67470-21-7

Basic information

• Product Name: L-Tyrosine, 3,5-dibroMo-, Methyl ester
• Synonyms: L-Tyrosine, 3,5-dibroMo-, Methyl ester;(S)-Methyl 2-aMino-3-(3,5-dibroMo-4-hydroxyphenyl)propanoate;(S)-Methyl 2-aMino-3-(3,5-dibroMo-4-hydroxyphenyl)propanoate
• CAS NO: 67470-21-7
• Molecular Formula: C₁₀H₁₁Br₂NO₃
• Molecular Weight: 353.00724
• Mol File: 67470-21-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Tyrosine, 3,5-dibroMo-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tyrosine, 3,5-dibroMo-, Methyl ester(67470-21-7)
• EPA Substance Registry System: L-Tyrosine, 3,5-dibroMo-, Methyl ester(67470-21-7)

Safety Data

• Hazardous Substances Data: 67470-21-7(Hazardous Substances Data)

Upstream product

• 300-38-9 3,5-dibromo-L-tyrosine 
• 67-56-1 methanol 
• 60-18-4 L-tyrosine 
• 355857-30-6 (+)-(S)-methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-(2-methylprop-2-yloxycarbamoyl)propanoate 
• 3417-91-2 L-tyrosine methyl ester HCl 

Downstream Products

• 105189-44-4 3,5-dibromo-N-trifluoroacetyl-L-tyrosine methyl ester 
• 160538-38-5 methyl (S)-2-(((benzyloxy)carbonyl)amino)-3-(3,5-dibromo-4-hydroxyphenyl)propanoate 
• 372963-96-7 (S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester 
• 372964-03-9 (S)-2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester 
• 372963-97-8 (S)-2-{(2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3-methyl-pentanoylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester 
• 246512-36-7 (S)-2-[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester 
• 246512-37-8 (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester 
• 83118-65-4 Isodityrosine 
• 113311-35-6 H-Isodityr-OMe 
• 160538-39-6 (S)-2-Benzyloxycarbonylamino-3-{4-[5-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3-bromo-2-hydroxy-phenoxy]-3,5-dibromo-phenyl}-propionic acid methyl ester 
• 115663-82-6 (S)-3-[3,5-Dibromo-4-(1,3,5-tri-tert-butyl-4-oxo-cyclohexa-2,5-dienyloxy)-phenyl]-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester 
• 123418-36-0 (9S,12S,15S)-9-Acetylamino-4-hydroxy-12-(4-hydroxy-benzyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid 
• 123418-35-9 (9S,12S,15S)-9-Acetylamino-4-hydroxy-12-(4-hydroxy-benzyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester 
• 123418-34-8 (9S,12S,15S)-9-tert-Butoxycarbonylamino-4-hydroxy-12-(4-hydroxy-benzyl)-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester 

Relevant articles and documents

A novel class of tyrosine derivatives as dual 5-LOX and COX-2/mPGES1 inhibitors with PGE2 mediated anticancer properties

Leukotriene and prostaglandin pathways are controlled by the enzymes, LOX and COX/mPGES1 respectively and are responsible for inflammatory responses. PGE2, produced by mPGES1, leads to the progression of inflammation as well as cancer. A series of 19 novel tyrosine derivatives are synthesized, characterized and tested against 5-LOX, in vitro, and production of PGE2, in HeLa cells. 6b-v and 6c-i, are found to possess maximum inhibitory action against 5-LOX and PGE2 production. The compound 6b-v is found to act by disrupting the redox cycle of the 5-LOX enzyme, and its activity is comparable to that of the commercial drug, Zileuton. The activity of the other compound 6c-i is comparable to a drug in clinical trials, Licofelone, and it has been found to inhibit the mRNA expression of mPGES1 predominantly. It also arrests the HeLa cells in the S and G2/M phases of the cell cycle indicating anticancer activity. Also, compounds, 6b-iv and 6b-viii inhibit both the LT & PG pathways in the inflammation cascade. Presence of iodine in the phenyl ring appears to favour the inhibition of 5-LOX whereas chlorine favours the inhibition of PGE2 production. These leads could be further optimized and developed as drugs against inflammation and cancer.

Anti-parasite and cytotoxic activities of chloro and bromo L-tyrosine derivatives

A series of twenty-one L-tyrosine derivatives with modifications in the halogenation pattern of the aromatic ring and different degree of methylations on the amine and phenolic hydroxyl groups were synthesized. The structures of all the intermediates and target compounds were confirmed unambiguous by spectroscopy analysis. Additionally, all compounds were evaluated against Plasmodium falciparum and Leishmania panamensis parasites between 20-702 μg mL-1. The cytotoxic evaluation was done to determine the selectivity index for each compound. Six compounds had the lower EC50 (effective concentration 50) against L. panamensis. One of these compounds was the most active with an EC50 at 24.13 μg mL-1 (76.07 μM). All derivatives showed no significant activity against P. falciparum and no compound has in vitro antifungal activity at 500 μg mL-1.

Synthesis of Isodityrosine, Dityrosine and Related Compounds by Phenolic Oxidation of Tyrosine and Phenylglycine Derivatives Using an Electrochemical Method

The phenolic oxidation of L-tyrosine derivatives by electrolysis and zinc reduction produced the coupling products leading to isodityrosine and dityrosine.The oxidation mode could be controlled by altering halogen substituents (Br or I) at two ortho positions of phenol groups.Additionally, this methodology was applied to 4-hydroxy-D-phenylglycine derivatives, providing the correspoinding oxidative products.