Heterocyclic Building Blocks-Oxazolidine

On September 7, 2007, Beddow, James E.; Davies, Stephen G.; Ling, Kenneth B.; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Thomson, James E. published an article.SDS of cas: 168297-86-7 The title of the article was Asymmetric synthesis of β2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives. And the article contained the following:

Conjugate addition of lithium dibenzylamide to the SuperQuat derivative (S)-3-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one (derived from L-valine) and alkylation of the resultant lithium β-amino enolate provide, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yields and high enantiomeric excesses. Alternatively, conjugate addition of a range of secondary lithium amides to (S)-3-(2-alkylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives, diastereoselective protonation with 2-pyridone, and subsequent deprotection furnish a range of (R)-2-alkyl- and (R)-2-aryl-3-aminopropanoic acids in good yields and high enantiomeric excesses. Addnl., the boron-mediated aldol reaction of β-amino N-acyloxazolidinones is a highly diastereoselective method for the synthesis of a range of β-amino-β’-hydroxy N-acyloxazolidinones. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).SDS of cas: 168297-86-7

The Article related to alkylaminopropanoic acid preparation conjugate addition alkylation, superquat derivative conjugate addition alkylation, oxazolidinone amino hydroxy acyl preparation, asym synthesis beta amino acid and other aspects.SDS of cas: 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Montagnat, Oliver D.; Lessene, Guillaume; Hughes, Andrew B. published an article in 2010, the title of the article was Synthesis of Azide-alkyne Fragments for ‘Click’ Chemical Applications. Formation of Chiral 1,4-Disubstituted-(β-alkyl)-γ-1,2,3-triazole Scaffolds from Orthogonally Protected Chiral β-Alkyl-trialkylsilyl-γ-pentynyl Azides and Chiral β-Alkyl-γ-pentynyl-alcohols.Name: (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one And the article contains the following content:

A library of chiral γ-pentynyl alcs., I, and γ-pentynyl azides, e.g. II, was made using the SuperQuat chiral oxazolidin-2-one auxiliary. Coupling of the free alkynes with the azides by Huisgen 1,3-dipolar cycloaddition provided chiral oligomeric 1,4-disubstituted-1,2,3-triazoles, e.g. III, as possible peptidomimetic compounds The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Name: (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

The Article related to asym alkylation chiral auxiliary pentynyl alc azide preparation, huisgen dipolar cycloaddition chiral pentynyl alc azide reactant, click chem disubstituted triazole preparation pentynyl alc azide reactant and other aspects.Name: (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On December 1, 2019, Cao, Hengyi; Zhu, Guangya; Sun, Lin; Chen, Ge; Ma, Xinxin; Luo, Xiao; Zhu, Jidong published an article.Formula: C8H15NO2 The title of the article was Discovery of new small molecule inhibitors targeting isocitrate dehydrogenase 1 (IDH1) with blood-brain barrier penetration. And the article contained the following:

Isocitrate dehydrogenase 1 (IDH1), which catalyzes the conversion of isocitrate to α-ketoglutarate, is one of key enzymes in the tricarboxylic acid cycle (TCA). Hotspot mutation at Arg132 in IDH1 that alters the function of IDH1 by further converting the α-ketoglutarate(α-KG) to 2-hydroxyglutarate (2-HG) have been identified in a variety of cancers. Because the IDH1 mutations occur in a significant portion of gliomas and glioblastomas, it is important that IDH1 inhibitors have to be brain penetrant to treat IDH1-mutant brain tumors. Here we report the efforts to design and synthesize a novel serial of mutant IDH1 inhibitors with improved activity and the blood-brain barrier (BBB) penetration. We show that compound 5, (R)-4-((S)-1-fluoroethyl)-3-(2-(((S)-1-(7-(trifluoromethyl)4,5-dihydroimidazo[1,5-a]quinolin-3-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one [2379528-08-0], exhibits good brain exposure and potent 2-HG inhibition in a HT1080-derived mouse xenograft model, which makes it a potential preclin. candidate to treat IDH1-mutant brain tumors. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Formula: C8H15NO2

The Article related to glioblastoma antitumor pharmacokinetics isocitrate dehydrogenase 1 blood brain barrier, acute myeloid leukemia, blood-brain barrier, cancer therapy, glioblastoma, isocitrate dehydrogenase 1, small molecule inhibitors and other aspects.Formula: C8H15NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On September 19, 2005, Jones, Simon; Selitsianos, Dimitrios published an article.Product Details of 168297-86-7 The title of the article was Stereochemical consequences of the use of chiral N-phosphoryl oxazolidinones in the attempted kinetic resolution of bromomagnesium alkoxides. And the article contained the following:

A number of chiral N-phosphoryl oxazolidinones, e.g. I (R = H, Ph, R1 = CH2Ph; R = Me, R1 = CHMe2), have been prepared and evaluated as asym. phosphoryl transfer agents with the magnesium alkoxide of 1-phenylethanol. The reaction proceeded with little stereoselection, which was shown to be a consequence of the reaction mechanism that occurs with inversion of configuration at phosphorus consistent with in-line attack opposite the leaving group. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Product Details of 168297-86-7

