69358-28-7Relevant academic research and scientific papers
Derivatives of tenuazonic acid as potential new multi‐target anti‐alzheimer’s disease agents
Poliseno, Viviana,Chaves, Sílvia,Brunetti, Leonardo,Loiodice, Fulvio,Carrieri, Antonio,Laghezza, Antonio,Tortorella, Paolo,Magalh?es, Jo?o D.,Cardoso, Sandra M.,Santos, M. Amélia,Piemontese, Luca
, p. 1 - 23 (2021)
Alzheimer’s disease (AD) is generally recognized as a multifactorial neurodegenerative pathology with an increasing impact on society. Tenuazonic acid (TA) is a natural compound that was recently identified as a potential multitarget ligand with anti‐cholinesterase, anti-amyloidogenic and antioxidant activities. Using its structure as a chemical scaffold, we synthesized and evaluated new derivatives (1–5), including tenuazonic‐donepezil (TA‐DNP) hybrids (4 and 5) due to the clinical importance of the anti‐AD drug donepezil. These novel compounds all achieved activity in the micromolar range towards all selected targets and demonstrated to be potentially orally absorbed. Moreover, a selected compound (1) was further investigated as a chelating agent towards copper (II), zinc (II) and iron (III) and showed good chelating ability (pFe = 16.6, pCu = 11.6, pZn = 6.0 at pH 7.4). Therefore, the TA motif can be considered an interesting building block in the search for innovative multi‐functional anti‐neurodegenerative drugs, as exemplified by hybrid 5, a promising non‐cytotoxic lead compound adequate for the early stages of AD, and capable of ameliorating the oxidative status of SH‐SY5Y human neuroblastoma cells.
Tetramic Acid Chemistry. Part 1. Reinvestigation of Racemisation during the Synthesis of Tetramic Acids via Dieckmann Cyclisation
Poncet, Joel,Jouin, Patrick,Castro, Bertrand,Nicolas, Louisette,Boutar, Mohamed,Gaudemer, Alain
, p. 611 - 616 (2007/10/02)
Epimerisation during the synthesis of tetramic acids by Dieckmann cyclisation of the corresponding chiral N-acyl-α-amino esters was investigated.In the case of the isoleucine derivative, the extent of epimerisation was directly evaluated by 1H NMR analysis of the 3-acylated tetramic acids (3a,b) and (5a).A chemical correlation was carried out in the case of the 5-benzyl derivative (8h).The moderate overall yield and the partial epimerisation at position C-5 limit the usefulness of this approach for tetramic acid preparation.
Acetylation of Pyrrolidine-2,4-diones: A Synthesis of 3-Acyltetramic Acids. X-Ray Molecular Structure of 3--5-isopropyl-1-methylpyrrolidine-2,4-dione
Jones, Raymond C. F.,Begley, Michael J.,Peterson, Graeme E.,Sumaria, Suresh
, p. 1959 - 1968 (2007/10/02)
Pyrrolidine-2,4-diones, prepared from the corresponding α-amino acid esters by condensation with ethoxycarbonylacetic acid, Dieckmann cyclisation, and hydrolysis-decarboxylation, are acylated at C-3 by the acid chlorides of saturated, unsaturated, and are
