173383-29-4

Basic information

• Product Name: 3,5-DIBROMO-D-TYROSINE METHYL ESTER
• Synonyms: 3,5-DIBROMO-D-TYROSINE METHYL ESTER;H-3,5-DIBROMO-D-TYR-OME;METHYL (2R)-2-AMINO-3-(3,5-DIBROMO-4-HYDROXYPHENYL)PROPANOATE;(R)-Methyl 2-aMino-3-(3,5-dibroMo-4-hydroxyphenyl)propanoate
• CAS NO: 173383-29-4
• Molecular Formula: C10H11Br2NO3
• Molecular Weight: 353.01
• Mol File: 173383-29-4.mol

Chemical Properties

• Boiling Point: 372.8°C at 760 mmHg
• Flash Point: 179.3°C
• Appearance: /
• Density: 1.823g/cm³
• Vapor Pressure: 4.35E-06mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,5-DIBROMO-D-TYROSINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIBROMO-D-TYROSINE METHYL ESTER(173383-29-4)
• EPA Substance Registry System: 3,5-DIBROMO-D-TYROSINE METHYL ESTER(173383-29-4)

Safety Data

• Hazardous Substances Data: 173383-29-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11Br2NO3/c1-16-10(15)8(13)4-5-2-6(11)9(14)7(12)3-5/h2-3,8,14H,4,13H2,1H3/t8-/m1/s1

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 
• 355857-30-6 (+)-(S)-methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-(2-methylprop-2-yloxycarbamoyl)propanoate 
• 300-38-9 3,5-dibromo-L-tyrosine 
• 139517-75-2 (S)-methyl 2-(N-tert-butoxycarbonyl)(amino)-3-(3,5-dibromo-4-methoxyphenyl)propanoate 
• 173383-27-2 (R)-2-((R)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid 
• 862805-23-0 3,5-dibromo-N-{[4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidin-1-yl]carbonyl}-D-tyrosine 
• 204696-52-6 [(R)-(R*,S*)]-[5-[[3-(3,5-dibromo-4-hydroxyphenyl)-2-[[[4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl)-1-piperidinyl]carbonyl]amino]-1-oxopropyl]amino]-6-oxo-6-[4-(4-pyridinyl)-1-piperazinyl]hexyl]-carbamic acid 1,1-dimethylethyl ester 
• 173383-13-6 (S)-2-[(R)-2-((R)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-3-(3,5-dibromo-4-hydroxy-phenyl)-propionylamino]-succinamic acid 

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.

Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives

Twenty-two halogenated l-tyrosine derivatives were synthesized to examine new substances for the treatment of Chagas disease. The synthesis of these derivatives with different degree of substitution in the amino group with methyl iodide, giving primary, tertiary, and quaternary amino acids. All compounds were tested in vitro against intracellular amastigotes of Trypanosoma cruzi, and the cytotoxicity were evaluated over monocytic cell line U-937. Compound 25 was the most active against T. cruzi with a EC50 of 75.52 μM compared with benznidazole with a EC50 of 58.79 μM. Compounds 3, 4, 7, and 15 were the derivatives with the best selectivity index (SI) with values of 7.5, 8.3,12.1, and 8.6, respectively. Finally, compound 7 was the safer and the more promising derivative against T. cruzi.

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.

Macrocyclization by TTN Oxidation for the Synthesis of Chloropeptin Left-Hand Segment

Cyclic tripeptide containing a diphenylether bond of the Chloropeptin left-hand segment were synthesized with the use of TTN phenolic oxidation in high yield. They were found to exist as equilibrium mixtures of two stable conformers caused by a rotation o

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.

Pyridyl and pyridazinyl substituted thyronine compounds having selective thyromimetic activity

This invention relates to chemical compounds which have selective thyromimetic activity. A compound of this invention is 3,5-dibromo-3''-[6-oxo-3(1H)-pyridazinylmethyl]-thyronine.

Formation of Quinol Ethers using (Diacetoxyiodo)benzene

The use of (diacetoxyiodo)benzene for the oxidative coupling of a hindered phenol with aliphatic alcohols or other phenols has been investigated.