98778-82-6Relevant academic research and scientific papers
Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives
Pastrana Restrepo, Manuel,Galeano Jaramillo, Elkin,Martínez Martínez, Alejandro,Robledo Restrepo, Sara
, p. 2454 - 2465 (2018/10/02)
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
Restrepo, Manuel Pastrana,Jaramillo, Elkin Galeano,Martínez, Alejandro Martínez,Arango, Ana Mesa,Restrepo, Sara Robledo
, p. 2569 - 2579 (2018/11/06)
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.
Bromotyrosine alkaloids from the Australian marine sponge Pseudoceratina verrucosa
Tran, Trong D.,Pham, Ngoc B.,Fechner, Gregory,Hooper, John N. A.,Quinn, Ronald J.
, p. 516 - 523 (2013/06/05)
Two new bromotyrosine alkaloids, pseudoceralidinone A (1) and aplysamine 7 (2), along with three known compounds were isolated from the Australian sponge Pseudoceratina verrucosa. Their structures were characterized by NMR and MS data and the synthetic ro
Organic Chemistry of L-Tyrosine. 1. General Synthesis of Chiral Piperazines from Amino Acids
Jung, Michael E.,Rohloff, John C.
, p. 4909 - 4913 (2007/10/02)
A new method for the conversion of optically active diketopiperazines (cyclo-dipeptides) into optically pure piperazines is described.Due to poor solubility of certain cyclo-dityrosine derivatives, the usual method using lithium aluminum hydride reaction was problematic, giving racemization under forcing conditions.However, the use of borane/tetrahydrofuran for this diketopiperazine to piperazine reduction proceeded well, affording high yields of optically pure materials.In this manner several mixed cyclo-dityrosine derivatives 9a-d were transformed into the piperazines 10a-d, potentially useful intermediates for the synthesis of the antibiotic alkaloids, piperazinomycin (1) and herquline (2).Finally, the naturally occuring alkaloid isolated from Zanthoxylum arborescens, 7b was prepared by this route.
