Heterocyclic Building Blocks-Oxazolidine

Highly Enantioselective and Diastereoselective 1,3-Dipolar Cycloaddition Reactions between Azomethine Imines and 3-Acryloyl-2-oxazolidinone Catalyzed by Binaphthyldiimine-Ni(II) Complexes was written by Suga, Hiroyuki;Funyu, Akira;Kakehi, Akikazu. And the article was included in Organic Letters in 2007.Related Products of 2043-21-2 This article mentions the following:

The first examples of high levels of asym. induction (97-74% ee) along with high diastereoselectivities (>99:1-64:36) in dipole-HOMO-/dipolarophile-LUMO-controlled asym. 1,3-dipolar cycloaddn between azomethine imines and 3-acryloyl-2-oxazolidinone were reported. Fused pyrazole derivatives I were synthesized by using a chiral BINIM-Ni(II) complex as a chiral Lewis acid catalyst. In the experiment, the researchers used many compounds, for example, 3-Acryloyloxazolidin-2-one (cas: 2043-21-2Related Products of 2043-21-2).

3-Acryloyloxazolidin-2-one (cas: 2043-21-2) belongs to oxazolidine derivatives. Oxazolidines are well known as key portions of bioactive molecules or precursors of chiral molecules, as well as established chiral auxiliaries. Some reports highlighted again the effectiveness of oxazolidine-based compounds in driving the stereo- or diastereotopic outcome of chemical reactions.Related Products of 2043-21-2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

N-acyl-5,5-dimethyl-oxazolidin-2-ones as latent aldehyde equivalents was written by Bach, Jordi;Bull, Steven D.;Davies, Stephen G.;Nicholson, Rebecca L.;Sanganee, Hitesh J.;Smith, Andrew D.. And the article was included in Tetrahedron Letters in 1999.Formula: C5H9NO2 This article mentions the following:

N-acyl-5,5-dimethyl-oxazolidin-2-ones can function as versatile latent aldehyde equivalent Reductive cleavage with DIBAL-H affords aldehydes in good yield, while tandem DIBAL-H/Wittig methodol. affords α,β-unsaturated esters. In the experiment, the researchers used many compounds, for example, 5,5-Dimethyloxazolidin-2-one (cas: 1121-83-1Formula: C5H9NO2).

5,5-Dimethyloxazolidin-2-one (cas: 1121-83-1) belongs to oxazolidine derivatives. Oxazolidine-based compounds have started to attract attention also in the medicinal and materials chemistry fields. Some reports highlighted again the effectiveness of oxazolidine-based compounds in driving the stereo- or diastereotopic outcome of chemical reactions.Formula: C5H9NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

First synthesis and characterization of key stereoisomers related to Ezetimibe was written by Ren, Yun;Duan, Yan-Jun;Li, Ren-Jun;Deng, Yong;Hai, Li;Wu, Yong. And the article was included in Chinese Chemical Letters in 2014.Formula: C9H9NO2 This article mentions the following:

During a laboratory optimization and a late phase manufacturing study of the cholesterol absorption inhibitor ezetimibe, the formation of several stereoisomers was observed To study the complete stereoisomer profile of ezetimibe, the authors have synthesized and completely characterized several key stereoisomers of ezetimibe for the first time. This study will provide an access to the reference standard of these stereoisomers and may have some implications in the development of new medicines. The tilte compounds thus formed included (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone (ezetimibe) and diastereomers, such as (3R,4R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone. The synthesis of the target compounds was achieved using 2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-butanoic acid and (4S)-4-phenyl-2-oxazolidinone and (4R)-4-phenyl-2-oxazolidinone (chiral auxiliary) as starting materials. Intermediates thus formed included (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-2-azetidinone and related diastereomers. In the experiment, the researchers used many compounds, for example, (S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7Formula: C9H9NO2).

