99359-32-7

Basic information

• Product Name: METHYL 4-BROMO-L-PHENYLALANINATE HYDROCHLORIDE
• Synonyms: METHYL 4-BROMO-L-PHENYLALANINATE HYDROCHLORIDE;Methyl 4-broMo-l-phenylalaninate, HCl;(S)-Methyl 2-aMino-3-(4-broMophenyl)propanoate hydrochloride;H-Phe(4-Br)-Ome.HCl;4-Bromo-L-phenylalanine methyl ester HCl;L-4-Bromophenylalanine methyl ester hydrochloride;4-Bromo-L-phenylalanine methyl ester hydrochloride;H-Phe(4-Br)
• CAS NO: 99359-32-7
• Molecular Formula: C10H13BrClNO2
• Molecular Weight: 294.57
• Mol File: 99359-32-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: METHYL 4-BROMO-L-PHENYLALANINATE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-BROMO-L-PHENYLALANINATE HYDROCHLORIDE(99359-32-7)
• EPA Substance Registry System: METHYL 4-BROMO-L-PHENYLALANINATE HYDROCHLORIDE(99359-32-7)

Safety Data

• Hazardous Substances Data: 99359-32-7(Hazardous Substances Data)

Usage

Uses

Methyl 4-bromo-L-phenylalaninate, HCl

Upstream product

• 67-56-1 methanol 
• 62129-39-9 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine 
• 14091-15-7 p-bromo-DL-phenylalanine 
• 62561-74-4 (2R)-2-amino-3-(4-bromophenyl)propanoic acid 
• 24250-84-8 H-p-BrPhe-OH 

Downstream Products

• 1378243-33-4 C₂₂H₃₂BrN₃O₅S 
• 1616735-89-7 C₂₀H₂₅N₅O₄ 
• 1616735-97-7 C₁₄H₁₅N₅O₂*C₂HF₃O₂ 
• 132067-41-5 methyl (±)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 1431556-44-3 C₁₃H₁₆BrNO₄ 
• 24250-84-8 H-p-BrPhe-OH 
• 62561-74-4 (2R)-2-amino-3-(4-bromophenyl)propanoic acid 
• 1431556-69-2 C₁₃H₁₆BrNO₄ 

Relevant articles and documents

Development of sulfahydantoin derivatives as β-lactamase inhibitors

Sulfahydantoin-based molecules may provide a means to counteract antibiotic resistance, which is on the rise. These molecules may act as inhibitors of β-lactamase enzymes, which are key in some resistance mechanisms. In this paper, we report on the synthe

Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes

The rhodium-catalyzed asymmetric ring opening reaction of oxabicyclic alkenes is shown to be an efficient method for synthesizing chiral heterocycles. We demonstrate that the pairwise combination of chiral catalyst with chiral amino-acid-derived pronucleophiles results in a stereodivergent synthesis of diastereomeric hydroxyesters. A favorable conformational preference induces the subsequent lactonization of one diastereomer leading to the highly enantioselective synthesis of oxazinones.

Method for synthesizing AHU377 calcium salt

The invention discloses a method for synthesizing an AHU377 calcium salt. The method comprises the following steps: reacting 4-bromo-D-phenylalanine with thionyl chloride, reacting obtained methyl 4-bromo-D-phenylalaninate hydrochloride with BOC acid anhydride, reacting the obtained reaction product with phenylmagnesium bromide to obtain N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methylester, reacting the N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methyl ester with sodium borohydride, reacting the obtained reaction product with ethyl 2-(triphenylphosphoranylidene)propionate to obtain ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoate, reacting the ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoatewith lithium hydroxide, performing catalytic hydrogenation, reacting the obtained catalytic hydrogenation product with thionyl chloride to obtain ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, and stirring and reacting the ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, calcium chloride and succinic anhydride to obtain the target product.The method has the advantages of simple steps, mild reaction conditions, high purity and high yield.

HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF DISEASE

Heterocyclic compounds are described that are lysophosphatidic acid receptor ligands that are useful in the treatment of lysophosphatidic acid receptor-dependent diseases and conditions, including but not limited to diseases involving fibrosis, such as fibrosis of the heart, kidney, liver and lung, and scleroderma; inflammatory diseases such as diabetic nephropathy and inflammatory bowel disease; ocular diseases such as diseases involving retinal degeneration; nerve diseases such as pruritus and pain. Non-limiting examples of those compounds include (RS)-3-Cyclopropyl-2-{4-[3-methyl-4((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-benzyloxy}-propionic acid and (R)-1-(4′-{5-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-4-fluoro-pyrazol-1-yl}-2-fluoro-biphenyl-4-yl)-cyclopropanecarboxylic acid.

