
156 cular cross-coupling of N-aryl-4-methylene-2-oxazolidinones furnished a series of oxazolo[3,4-a]indol
160 renine substrate led to the discovery of the oxazolidinone GSK180 as a potent and specific inhibitor
161 metric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for th
163 stly, a method for the preparation of chiral oxazolidinone heterocycles from chiral epoxy alcohols is
164 razic acid 9 moieties were obtained by Evans oxazolidinone imide enolate alkylation and hydrazination
165 e free radical atom transfer reactions of an oxazolidinone imide substrate, 1, derived from alpha-bro
166 or clinical use include linezolid, the first oxazolidinone in clinical use, daptomycin, the first lip
168 ed enolization of (+)-4-benzyl-3-propionyl-2-oxazolidinone in THF-hydrocarbon mixtures shows unusual
170 erivatives to identify the site of action of oxazolidinones in the ribosomes of bacterial and human c
171 terial properties of a series of piperazinyl oxazolidinones in which the distal nitrogen of the piper
172 The antibiotics chloramphenicol (CHL) and oxazolidinones, including linezolid (LZD), are known to
178 utagenesis, and structural data suggest that oxazolidinones interfere with initiator fMet-tRNA bindin
179 orms an N-protonated enamine species from an oxazolidinone intermediate accounts for the experimental
180 raction between the bifunctional urea and an oxazolidinone intermediate to increase the rate of enami
184 ibenzothiphene sulfilimine confirms that the oxazolidinone is the major product with an estimated yie
185 This paper describes a new class of chiral oxazolidinone ketone catalyst for asymmetric epoxidation
188 tion, the crystal structure of the canonical oxazolidinone, linezolid, has been determined bound to t
189 deformylase inhibitors, and new lincosamide, oxazolidinone, lipopeptide and cephalosporin derivatives
191 etamide, pyrrolidinone, imidazolidinone, and oxazolidinone moieties at P2 are the most potent with K(
192 form a new chemotype by virtue of an unusual oxazolidinone moiety and exhibit specific antibiosis aga
193 The majority of the ligands incorporate the oxazolidinone moiety as a novel polar head, and the natu
194 s between the substituents on enynes and the oxazolidinone moiety of the ketone catalyst are importan
195 en the alkyne group of the substrate and the oxazolidinone moiety of the ketone catalyst as well as t
196 data were used to model the position of the oxazolidinone molecule within its binding site in the pe
197 prepared to explore the potential of these 4-oxazolidinone natural products as antimicrobial agents.
199 noglycosides, vancomycin, lipoglycopeptides, oxazolidinones, novel tetracycline-derivatives, and dapt
202 ed diastereotopic faces (by virtue of chiral oxazolidinone) of the enecarbamates exhibit distinct dif
204 oxazolidinones were converted separately to oxazolidinone-opened derivatives 28alpha and 28beta.
205 a-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines
206 e Evans syn aldol products using N-propionyl oxazolidinones, oxazolidinethiones, and thiazolidinethio
207 tionic species, weak nucleophiles such as NH-oxazolidinone participated efficiently in the hydroamina
210 e research in this area, the discovery of an oxazolidinone possessing improved myelotoxicity compared
213 aerobic oxidative amination of styrene with oxazolidinone proceeds with catalyst-controlled regiosel
216 It is demonstrated that a ring-fused 2,3-oxazolidinone-protected derivative of 1-tolylthio-N-acet
220 rived from commercially available 4-benzyl-2-oxazolidinone provide a rigid, conformationally restrict
224 tes with what is presently the most frequent oxazolidinone resistance mutation may aid surveillance a
225 sis in the wild-type rRNA operon produced an oxazolidinone resistance phenotype, establishing that th
226 me interaction, we selected Escherichia coli oxazolidinone-resistant mutants, which contained a rando
227 ydrazones with different substituents on the oxazolidinone revealed that benzyl and diphenylmethyl we
228 ammonia equivalents in the N-amination of 2-oxazolidinones revealed that O-(p-nitrobenzoyl)hydroxyla
229 state of 4pi electrocyclic ring closure, the oxazolidinone ring and the cyclizing pentadienyl cation
230 es and the N-acetyl substituent of the 2N,3O-oxazolidinone ring in stereochemical control is presente
231 enzyme complexes, the carbonyl group of the oxazolidinone ring makes hydrogenbond interactions with
232 e leverage the tunability of oxazolidine and oxazolidinone rings to systematically characterize struc
233 es of N-acetylglucosamine, protected with an oxazolidinone spanning the nitrogen and O-3, and bearing
235 higher levels of allylic strain between the oxazolidinone substituent and adjacent groups on the pen
240 microbial susceptibility testing showed that oxazolidinones such as linezolid (mean MIC 3.13 mug/mL)
241 powerful electron-withdrawing nature of the oxazolidinone system, which in turn is a function of its
242 can be extended to include the synthesis of oxazolidinone systems through use of dimethyl carbonate.
244 exposure to amikacin and the next-generation oxazolidinone tedizolid (both target ribosomes) or cefox
248 macrolides (cethromycin and solithromycin), oxazolidinones (tedizolid phosphate and radezolid), and
251 The proposed isomeric dipeptide ion is an oxazolidinone that takes fully covalent and ion-neutral
255 here X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochira
258 study of a strategically designed library of oxazolidinones to determine the effects of molecular str
259 ddition of titanium(IV) enolates from N-acyl oxazolidinones to TEMPO has permitted us to suggest an e
260 of a new class of antimicrobial agents, the oxazolidinones, to be approved for clinical use in the U
262 ide, a dihydrofolate reductase inhibitor, an oxazolidinone, two peptide antibiotics, a glycylcycline,
268 ation rates from exo-oxazolidinones and endo-oxazolidinones upon variation of the proline and water c
269 yst efficiently transforms amino alcohols to oxazolidinones (upon reaction with CO(2) ) and then to m
270 lly 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and al
272 ent method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of
273 o-1-phenyl-1,3-dienes from a range of chiral oxazolidinones using palladium-catalysis is reported.
274 as allowed to react with N-triphenylmethyl-5-oxazolidinone via the corresponding azomethine ylide.
276 ymmetric alkylation using N-(N-Boc-glycinyl) oxazolidinone was standardized to ensure the stereoselec
279 d (Z)-enolate of (4S/4R)-4-benzyl-N-glycinyl oxazolidinones was extended following other subsequent r
280 tivity relationships of structurally related oxazolidinones, we have prepared and evaluated the antib
281 chiral reference, and the analyte 4-benzyl-2-oxazolidinone were generated by electrospray ionization
282 n-pentenyl glycosides of N-Cbz 2-mannosamine oxazolidinones were converted separately to oxazolidinon
284 tion of bacterial ribosomes predicts that if oxazolidinones were engineered to accumulate in Gram-neg
289 ads to increased steric interaction with the oxazolidinone when a pi-conjugating substituent is dista
290 ting adduct underwent cyclization to give an oxazolidinone, which could be readily hydrolyzed to an o
291 buted in part to the tied back nature of the oxazolidinone, which reduces hindrance around the nucleo
292 amine formation is zero-order in proline and oxazolidinones, which excludes the direct deprotonation
299 olone, nitroimidazole, diarylquinolines, and oxazolidinones), with 2965 relapse and 1544 colony-formi
300 computations, suggesting that valine-derived oxazolidinones would be superior to the phenylalanine-de