782440-99-7

Upstream product

• 1080-06-4 L-Tyr-OMe 
• 60-18-4 L-tyrosine 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 232277-27-9 methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate 

Downstream Products

• 232277-27-9 methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate 
• 7423-93-0 (S)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid 
• 192315-37-0 (S)-methyl 3-(3-chloro-4-methoxyphenyl)-2-(tert-butoxycarbonylamino)propanoate 
• 1314789-46-2 (E)-3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanoic acid 
• 1314789-34-8 (E)-methyl 3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanoate 
• 185687-97-2 (S)-3-(3-Bromo-5-chloro-4-hydroxy-phenyl)-2-[(R)-2-[(R)-2-tert-butoxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(4-methoxy-phenyl)-acetylamino]-propionic acid methyl ester 
• 185687-99-4 (8R,11R,14S)-19-Bromo-8-tert-butoxycarbonylamino-18-chloro-4-hydroxy-5-iodo-11-(4-methoxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester 

Relevant academic research and scientific papers

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.

TTN oxidation of mixed halogenated phenols: Synthesis of vancomycin model diaryl ether possessing a chlorine atom

The diaryl ether possessing a chlorine atom has been synthesized as a model study on a synthesis of vancomycin class glycopeptide antibiotics. Thallium (III) oxidation of the bisphenol derivative followed by selective reduction provided the corresponding cyclic product in moderate overall yield. Conformation of the products is also discussed.