355857-30-6Relevant articles and documents
Psammaplin A derivative as well as preparation method and application thereof
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Paragraph 0044; 0048; 0058-0062, (2021/04/21)
The invention provides a Psammaplin A derivative as well as a preparation method and application thereof, and belongs to the field of medicinal chemistry, wherein the Psammaplin A derivative has a structural formula represented by a formula (I), wherein in the formula, R1, R2, R3, R4, R5 and R6 are respectively selected from any one of H, OH, OCH3, Br, 3,5-di-fluoro-benzyloxy, 2-fluoro-benzyloxy, 3-fluoro-benzyloxy, 4-cyano-benzyloxy and 4-trifluoromethyl-benzyloxy; R1 and R4 are the same or different, R2 and R5 are the same or different, and R3 and R6 are the same or different. According to the invention, a new structure and thought are provided for the design of a novel HDAC inhibitor, and the developed Psammaplin A derivative has a good anti-tumor cytotoxicity effect, and also provides an important theoretical reference for the development of HDAC-based anti-tumor drugs.
Synthetic C6-Functionalized Aminoflavin Catalysts Enable Aerobic Bromination of Oxidation-Prone Substrates
Storch, Golo,Walter, Alexandra
supporting information, p. 22505 - 22509 (2020/10/12)
Flavoenzymes catalyze oxidations via hydroperoxide intermediates that result from activation of molecular O2. These reactions—such as hydroxylation and halogenation—depend on the additional catalytic activity of functional groups in the peptide
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.
Syntheses of pseudoceramines A-D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges
Hillgren, J. Mikael,Oeberg, Christopher T.,Elofsson, Mikael
experimental part, p. 1246 - 1254 (2012/03/07)
Herein we report the total syntheses of pseudoceramine A-D (2-5) and spermatinamine (1) isolated from the marine sponge Pseudoceratina sp. Direct acyl substitution of α-hydroxyiminoesters with amine nucleophiles was developed as a key transformation. The synthetic compounds confirm the reported structures and importantly gives access to non-symmetrical spermine based natural products carrying two different bromotyrosine building blocks. Our new synthesis of spermatinamine is two steps shorter and more efficient than the previously reported sequence. The Royal Society of Chemistry 2012.
Characterization of thyroid hormone receptor α (TRα)-specific analogs with varying inner- and outer-ring substituents
Ocasio, Cory A.,Scanlan, Thomas S.
, p. 762 - 770 (2008/09/17)
Analogs of the TRα-specific thyromimetic CO23 were synthesized and analyzed in vitro using competitive binding and transactivation assays. Like CO23, all analogs bind to both thyroid hormone receptor subtypes with about the same affinity; however, modification of CO23 by derivatization of the 3′ position of the outer-ring or replacement of the inner-ring iodides with bromides attenuates binding. Despite lacking a preference in binding to TRα, all analogs display TRα-specificity in transactivation assays using U2OS and HeLa cells. At best, several agonists exhibit an approximately 6-12-fold preference in transactivation when tested with TRα in HeLa cells. One analog, CO24, showed in vivo TRα-specific action in a tadpole metamorphosis assay.
