143589-97-3

Usage

Chemical Properties

Yellow Solid

Upstream product

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 104-01-8 4-Methoxyphenylacetic acid 
• 4732-69-8 Chloro-oxo-acetic acid 
• 126702-34-9 C₁₄H₁₈O₄ 

Downstream Products

• 169176-61-8 (2S,4S)-3-<2-Azido-2-(4-methoxyphenyl)-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone 
• 917379-10-3 (S)-4-benzyl-3-((S)-3-(2-bromo-4-methoxyphenyl)-2-(4-methoxyphenyl)propanoyl)-2-oxazolidinone 
• 143589-98-4 3-[1-oxo-2(S)-(4-methoxyphenyl)propyl]-4(S)-(phenylmethyl)-2-oxazolidinone 
• 917379-11-4 (S)-3-(2-bromo-4-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-ol 
• 531-95-3 equol 
• 3722-56-3 (S)-7-methoxy-3-(4-methoxyphenyl)chromane 
• 286967-33-7 2(S)-(4-methoxyphenyl)propyl-1-bromide 
• 286967-34-8 2(S)-(4-methoxyphenyl)-1-propanol methanesulfonate 
• 286967-35-9 1-trimethylsilyloxy-3(S)-[2(S)-(4-methoxyphenyl)-1-propyl]-5(R)-methyl-1-cyclohexene 
• 93397-63-8 (S)-4-methoxy-β-methylbenzeneethanol 
• 169273-94-3 (S)-(N-benzyloxycarbonyl)-p-methoxyphenylglycine 
• 169176-62-9 (2S,4S)-3-<2-<<(Phenylmethoxy)carbonyl>amino>-2-(4-methoxyphenyl)-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone 
• 169176-57-2 N--L-(4-methoxyphenyl)glycinyl>-D-(3-hydroxy-4-methoxyphenyl)glycine ethyl ester 
• 169176-69-6 (1R,2R)-amino>-3-hydroxy-3-oxopropyl>phenoxy>-4-methoxyphenyl>-2-ethoxy-2-oxoethyl>amino>-(S)-(4-methoxyphenyl)glycine 

Relevant academic research and scientific papers

A chiral pool approach for asymmetric syntheses of both antipodes of equol and sativan

For the first time, both antipodes of the isoflavans, equol and sativan were synthesized in >98% ee with good overall yields starting from readily available starting materials. The chiral isoflavan, (?)-equol is produced from soy isoflavones, formonentin and daidzein by the action of intestinal bacteria in certain groups of population and other chiral isoflavans are reported from various phytochemical sources. To produce these chiral isoflavans in gram quantities, Evans’ enantioselective aldol condensation was used as a chiral-inducing step to introduce the required chirality at the C-3 position. Addition of chiral boron-enolate to substituted benzaldehyde resulted in functionalized syn-aldol products with >90% yield and excellent diastereoselectivity. Functional group transformations followed by intramolecular Mitsunobu reaction and deprotection steps resulted the target compounds, S-(?)-equol and S-(+)-sativan, with high degree of enantiopurity. By simply switching the chiral auxiliary to (S)-4-benzyloxazolidin-2-one and following the same synthetic sequence the antipodes, R-(+)-equol and R-(?)-sativan were achieved. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. This flexible synthetic process lends itself quite readily to the enantioselective syntheses of other biologically active C-3 chiral isoflavans.

Diarylpropionitrile (DPN) enantiomers: Synthesis and evaluation of estrogen receptor β-selective ligands

Two estrogen receptor (ER) subtypes, ERα and ERβ, mediate the actions of estrogens in diverse reproductive and nonreproductive target tissues. ER subtype-selective ligands, which bind to and activate these subtypes differentially, have proved to be useful

Inhibitors of protein kinases

Compounds of general Formula (I): wherein R1, R2, R3, Ra, A, B and x are as defined herein are inhibitors of protein kinases in particular members of the cyclin-dependent kinase family and/or the glycogen synthase kinase 3 family and are useful in preventing and/or treating any type of pain, inflammatory disorders, cancer, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases, metabolic disorders, renal diseases, neurologic and neuropsychiatric diseases and neurodegenerative diseases.

Process for selective synthesis of enantiomers of substituted 1-(2-amino-1-phenyl-ethyl)-cyclohexanols

A process for the enantioselective synthesis of an (S)— or (R)-1-[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol and analogues or salt thereof are described. The method involves the steps of (a) reacting an (S) or (R) 4-benzyloxazolidinone with a mixed anhydride of a methyoxyphenylacetic acid under conditions which form a oxazolidinone, (4S)— or (4R)-4-benzyl-3-[methyoxyphenyl]acetyl]-oxazolidin-2-one, (b) treating the (4S)— or (4R)-4-benzyl-3-[(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one with an aprotic amine base and titanium chloride in a chlorinated solvent under conditions which permit formation of the corresponding anion, (c) mixing the corresponding anion with titanium chloride and cylcohexanone under conditions which permit an aldol reaction to form the corresponding (4S)— or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one, (d) hydrolyzing the (4S)— or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one to form a chiral acid (2S or 2R)-(1-hydroxycyclohexyl)-methoxyphenyl)acetic acid, (e) coupling the chiral phenylacid to a secondary amine to form an amide, and (f) reducing the amide to form an (S) or (R) 1[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol or a salt thereof.

Synthesis and SAR of succinamide peptidomimetic inhibitors of cathepsin S

Peptidic, non-covalent inhibitors of lysosomal cysteine protease cathepsin S (1 and 2) were investigated due to low oral bioavailability, leading to an improved series of peptidomimetic inhibitors. Utilizing phenyl succinamides as the P2 residue increased the oral exposure of this lead series of compounds, while retaining selective inhibition of the cathepsin S isoform. Concurrent investigation of the P1 and P2 subsites resulted in the discovery of several potent and selective inhibitors of cathepsin S with good pharmacokinetic properties due to the elimination of saturated aliphatic P2 residues.

Total synthesis of (S)-equol

The first enantioselective total synthesis of (S)-equol is reported. The described route relies on an Evans alkylation to form the stereocenter and an intramolecular Buchwald etherification to generate the chroman ring. Key features of this method include its brevity, its scalability, and the low cost of starting materials.

HIV PROTEASE INHIBITORS

Peptide mimics, having a constrained peptide backbone conformation, are HIV protease inhibitors. A compound of this invention is, for example, 3-Benzyl-5(alaninyl-1-aminoethyl)-2,3,6,7-tetrahydro-N-azepinyl-2-propionyl-valinyl-valinyl methyl ester.

Synthesis of a 16-Membered Cyclic Peptide Model of the BCF Rings of Ristocetin A Using Arene-Ruthenium Chemistry Coupled with Cycloamidation

A convergent synthetic approach to the cyclic peptide 4, which is a model for the B/C/F ring system of ristocetin B, is described.A key reaction is the coupling of the phenolic dipeptide 5, constructed from arylglycine subunits, with the chlorophenylalanine-RuCp cationic complex 6, followed by demetalation of the product to give the diaryl ether 7, without epimerization at any of the amino acid residues.Deprotection of 7 followed by cycloamidation affords the target molecule 4, produced as a mixture of atropdiastereomers which were separated and characterized by NMR spectroscopy.