35016-63-8

Usage

Chemical Properties

Yellowish Oil

InChI:InChI=1/C9H9BrO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)/t8-/m0/s1

Upstream product

• 63-91-2 L-phenylalanine 
• 16503-53-0 2-bromo-3-phenylpropanoic acid 
• 673-06-3 D-(R)-phenylalanine 
• 507-09-5 tiolacetic acid 
• 828-02-4 (D)-phenyl-alanine 
• 60-29-7 diethyl ether 
• 76-05-1 trifluoroacetic acid 
• 673-06-3 D-β-Phenyl-α-alanine 
• 203124-97-4 (S)-2-methanesulfonyloxy-3-phenylpropionic acid 
• 497865-81-3 (R)-2-bromo-3-phenylpropionic acid D-phenylalaninamide salt 
• 5241-58-7 D-Phenylalaninamide 
• 497865-79-9 (R)-2-bromo-3-phenylpropionic acid L-phenylalanine ethyl ester salt 
• 497865-77-7 (R)-2-bromo-3-phenylpropionic acid L-phenylalanine methyl ester salt 

Downstream Products

• 1202-30-8 D-α-Hydrazino-β-phenyl-propionsaeure 
• 57359-76-9 (2R)-2-(acetylthio)-3-phenylpropanoic acid 
• 103499-63-4 (R)-2-(benzoylthio)-3-phenyl-propanoic acid 
• 740059-56-7 (R)-2-((R)-1-Carboxy-2-phenyl-ethylsulfanyl)-3-phenyl-propionic acid 
• 785748-27-8 (R)-2-((S)-1-Carboxy-2-phenyl-ethylsulfanyl)-3-phenyl-propionic acid 
• 73087-01-1 L-methyl 2-N-benzyloxycarbonyl-aminoxy-3-phenyl propanoate 
• 56985-04-7 C₁₇H₁₇NO₅ 
• 627064-69-1 (2R)-benzylthiomorpholin-3-one 
• 142695-09-8 MDL 101,628 
• 142589-10-4 (4S,7S,12bR)-7-((R)-2-Acetylsulfanyl-3-phenyl-propionylamino)-6-oxo-1,2,3,4,6,7,8,12b-octahydro-benzo[c]pyrido[1,2-a]azepine-4-carboxylic acid 
• 142589-09-1 (4S,7S,12bR)-7-((R)-2-Acetylsulfanyl-3-phenyl-propionylamino)-6-oxo-1,2,3,4,6,7,8,12b-octahydro-benzo[c]pyrido[1,2-a]azepine-4-carboxylic acid benzhydryl ester 
• 76999-53-6 Boc-D-SerψD-Phe (ψ=CH2S) 
• 604809-02-1 (R)-2-bromo-3-phenylpropionic acid cyclohexylamine salt 
• 1190832-56-4 C₁₅H₁₅BrN₂O 

Relevant academic research and scientific papers

Efficient synthesis of 5-(hydroxymethyl)piperazin-2-ones using automatically prepared chiral bromocarboxylic acid and Garner's aldehyde as versatile building blocks

An efficient method for the synthesis of substituted 5-(hydroxymethyl)piperazin-2-ones was established by using an automated synthesis process. Thirteen piperazinones were synthesized from chiral α-bromocarboxylic acids and Garner's aldehyde which were prepared by using our originally developed automated synthesizer, ChemKonzert. The automated method of synthesizing chiral α-bromocarboxylic acids was efficient and safe because the rate of the dropwise addition of the reagent can be controlled using the automated synthesizer. This method is expected to contribute to the synthesis of pharmaceuticals.