(S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7) belongs to oxazolidine derivatives. Oxazolidine-based compounds are well-known chiral auxiliaries and strategic molecular moieties in chemistry since they can effectively mask or mimic amino acid units or amino alcohols. In another report, the incorporation of an additional substituted oxazolidine ring over a range of new biphenylazepinium salt organocatalysts for the asymmetric epoxidation of alkenes improved enantiocontrol over the parent structures.Formula: C9H9NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Addition Polymerization of Norbornene-Type Monomers Using Neutral Nickel Complexes Containing Fluorinated Aryl Ligands was written by Barnes, Dennis A.;Benedikt, George M.;Goodall, Brian L.;Huang, Shyhchang S.;Kalamarides, Heather A.;Lenhard, Susan;McIntosh, Lester H. III;Selvy, K. T.;Shick, Robert A.;Rhodes, Larry F.. And the article was included in Macromolecules in 2003.Recommanded Product: Bis(2,2′,6,6′-tetramethylheptanedionato) palladium(II) This article mentions the following:

The strong Lewis acid B(C₆F₅)₃ was found to activate complexes of nickel toward the polymerization of norbornene-type monomers. The active species in this reaction is created by the transfer of C₆F₅ from boron to nickel. As a result, a class of neutral, single-component nickel complexes was developed containing two electron-withdrawing aryl ligands that polymerize norbornene and norbornenes with functional pendant groups. Active complexes include Ni(C₆F₅)₂(PPh₂CH₂C(O)Ph), (η⁶-toluene)Ni(C₆F₅)₂, and Ni(2,4,6-tris(trifluoromethyl)phenyl)₂(1,2-dimethoxyethane). In the case of (η⁶-toluene)Ni(C₆F₅)₂, isolation and characterization of low mol. weight norbornene polymers, using ethylene, indicated that each polymer chain contained a C₆F₅ headgroup. This points to the initiation step as being the insertion of norbornene into the Ni-C₆F₅ bond. The polymer microstructure as revealed by ¹H and ¹³C NMR spectrometry is entirely different from that produced using the cationic nickel catalyst, [(η³-crotyl)Ni(1,4-COD)]PF₆. This difference in microstructure led to improved mech. properties for 80:20 copolymers of norbornene and 5-triethoxysilylnorbornene. In the experiment, the researchers used many compounds, for example, Bis(2,2′,6,6′-tetramethylheptanedionato) palladium(II) (cas: 15214-66-1Recommanded Product: Bis(2,2′,6,6′-tetramethylheptanedionato) palladium(II)).

Bis(2,2′,6,6′-tetramethylheptanedionato) palladium(II) (cas: 15214-66-1) belongs to oxazolidine derivatives. Oxazolidines that are the precursor to bisoxazolidines are in effect mono-oxazolidines. They are also used as moisture scavengers in polyurethane and other systems. Chiral oxazolidines are widely used as chiral auxiliaries, chiral ligands, protecting and/or directing groups in a variety of asymmetric transformations, thanks also to their easy cleavage or their further elaboration possibilities.Recommanded Product: Bis(2,2′,6,6′-tetramethylheptanedionato) palladium(II)

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Acidic pH-Triggered Drug-Eluting Nanocomposites for Magnetic Resonance Imaging-Monitored Intra-arterial Drug Delivery to Hepatocellular Carcinoma was written by Park, Wooram;Chen, Jeane;Cho, Soojeong;Park, Sin-jung;Larson, Andrew C.;Na, Kun;Kim, Dong-Hyun. And the article was included in ACS Applied Materials & Interfaces in 2016.Product Details of 13590-42-6 This article mentions the following:

Transcatheter hepatic intra-arterial (IA) injection has been considered as an effective targeted delivery technique for hepatocellular carcinoma (HCC). Recently, drug-eluting beads (DEB) were developed for transcatheter IA delivery to HCC. However, the conventional DEB has offered relatively modest survival benefits. It can be difficult to control drug loading/release from DEB and to monitor selective delivery to the targeted tumors. Embolized DEBs in hepatic arteries frequently induce hypoxic and low pH conditions, promoting cancer cell growth. In this study, an acidic pH-triggered drug-eluting nanocomposite (pH-DEN) including superparamagnetic iron oxide nanocubes and pH-responsive synthetic peptides with lipid tails [octadecylamine-p(API-L-Asp)₁₀] was developed for magnetic resonance imaging (MRI)-monitored transcatheter delivery of sorafenib (the only FDA-approved systemic therapy for liver cancer) to HCC. The synthesized sorafenib-loaded pH-DENs exhibited distinct pH-triggered drug release behavior at acidic pH levels and highly sensitive MR contrast effects. In an orthotopic HCC rat model, successful hepatic IA delivery and distribution of sorafenib-loaded pH-DEN was confirmed with MRI. IA-delivered sorafenib-loaded pH-DENs elicited significant tumor growth inhibition in a rodent HCC model. These results indicate that the sorafenib-pH-DENs platform has the potential to be used as an advanced tool for liver-directed IA treatment of unresectable HCC. In the experiment, the researchers used many compounds, for example, (S)-Benzyl 2-(2,5-dioxooxazolidin-4-yl)acetate (cas: 13590-42-6Product Details of 13590-42-6).

