113327-44-9Relevant 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.
SUBSTITUTED PHENYLALANINE DERIVATIVES
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Paragraph 0846; 0847; 0848; 0849, (2016/09/26)
The invention relates to substituted phenylalanine derivatives and to processes for preparation thereof, and to the use thereof for production of medicaments for the treatment and/or prophylaxis of diseases, especially of cardiovascular disorders and/or severe perioperative blood loss.
Improved synthesis of L,L-cycloisodityrosine subunit of antitumor agents deoxybouvardin and RA-VII
Ghosh, Samir,Kumar, A. Sanjeev,Mehta,Soundararajan
experimental part, p. 2389 - 2396 (2010/09/08)
A facile synthesis of the core cycloisodityrosine 14-membered ring system is detailed from commercially available L-tyrosine through a novel synthetic approach to aryl boronic acid 12 via intramolecular cyclization. Copyright Taylor & Francis Group, LLC.
Racemization in Suzuki couplings: A quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules
Prieto, Monica,Mayor, Silvia,Rodriguez, Katy,Lloyd-Williams, Paul,Giralt, Ernest
, p. 1047 - 1050 (2008/02/04)
(Chemical Equation Presented) Reaction conditions considered to be typical in Suzuki couplings can cause significant (up to 34% of the unwanted enantiomer) loss of optical purity in sensitive substrates such as hydroxyphenylglycine 1. This may be remedied using sodium succinate instead of sodium carbonate as base, but chemical yields are somewhat lower. Optically pure biaryl amino acids related to those found in the chloropeptins and vancomycin were synthesized by Suzuki coupling of 1 with indolylboronic acids 6-8 and with cyclic boronic acid 9.
Application of the Suzuki Biphenyl Synthesis to the Natural Products Biphenomycin and Vancomycin
Brown, Allan G.,Crimmin, Michael J.,Edwards, Peter D.
, p. 123 - 130 (2007/10/02)
The synthesis of the unsymmetrical biphenyls 10 and 25 has been carried out by the palladium(0) catalysed coupling of the aryl boronic derivatives 5 and 20 with the aryl bromides 9 and 23 derived from (R)-4-hydroxyphenylglycine and (S)-tyrosine.In the former case unsuccessful attempts were made to bring about cyclization to compound 4 which is an analogue of the biphenyl ring system found in vancomycin.In the latter case, a variety of cyclization methods were used to give the cyclic products 34 and 35 which are analogues of the biphenomycin antibiotics.