Direct synthesis of α-thio aromatic acids from aromatic amino acids

Modified amino acids are useful synthetic components in both chemistry and biology. Here we describe a simple, scalable two-step procedure to generate α-thio aromatic acids from aromatic amino acids with yields of up to 96%. Diazotization and α-lactone me

Benzoxazinone-containing 3,5-dimethylisoxazole derivatives as BET bromodomain inhibitors for treatment of castration-resistant prostate cancer

The bromodomain and extra-terminal proteins (BET) have emerged as promising therapeutic targets for the treatment of castration-resistant prostate cancer (CRPC). We report the design, synthesis and evaluation of a new series of benzoxazinone-containing 3,5-dimethylisoxazole derivatives as selective BET inhibitors. One of the new compounds, (R)-12 (Y02234), binds to BRD4(1) with a Kd value of 110 nM and blocks bromodomain and acetyl lysine interactions with an IC50 value of 100 nM. It also exhibits selectivity for BET over non-BET bromodomain proteins and demonstrates reasonable anti-proliferation and colony formation inhibition effect in prostate cancer cell lines such as 22Rv1 and C4-2B. The BRD4 inhibitor (R)-12 also significantly suppresses the expression of ERG, Myc and AR target gene PSA at the mRNA level in prostate cancer cells. Treatment with (R)-12 significantly suppresses the tumor growth of prostate cancer (TGI = 70%) in a 22Rv1-derived xenograft model. These data suggest that compound (R)-12 is a promising lead compound for the development of a new class of therapeutics for the treatment of CRPC.

Di(1-naphthyl) methanol ester of carboxylic acids for absolute stereochemical determination

The absolute stereochemistry of chiral carboxylic acids is determined as a di(1-naphthyl)methanol ester derivative. Computational scoring of conformations favoring either P or M helicity of the naphthyl groups, capable of exciton-coupled circular dichroic coupling, leads to a predicted stereochemistry for the derivatized carboxylic acids.

Substituted α-mercaptoketones, new types of specific neprilysin inhibitors

New neprilysin inhibitors containing an α-mercaptoketone HSC(R1R2)CO group, as zinc ligand were designed. Two parameters were explored for potency optimization: the size of the inhibitor which could interact with the S1, S

MIXED INHIBITORS OF AMINOPEPTIDASE N AND NEPRILYSIN

Mixed inhibitors of aminopeptidase N and neprilysin are disclosed. Pharmaceutical compositions containing at least one of these compounds, used alone or in combination with morphine and derivatives thereof, endocannabinoids and inhibitors of endocannabinoid metabolism, GABA derivatives such as gabapentin or pregabalin, duloxetine or methadone, can be used as an analgesic, anxiolytic, antidepressant or anti-inflammatory.

Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Bronsted acid catalysis

Highly enantioselective protonation of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals is achieved by using P-spiro chiral diaminodioxaphosphonium barfate as a Bronsted acid catalyst, where the enantiofacial discrimination by the catalyst mainly stems from the recognition of the electronic difference between two substituents on the ketene disilyl acetal.

Synthesis of enantiomerically enriched-bromonitriles from amino acids

Two methods were investigated for the preparation of six chiral-bromonitriles with different optic purities. The nitrous deamination of amino acids gives-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding-bromoamids using thionyl chloride gives-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.

Syntheses of hydrazino peptides and conjugates

(α-Benzyloxycarbonyl-aminoacyl)benzotriazolides (Cbz = benzyloxycarbonyl) underwent a coupling reaction with α-hydrazino acids under microwave irradiation to form hybrid hydrazino dipeptides (42-71 %). Chiral acylations of β-N-Cbz-α-hydrazino acylbenzotriazolides were successfully carried out with N-, S-, O-, and C-nucleophiles in yields of 49-88 %. Benzyloxycarbonyl-protected hybrid hydrazino dipeptides and benzyloxycarbonyl-protected hydrazino aminoacyl conjugates with N-, S-, O-, and C-nucleophiles were prepared by using benzotriazole methodology. Copyright

Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides

A reaction between imines and anhydrides has been developed with chiral disubstituted anhydrides and chiral imines. The synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and with high diastereoselectivity in most cases. Enantiomerically pure alkyl-substituted anhydrides proceed with no epimerization, thus providing access to enantiomerically pure penta-substituted lactam products.