(S)-Benzyl 2-(2,5-dioxooxazolidin-4-yl)acetate (cas: 13590-42-6) belongs to oxazolidine derivatives. Oxazolidine-based compounds are well-known chiral auxiliaries and strategic molecular moieties in chemistry since they can effectively mask or mimic amino acid units or amino alcohols. Oxazolidines are commonly used as metal ligands in asymmetric catalysis, synthetic intermediates in organic synthesis, and also used as the protecting groups.Product Details of 13590-42-6

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Novel approach to stereoselective synthesis of (E)/(Z)-(N-acyl-oxazolidinone)-eneglycinates was written by Zhang, Yanyan;Sun, Haopeng;You, Qidong. And the article was included in Research on Chemical Intermediates in 2015.Computed Properties of C9H9NO2 This article mentions the following:

(E)-(N-Acyl-oxazolidinone)-eneglycinates were synthesized with high stereoselectivity and in good yield by condensation of aldehydes with glycinates. (Z)-Eneglycinates could be prepared in high purity and moderate yield by transformation of (E)-eneglycinates under mild conditions. The effect on the (E)/(Z)-configuration of eneglycinates of steric hindrance by α-substituents on the aldehyde was also examined The software MMFF94 was used to explain the transformation of the thermodn. product into the kinetic product and a plausible mechanism is given. In the experiment, the researchers used many compounds, for example, (S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7Computed Properties of C9H9NO2).

(S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7) belongs to oxazolidine derivatives. Oxazolidine-based compounds have started to attract attention also in the medicinal and materials chemistry fields. Chiral oxazolidines are widely used as chiral auxiliaries, chiral ligands, protecting and/or directing groups in a variety of asymmetric transformations, thanks also to their easy cleavage or their further elaboration possibilities.Computed Properties of C9H9NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Analysis of the non-volatile components and volatile compounds of hydrolysates derived from unmatured cheese curd hydrolysis by different enzymes was written by Gao, Peng;Zhang, Wenyuan;Wei, Miaohong;Chen, Baorong;Zhu, Huiquan;Xie, Ning;Pang, Xiaoyang;Marie-Laure, Fauconnier;Zhang, Shuwen;Lv, Jiaping. And the article was included in LWT–Food Science and Technology in 2022.Application In Synthesis of 2,4,5-Trimethyloxazole This article mentions the following:

Fifteen cheese protein hydrolyzates were produced by using four different proteases. Then, the free amino acids (FAAs), mol. weight distribution (MWD), electronic tongue evaluation, and volatile compounds of the corresponding products were evaluated, resp. The results suggested that 2SD had the strongest hydrolysis characteristic, followed by 6SD and FN. Samples hydrolyzed for less than 6 h or more than 18 h contained great defects of taste. Peptides with 150 Da-450 Da were mainly responsible for bitterness, saltiness, umami, and aftertaste in some enzyme hydrolysis. Under the same total enzyme concentration condition, the sample hydrolyzed by Flavorzyme and Neutrase for 18 h released more richness and less bitterness than the other systems, which were characterized by butter and cream odor. Notably, it was found for the first time that tetramethylpyrazine (TMP) was detected in cheese proteolysis with the highest content of 17.59μg/g in Protease 2SD for 30 h. 2-Undecanone and acetoin played a key role in the flavor formation of the tested samples. Regarding the different chem. families of volatiles, acids were more abundant in the samples hydrolyzed by Protease 2SD and 6SD, while FN systems can achieve high ketone content. In the experiment, the researchers used many compounds, for example, 2,4,5-Trimethyloxazole (cas: 20662-84-4Application In Synthesis of 2,4,5-Trimethyloxazole).

2,4,5-Trimethyloxazole (cas: 20662-84-4) belongs to oxazolidine derivatives. Oxazolidine-based compounds have started to attract attention also in the medicinal and materials chemistry fields. As well as other multifunctional heterocyclic compounds, oxazolidine rings play an essential role in organic and medicinal chemistry, behaving, in some cases as powerful antitumor agents.Application In Synthesis of 2,4,5-Trimethyloxazole

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Optimization of 3-Pyrimidin-4-yl-oxazolidin-2-ones as Allosteric and Mutant Specific Inhibitors of IDH1 was written by 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. And the article was included in ACS Medicinal Chemistry Letters in 2017.Formula: C9H9NO2 This article mentions 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 IDH1^R132H. 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. IDH1^wt. 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. In the experiment, the researchers used many compounds, for example, (S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7Formula: C9H9NO2).

