The Best Chemistry compound: (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one

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Methods are disclosed to treat or prevent at least one disease or condition in a subject in need thereof comprising administering a compound of Formula (I): (I) or a pharmaceutically acceptable salt, or ester thereof, wherein R1 and R2 are independently chosen from a hydrogen atom or linear, branched, and/or cyclic C1 -C6 alkyl groups, with the proviso that R1 and R2 are not both hydrogen or a pharmaceutically acceptable salt or ester thereof. Such diseases or conditions may relate to coronary heart disease (CHD), for example atherosclerosis; metabolic syndrome/insulin resistance; and/or a dyslipidemic condition such as hypertriglyceridemia (HTG), elevated LDL- cholesterol, elevated total-cholesterol, elevated Apo B and low HDL-cholesterol. The present disclosure further provides for a method of reducing atherosclerosis development. Pharmaceutical compositions comprising a compound of Formula (I) are also disclosed.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2116NO – PubChem

 

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A method of making a phenylethylamine of formula B: wherein R2, R3, R4, R5, R6, Ralpha, Rbeta and Rn are each independently selected from hydrogen, alkyl, acyl, aryl, amido, amino acids, sugars and nucleotides. The method includes the reduction of a compound of formula A in the absence of base: wherein R2, R3, R4, R5, R6, Ralpha, Rbeta and Rn are as defined above.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2124NO – PubChem

 

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A novel preparation of (+)-methyl pederate (4), a key intermediate in syntheses of mycalamides (1), marine natural products from a New Zeland sponge of the genus Mycale, is described. The key step involves palladium- catalyzed intramolecular allylic alkylation of the carbonate 21, derived from (+)-(4R,5R,E)-5-(tert-butyldimethylsiloxy)-4-methyl-2-hexenol (13), yielding lactones 5 in 87% yield. Demethoxycarbonylation of the cyclization products 5 and further functional group transformations led to (+)-methyl pederate (4).

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2193NO – PubChem

 

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In reactions of (2,3-anti)-3-amino-1,2-diols with diphosgene and phosgene and their conversion into 1,3-oxazolidin-2-ones, some differences in the stereochemistry of the reactions have been found with these two reagents. The reactions with phosgene afforded the expected cis-oxazolidinones, and in the reaction with diphosgene under the same reaction conditions, the trans-oxazolidinones were also obtained.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2161NO – PubChem

 

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Going to trial: From about 350 active epothilone analogues synthesized by a highly convergent synthesis, one (ZK-EPO, see picture) has been chosen for clinical development on the basis of its outstanding preclinical data. This compound exhibits higher activity and efficacy than taxanes (e.g. paclitaxel) and second-generation epothilones, a fast and efficient cellular uptake, no recognition by efflux mechanisms, and an improved therapeutic window. (Chemical Equation Presented)

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2178NO – PubChem

 

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An efficient approach to access functionalized tertiary-type beta-hydroxyl carboxamides has been developed through Sc(OTf)3-catalyzed addition of ynamides and substituted ketones. Water was found to be an important reaction substrate, and the solvent was not needed in this process. A broad range of substituted ynamides and ketones was well applicable to the reaction with excellent chemical selectivities. Moreover, several chiral beta-hydroxyl carboxamides 3j-3r were prepared with excellent regioselectivities and outstanding diastereoselectivities.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2180NO – PubChem

 

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Two convergent total synthe-ses of the ansa-polyketide (-)-kendo-mycin (1) are described. The syntheses benefit from the use of readily avail-able and cheap starting materials. Highly complex diastereoselective Claisen-Ireland rearrangements were used to introduce the (E)-double bond and the C16-Me group. The ring clo-sure of the strained ansa macrocycle was achieved by ring-closing metathesis and a highly efficient combination of macrolactonization and photo-Fries re-action. A protecting group free end-game via an unstable o-quinone is pre-sented. Additionally some unsuccessful synthetic efforts towards the total synthesis of 1 are described.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2181NO – PubChem

 

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An asymmetric synthesis of a selective endothelin A receptor antagonist 1b is described. Asymmetric conjugate addition of aryllithium derived from 18 to the chiral oxazoline 17 followed by hydrolysis afforded 15 in 96% ee via purification as (S)-(-)-1-phenylethylamine salt. Pd(OAc)2/dppf (1,1?-bis(diphenylphosphino)ferrocene) catalyzed carbonylation followed by chemoselective addition of aryllithium derived from 23 which gave ketone 24. Diastereoselective reduction of the ketone with catecholborane followed by concomitant activation of the resulting alcohol and cyclization gave the late intermediate 26. Introduction of amino moiety on the pyridine ring by imidoyl rearrangement followed by deprotection and purification by crystallization furnished the enantiomerically pure target molecule 1b in 8% overall yield from 16.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2173NO – PubChem

 

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A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-aza-bicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into g-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobu-tane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant is described.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2175NO – PubChem

 

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Small molecules that induce or stabilize the association of macromolecules have proven to be useful effectors of a wide variety of biological processes. To date, all examples of such chemical inducers of dimerization have involved known ligands to well-characterized proteins. The generality of this approach could be broadened by enabling the discovery of heterodimerizers that target known macromolecules having no established ligand, or heterodimerizers that produce a novel biologic response in screens having no predetermined macromolecular target. Toward this end, we report the construction of a diversified library of synthetic heterodimerizers consisting of an invariant ligand that targets the FK506-binding protein (AP1867) attached to 320 substituted tetrahydrooxazepines (THOXs). The THOX components were generated by a combination of liquid- and solid-phase procedures employing sequential Mitsonobu displacements to join two structurally diversified olefin-containing monomers, followed by ruthenium-mediated olefin metathesis to effect closure of the seven-membered ring. The 320 resin-bound THOX ligands were coupled in parallel to AP1867, and the products were released from the resin to yield candidate heterodimerizers in sufficient yield and purity to be used directly in biologic testing. A representative panel of 25 candidate heterodimerizers were tested for their ability to pass through the membrane of human fibrosarcoma cells, and all were found to possess activity in this tissue culture system. These studies pave the way for further studies aimed at using small-molecule inducers of heterodimerization to effect novel biological responses in intact cells.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2179NO – PubChem