TETRAZINE-CONTAINING COMPOUNDS AND SYNTHETIC METHODS THEREOF

Described herein are tetrazine derivatives and efficient synthetic methods of synthesis thereof using elimination-Heck cascade reaction. Provided herein is the synthesis of conjugated tetrazines from the tetrazine derivatives. Also provided herein are met

In situ synthesis of alkenyl tetrazines for highly fluorogenic bioorthogonal live-cell imaging probes

In spite of the wide application potential of 1,2,4,5-tetrazines, particularly in live-cell and in vivo imaging, a major limitation has been the lack of practical synthetic methods. Here we report the in situ synthesis of (E)-3-substituted 6-alkenyl-1,2,4

Enzymatic synthesis of chiral phenylalanine derivatives by a dynamic kinetic resolution of corresponding amide and nitrile substrates with a multi-enzyme system

Mutant α-amino-ε-caprolactam (ACL) racemase (L19V/L78T) from Achromobacter obae with improved substrate specificity toward phenylalaninamide was obtained by directed evolution. The mutant ACL racemase and thermostable mutant D-amino acid amidase (DaaA) from Ochrobactrum anthropi SV3 co-expressed in Escherichia coli (pACLmut/pDBFB40) were utilized for synthesis of (R)-phenylalanine and non-natural (R)-phenylalanine derivatives (4-OH, 4-F, 3-F, and 2-F-Phe) by dynamic kinetic resolution (DKR). Recombinant E. coli with DaaA and mutant ACL racemase genes catalyzed the synthesis of (R)-phenylalanine with 84% yield and 99% ee from (RS)-phenylalaninamide (400 mM) in 22 h. (R)-Tyrosine and 4-fluoro-(R)-phenylalanine were also efficiently synthesized from the corresponding amide compounds. We also co-expresed two genes encoding mutant ACL racemase and L-amino acid amidase from Brevundimonas diminuta in E. coli and performed the efficient production of various (S)-phenylalanine derivatives. Moreover, 2-aminophenylpropionitrile was converted to (R)-phenylalanine by DKR using a combination of the non-stereoselective nitrile hydratase from recombinamt E. coli and mutant ACL racemase and DaaA from E. coli encoding mutant ACL racemase and DaaA genes. Copyright

Synthesis and biological evaluation of new active For-Met-Leu-Phe-OMe analogues containing para-substituted Phe residues

In the present study, we report synthesis and biological evaluation of the N-Boc-protected tripeptides 4a-l and N-For protected tripeptides 5a-l as new For-Met-Leu-Phe-OMe (fMLF-OMe) analogues. All the new ligands are characterized by the C-terminal Phe residue variously substituted at position 4 of the aromatic ring. The agonism of 5a-l and the antagonism of 4a-l (chemotaxis, superoxide anion production, lysozyme release as well as receptor binding affinity) have been examined on human neutrophils. No synthesized compounds has higher activity than the standard fMLF-OMe tripeptide to stimulate chemotaxis, although compounds 5a and 5c with -CH3 and -C(CH3)3, respectively, in position 4 on the aromatic ring, are better than the standard tripeptide to stimulate the production of superoxide anion, in higher concentration. Compounds 4f and 4i, containing -F and -I in position 4, respectively, on the aromatic ring of phenylalanine, exhibit significant chemotactic antagonism. The influence of the different substitution at the position 4 on the aromatic ring of phenylalanine is discussed.

Phenylalanine-containing hydroxamic acids as selective inhibitors of class IIb histone deacetylases (HDACs)

We synthesized biarylalanine-containing hydroxamic acids and tested them on immunoprecipitated HDAC1 and HDAC6 and show a subtype selectivity for HDAC6 that was confirmed in cells by Western blot (tubulin vs histones). We obtained an X-ray structure with

COMPOUNDS FOR THE INHIBITION OF INTEGRINS AND USE THEREOF

The present invention is related to a compound of formula (I), wherein A is a nonaromatic heterocyclic ring, Ar is either absent or phenylene; psi is a radical of formula (II), R2 is a hydrophobic moiety; and G is a radical containing one or more moieties selected from the group consisting of NH, OH and a basic moiety. The compounds are inhibitors of integrins, especially antagonists of the fibronectin receptor alpha5beta1, useful as anti-angiogenic agents.