(S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7) belongs to oxazolidine derivatives.Oxazolidines are readily available also from propargyl amines. In another report, the incorporation of an additional substituted oxazolidine ring over a range of new biphenylazepinium salt organocatalysts for the asymmetric epoxidation of alkenes improved enantiocontrol over the parent structures.Formula: C9H9NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Iodine-catalyzed direct allylation of chiral oxazolidinones by the amide-aldehyde-alkene condensation was written by Wang, Tong-Lin;Qi, Hai-Tang;Wang, Xi-Cun;Quan, Zheng-Jun. And the article was included in Tetrahedron Letters in 2019.Formula: C9H9NO2 This article mentions the following:

An iodine-catalyzed direct allylation of chiral oxazolidinones with aldehydes and alkenes has been developed. The reaction, without use of any bases or metals, directly converted the 3-chiral oxazolidinones into N-allylated oxazolidinones. Addnl., the 3-chiral allylamine skeleton was constructed and the diastereomers were isolated by simple column chromatog. In the experiment, the researchers used many compounds, for example, (S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7Formula: C9H9NO2).

(S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7) belongs to oxazolidine derivatives. Oxazolidine-based compounds have started to attract attention also in the medicinal and materials chemistry fields. Oxazolidines are well known as key portions of bioactive molecules or precursors of chiral molecules, as well as established chiral auxiliaries.Formula: C9H9NO2

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Preparation and characterization of metaxalone nanoparticles prepared by high pressure homogenization was written by Gubbala, Lakshmi Prasanna;Arutla, Srinivas;Venkateshwarlu, Vobalaboina. And the article was included in American Journal of PharmTech Research in 2016.Synthetic Route of C12H15NO3 This article mentions the following:

The aim of present work was to enhance the dissolution of poorly soluble drug metaxalone by particle size reduction Metaxalone nanoparticles are obtained by high pressure homogenization followed by drying, which are characterized for mean particle size (MPS), polydispersityindex( PDI), zeta-potential(ZP), X-ray diffraction(XRD), Differential scanning calorimetry(DSC), Fourier-transform infra-red(FTIR), SEM (SEM), flow properties, saturation solubility and in-vitro release. The MPS of nanoparticles was observed to be less than 200 nm. The neg. ZP indicates the stable nanoparticles obtained by sufficient adsorption of the stabilizers onto drug surface. The XRD and DSC show the retention of drug crystallinity. Out of three drying methods, SD and SG have obtained stable nanoparticles with improved flow properties. Nanoparticles increased the drug solubility by approx. 4 folds with Hydroxy Pr Me cellulose and sodium lauryl sulfate as surface stabilizers. In-vitro release studies showed a remarkable increase in rate of drug release from 3 % (pure drug) to 34-36 % (nanoparticles) after 15 min and at the end of dissolution study almost 95 % of drug dissolved when compared to only 30 % of pure drug. The combining methods of HPH followed by SD/SG was observed to be promising method to produce stable nanoparticles of metaxalone with remarkable increase dissolution rate.. Results from this study suggest that these metaxalone nanoparticles may be a potential candidate for oral administration with quick onset of action for relief of acute painful musculoskeletal conditions. In the experiment, the researchers used many compounds, for example, 5-((3,5-Dimethylphenoxy)methyl)oxazolidin-2-one (cas: 1665-48-1Synthetic Route of C12H15NO3).

5-((3,5-Dimethylphenoxy)methyl)oxazolidin-2-one (cas: 1665-48-1) belongs to oxazolidine derivatives.Oxazolidines are readily available also from propargyl amines. Oxazolidines are cyclic condensation products of β-amino alcohols and aldehydes or ketone, and they undergo a facile and complete hydrolysis in aqueous solution. Alterations in carbonyl moiety control the rate of formation of a given β-amino alcohol. Oxazolidines are weaker bases (pKa 6–7) than parent β-amino alcohols and found to be more lipophilic than the parent compound at physiological pH.Synthetic Route of C12H15NO3

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem