Category: oxazolidine

On September 12, 2009, Davies, Stephen G.; Elend, Dirk L.; Jones, Simon; Roberts, Paul M.; Savory, Edward D.; Smith, Andrew D.; Thomson, James E. published an article.Electric Literature of 168297-86-7 The title of the article was The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of α-vinyl-β-hydroxy carboxylic acid derivatives and conversion to α-ethylidene-β-hydroxy esters (β-substituted Baylis-Hillman products). And the article contained the following:

The synthesis of α-vinyl-β-hydroxy esters and α-ethylidene-β-hydroxy esters (β-substituted Baylis-Hillman products) via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-iso-Pr SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from the auxiliary gives α-vinyl-β-hydroxy esters in >98% de and >98% ee. Subsequent isomerization of the double bond into conjugation provides α-ethylidene-β-hydroxy esters (β-substituted Baylis-Hillman products) in high diastereo- and enantiopurity (≥91:9 [(E):(Z)] and >98% ee). 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 hydroxy ester vinyl ethylidene stereoselective preparation aldol crotonoyloxazolidinone, Aliphatic Compounds: Carboxylic Acids and Peroxycarboxylic Acids and Their Sulfur-Containing Analogs and Salts and other aspects.Electric Literature of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On June 6, 2019, Mohamed, Shahul Hameed Peer; Bharatham, Nagakumar; Katagihallimath, Nainesh; Sharma, Sreevalli; Nandishaiah, Radha; Ramachandran, Vasanthi published a patent.Product Details of 97859-49-9 The title of the patent was Preparation of anti-bacterial heterocyclic compounds. And the patent contained the following:

The title compounds I [R1 = alkyl, cycloalkyl, alkylamino, etc.; R2 = H, F, Cl, etc.; R3 = H, alkyl, F, etc.; X1 = N or CR4 (wherein R4 = H, halo, cyano, etc.); X2 = N or CR5 (R5 = H, halo, cyano, etc.); X3 = N or CR6; and X4 = CR6 when dotted line represents a bond (R6 = H, cyano, alkyl, etc.); or X3 = CH2 or O; and X4 = CH2 when dotted line represents no bond; n = 0-2; Y1 and Y2 = (independently) N or CR7 (R7 = H, halo, cyano, etc.); Z1 = O, S, NH, CH2; R8 = H, OH, alkyl, F] along with their stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms, and pharmaceutically active derivatives thereof, useful for killing or inhibiting the growth of a microorganism selected from the group consisting of bacteria, virus, fungi, and protozoa, were prepared E.g., a multi-step synthesis of (S)-II, starting 6-methoxy-1,5-naphthyridin-4-ol and chloro(chloromethyl)dimethylsilane, was described. Exemplified compounds I were tested for their antibacterial activity (data given). Pharmaceutical compositions comprising compound I, alone and in combination with at least one antibiotic, were disclosed. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Product Details of 97859-49-9

The Article related to heterocyclic compound pyridooxazinone pyrazinooxazinone preparation antibacterial antiviral antifungal protozoacide, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Product Details of 97859-49-9

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On January 4, 2019, Peer Mohamed, Shahul Hameed; Bharatham, Nagakumar; Katagihallimath, Nainesh; Sharma, Sreevalli; Nandishaiah, Radha; Ramachandran, Vasanthi published a patent.SDS of cas: 97859-49-9 The title of the patent was Preparation of anti-bacterial heterocyclic compounds. And the patent contained the following:

The title compounds I [R1 = alkyl, cycloalkyl, alkylamino, etc.; R2 = H, F, Cl, etc.; R3 = H, alkyl, F, etc.; X1 = N or CR4 (wherein R4 = H, halo, cyano, etc.); X2 = N or CR5 (R5 = H, halo, cyano, etc.); X3 = N or CR6; and X4 = CR6 when dotted line represents a bond (R6 = H, cyano, alkyl, etc.); or X3 = CH2 or O; and X4 = CH2 when dotted line represents no bond; n = 0-2; Y1 and Y2 = (independently) N or CR7 (R7 = H, halo, cyano, etc.); Z1 = O, S, NH, CH2; R8 = H, OH, alkyl, F] along with their stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms, and pharmaceutically active derivatives thereof, useful for killing or inhibiting the growth of a microorganism selected from the group consisting of bacteria, virus, fungi, and protozoa, were prepared E.g., a multi-step synthesis of (S)-II, starting 6-methoxy-1,5-naphthyridin-4-ol and chloro(chloromethyl)dimethylsilane, was described. Exemplified compounds I were tested for their antibacterial activity (data given). Pharmaceutical compositions comprising compound I, alone and in combination with at least one antibiotic, were disclosed. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).SDS of cas: 97859-49-9

The Article related to heterocyclic compound pyridooxazinone pyrazinooxazinone preparation antibacterial antiviral antifungal protozoacide, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.SDS of cas: 97859-49-9

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On July 3, 2014, Yang, Yushe; Guo, Bin; Li, Zhan; Li, Wei published a patent.Synthetic Route of 97859-49-9 The title of the patent was Benzoxazine-oxazolidinone compounds as antiinfective agents and their preparation, pharmaceutical compositions and use in the treatment of multidrug resistant bacterial infections. And the patent contained the following:

Disclosed are benzoxazine-oxazolidinone compounds of formula I and their optical isomers, pharmaceutically acceptable salts, preparation method and application in preparing drugs for treating an infectious disease and in particular, an infectious disease caused by multidrug resistant bacteria. Compounds of formula I wherein R1 is amino and derivatives, phosphonate, succinate, L-arginine; R2 is (un)branched alkyl; R3 is halo, CN, OH, amino and derivatives, etc.; and their optical isomers, pharmaceutically acceptable salts thereof, are claimed. Compounds of formula I were prepared by using cross-coupling as the key steps. All the invention compounds were evaluated for their antibacterial activity. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Synthetic Route of 97859-49-9

The Article related to benzoxazine oxazolidinone preparation antiinfective treatment multidrug resistant bacterial infection, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Synthetic Route of 97859-49-9

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On November 28, 2017, Lu, Hualong published a patent.Electric Literature of 97859-49-9 The title of the patent was Preparation of oxazolidinone compounds as antibiotic agents. And the patent contained the following:

The title compounds shown in general formula I [wherein, R1 is selected from the groups as 3-amino-pyrrolidin-1-yl, N-methyl-3-amino-piperidin-1-yl, (R)-3-aminohexahydroazepin-1-yl, N-methyl-piperazin-1-yl, 3-methyl-piperazin-1-yl, pyrrol-1-yl, 3-methylpyrrol-1-yl, etc.; R2 is selected from H, hydroxy, Me, halogen, etc.; R3 is selected form OH, NHCOCH3, etc.] or pharmaceutically acceptable salts or isomers thereof were prepared as antibiotic agents. For example, compound II was prepared in a multi-step synthesis. The inventive compound can be applied in preparing the drugs for treating microbial infection, and II showed antibacterial activities against both Staphylococcus aureus and Staphylococcus epidermidis with MIC values of 0.25 μg/mL. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Electric Literature of 97859-49-9

The Article related to preparation oxazolidinone antibiotic agent treatment human bacterial infection, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Electric Literature of 97859-49-9

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 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 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 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

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