The Article related to failed kinetic resolution secondary alc chiral phosphoryloxazolidinone, chiral phosphoryloxazolidinone failed kinetic resolution secondary alkoxide, oxazolidinone phosphoryl failed kinetic resolution secondary alkoxide and other aspects.Product Details of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On November 3, 2004, Burke, Martin D.; Berger, Eric M.; Schreiber, Stuart L. published an article.Formula: C8H15NO2 The title of the article was A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially. And the article contained the following:

The efficient synthesis of small mols. having many mol. skeletons is an unsolved problem in diversity-oriented synthesis (DOS). We describe the development and application of a synthesis strategy that uses common reaction conditions to transform a collection of similar substrates into a collection of products having distinct mol. skeletons. The substrates have different appendages that pre-encode skeletal information, called σ-elements. This approach is analogous to the natural process of protein folding in which different primary sequences of amino acids are transformed into macromols. having distinct three-dimensional structures under common folding conditions. Like σ-elements, the amino acid sequences pre-encode structural information. An advantage of using folding processes to generate skeletal diversity in DOS is that skeletal information can be pre-encoded into substrates in a combinatorial fashion, similar to the way protein structural information is pre-encoded combinatorially in polypeptide sequences, thus making it possible to generate skeletal diversity in an efficient manner. This efficiency was realized in the context of a fully encoded, split-pool synthesis of ∼1260 compounds potentially representing all possible combinations of building block, stereochem., and skeletal diversity elements. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Formula: C8H15NO2

The Article related to oxazolidinone combinatorial library stereoselective preparation solid phase synthesis, split pool synthesis skeletal diversity combinatorial chem oxazolidinone preparation, combinatorial matrix mol skeleton furan derivatization and other aspects.Formula: C8H15NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On February 9, 2017, Levell, Julian R.; Caferro, Thomas; Chenail, Gregg; Dix, Ina; Dooley, Julia; Firestone, Brant; Fortin, Pascal D.; Giraldes, John; Gould, Ty; Growney, Joseph D.; Jones, Michael D.; Kulathila, Raviraj; Lin, Fallon; Liu, Gang; Mueller, Arne; van der Plas, Simon; Slocum, Kelly; Smith, Troy; Terranova, Remi; Toure, B. Barry; Tyagi, Viraj; Wagner, Trixie; Xie, Xiaoling; Xu, Ming; Yang, Fan S.; Zhou, Liping X.; Pagliarini, Raymond; Cho, Young Shin published an article.Computed Properties of 168297-86-7 The title of the article was Optimization of 3-Pyrimidin-4-yl-oxazolidin-2-ones as Allosteric and Mutant Specific Inhibitors of IDH1. And the article contained the following:

High throughput screening and subsequent hit validation identified 4-isopropyl-3-(2-((1-phenylethyl)amino)pyrimidin-4-yl)oxazolidin-2-one as a potent inhibitor of IDH1R132H. Synthesis of the four sep. stereomers identified the (S,S)-diastereomer (IDH125, 1f) as the most potent isomer. This also showed reasonable cellular activity and excellent selectivity vs. IDH1wt. Initial SAR exploration identified the key tolerances and potential for optimization. X-ray crystallog. identified a functionally relevant allosteric binding site amenable to inhibitors which can penetrate the blood-brain barrier, and aided rational optimization. Potency improvement and modulation of the physico-chem. properties identified (S,S)-oxazolidinone IDH889 (5x) with good exposure and 2-HG inhibitory activity in a mutant IDH1 xenograft mouse model. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Computed Properties of 168297-86-7

The Article related to pyrimidinyloxazolidinone preparation allosteric inhibitor isocitrate dehydrogenase idh1, 2-hg, 3-pyrimidin-4-yloxazolidin-2-one, mutant idh1 inhibitor, allosteric inhibition, chirality-defined potency, preclinical in vivo activity and other aspects.Computed Properties of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On March 28, 2013, Guo, Bin; Fan, Houxing; Xin, Qisheng; Chu, Wenjing; Wang, Hui; Huang, Yanqin; Chen, Xiaoyan; Yang, Yushe published an article.Application In Synthesis of (R)-5-(Hydroxymethyl)oxazolidin-2-one The title of the article was Solubility-Driven Optimization of (Pyridin-3-yl) Benzoxazinyl-oxazolidinones Leading to a Promising Antibacterial Agent. And the article contained the following:

The solubility-driven structural modification of substituted (pyridin-3-yl)-containing hydrobenzo[b]oxazolo[3,4-d][1,4]oxazinones is described, which resulted in the development of a new series of benzo[b]oxazolo[3,4-d][1,4]oxazinone analogs with high antibacterial activity against Gram-pos. pathogens, including that against linezolid-resistant strains, and low hERG inhibition. With regard to structure-activity relationship (SAR) trends among the various substituents on the pyridyl ring, relatively small and nonbasic substituents were preferable to sterically demanding or basic substituents. Oxazolidinone ring substitution on the pyridyl ring generated analogs with antibacterial activity superior to imidazolidinone ring. Solubility was enhanced by the incorporation of polar groups, especially when compounds were converted to their prodrugs. Among the prodrugs, compound I exhibited excellent solubility and a good pharmacokinetic profile. In a MRSA systemic infection model, compound I displayed an ED50 = 5.00 mg/kg, a potency that is 2-fold better than that of linezolid. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Application In Synthesis of (R)-5-(Hydroxymethyl)oxazolidin-2-one

The Article related to oxazolooxazinone pyridyl substituted preparation solubility driven optimization antibacterial activity, antibacterial activity sar gram pos bacteria oxazolooxazinone herg inhibition, sodium phosphate prodrug solubility pharmacokinetic and other aspects.Application In Synthesis of (R)-5-(Hydroxymethyl)oxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On May 24, 2004, Pallavicini, Marco; Bolchi, Cristiano; Di Pumpo, Raffaella; Fumagalli, Laura; Moroni, Barbara; Valoti, Ermanno; Demartin, Francesco published an article.Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one The title of the article was Resolution of 5-hydroxymethyl-2-oxazolidinone by preferential crystallization and investigations on the nature of the racemates of some 2-oxazolidinone derivatives. And the article contained the following:

After ascertaining its conglomerate nature by DSC and solid-state IR analyses, 5-hydroxymethyl-2-oxazolidinone (I), whose enantiomers are very important synthons, was efficiently resolved without chiral auxiliaries by preferential crystallization from a supersaturated isopropanolic solution of (±)-I, slightly enriched in one enantiomer (3.7% ee). Favorable conditions to the entrainment were defined utilizing a previously constructed ternary phase diagram of (R)-I, (S)-I, and 2-propanol. Furthermore, the investigations were extended to other chiral 2-oxazolidinones with a functionalized Me at the 5- or 4-position finding that 5-[(tosyloxy)methyl]-2-oxazolidinone is a racemic compound, whereas just the corresponding mesylate is a conglomerate as the parent alc. I. Interestingly, 4-(hydroxymethyl)-2-oxazolidinone proved to be a racemic compound in contrast with its positional isomer I demonstrating how a relatively fine variation in the mol. structure can unpredictably influence the crystalline nature of the racemate. The X-ray structure determination carried out on (S)-(+)-I, (±)-4-(hydroxymethyl)-2-oxazolidinone and (R)-(+)-4-(hydroxymethyl)-2-oxazolidinone enlightened the importance of the hydrogen bond in determining different supramol. assembling in the two homochiral compounds with respect to the racemic one and allowed a correlation with the stability of the crystal to be made. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one

The Article related to hydroxymethyl oxazolidinone resolution preferential crystallization, phase diagram hydroxymethyl oxazolidinone resolution preferential crystallization, differential scanning calorimetry hydroxymethyl oxazolidinone resolution preferential crystallization and other aspects.Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On December 13, 2019, Warner, Christopher J. A.; Berry, Sian S.; Jones, Simon published an article.Synthetic Route of 168297-86-7 The title of the article was Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines. And the article contained the following:

A series of hydroxy-functionalized bifunctional phosphine oxides and diphosphine dioxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asym. hydrosilylation of ketimines. Bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide (R,R)-Ph(2-MeOC6H4)P(CH2)6PPh(2-MeOC6H4) (32) displayed the highest enantioselectivity of 60%. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Synthetic Route of 168297-86-7

The Article related to phosphine oxide hydroxy chiral preparation organocatalyst asym hydrosilylation ketimine, chiral aromatic amine preparation asym hydrosilylation organocatalyst phosphine oxide, diphosphine oxide phosphorus chiral preparation organocatalyst asym hydrosilylation ketimine and other aspects.Synthetic Route of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On December 16, 2011, Adams, Harry; Collins, Rebecca C.; Jones, Simon; Warner, Christopher J. A. published an article.Electric Literature of 168297-86-7 The title of the article was Enantioselective preparation of P-chiral phosphine oxides. And the article contained the following:

A highly efficient chiral auxiliary-based strategy for the asym. synthesis of P-chiral phosphine oxides in >98:2 er has been developed. Racemic phosphinyl chlorides undergo highly stereoselective asym. substitution with N-deprotonated chiral oxazolidinones, yielding chiral phosphinic amides, which react with Grignard reagents, giving chiral phosphine oxides. The methodol. involves the highly stereoselective formation of P-chiral oxazolidinones that then undergo displacement with a variety of Grignard reagents to prepare the desired phosphine oxides. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Electric Literature of 168297-86-7

The Article related to phosphine oxide chiral preparation oxazolidinone asym phosphinylation grignard reaction, substitution asym phosphinylation chiral auxiliary oxazolidinone phosphinic amide preparation, arylation alkylation phosphinic amide stereoselective preparation chiral phosphine oxide and other aspects.Electric Literature of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem