Ionic-Liquid-Supported Synthesis of Amines and Derivatives

International audienceAmine precursors such as glycines protected at nitrogen with a Boc or formyl group were grafted by esterification on the hydroxylated arms of 1-(2-hydroxyethyl)-3-methylimidazolium hexafluorophosphates or tetrafluoroborates. The cleavage of the Boc group was then realized at room temperature by successively treating acetonitrile solutions of the thus formed glycinates with methanol and acetyl chloride (two equivalents each). Interestingly, the resulting glycinate hydrochlorides were converted into the corresponding amines during the removal of the solvent. Ugi reaction of one of these ionic-liquid-grafted amines with phthalaldehydic acid and tert-butyl isocyanide, followed by cleavage, furnished a phthalimidine 12

Synthesis, Thermal, DFT Calculations, HOMO-LUMO, MEP, and Molecular Docking Analysis of New Derivatives of Imidazolin-4-Ones

This work focuses on synthesizing new imidazolin-4-one derivatives (2a-c), akin to leucettamine B analogs, via microwave-assisted transamination reactions. This reaction was carried out between 3-alkyl-5-dimethylamino-2-thioxo-imidazolidin-4-one (1a-c) and aniline. The structural integrity of the synthesized compounds was confirmed using NMR and MS spectroscopy, and their configurations were validated through DFT calculations. Analyses encompassed molecular electrostatic potential, frontier molecular orbitals, HOMO-LUMO energies, energy band gap, and global chemical reactivity descriptors, providing comprehensive insights into their characteristics. The investigation extended to the biological domain, employing substance activity spectra prediction (PASS) and molecular docking with Autodock Vina4 program. Notably, this holistic assessment aimed to gauge the potential regulatory effect of the compounds on cholesterol. This integrated approach contributes to compound design understanding and potential applications, spanning drug design and broader biomedical contexts

Bioactive Dehydrotyrosyl and Dehydrodopyl Compounds of Marine Origin

The amino acid, tyrosine, and its hydroxylated product, 3,4-dihydroxyphenylalanine (dopa), plays an important role in the biogenesis of a number of potentially important bioactive molecules in marine organisms. Interestingly, several of these tyrosyl and dopa-containing compounds possess dehydro groups in their side chains. Examples span the range from simple dehydrotyrosine and dehydrodopamines to complex metabolic products, including peptides and polycyclic alkaloids. Based on structural information, these compounds can be subdivided into five categories: (a) Simple dehydrotyrosine and dehydrotyramine containing molecules; (b) simple dehydrodopa derivatives; (c) peptidyl dehydrotyrosine and dehydrodopa derivatives; (d) multiple dehydrodopa containing compounds; and (e) polycyclic condensed dehydrodopa derivatives. These molecules possess a wide range of biological activities that include (but are not limited to) antitumor activity, antibiotic activity, cytotoxicity, antioxidant activity, multidrug resistance reversal, cell division inhibition, immunomodulatory activity, HIV-integrase inhibition, anti-viral, and anti-feeding (or feeding deterrent) activity. This review summarizes the structure, distribution, possible biosynthetic origin, and biological activity, of the five categories of dehydrotyrosine and dehydrodopa containing compounds

Application de l’ACP à une base de données de liquides ioniques

L’objectif de cette étude est de mettre en évidence le facteur le plus influant sur la conductivité électrique d’un liquide ionique en appliquant l’analyse en composantes principales (ACP). Pour atteindre cet objectif nous avons utilisé le logiciel XLSTAT que nous avons appliqué à une base de données de 500 liquides ioniques différents. Pour chaque liquide ionique,une dizaine de propriétés physico-chimiques sont répertoriées. Il ressort de cette étude que les liquides ioniques présentant une forte conductivité électrique sont caractérisés par une faible température de transition vitreuse, une forte température de cristallisation et un faible indice de réfraction. La conductivité d’un liquide ionique augmente avec la taille de l’anion et diminue avec l’augmentation de la taille du catio

Synthesis and preliminary biological evaluation of new derivatives of the marine alkaloid leucettamine B as kinase inhibitors.

International audienceNew derivatives of the marine alkaloid leucettamine B were prepared in five steps with overall yields ranging from 23 to 30%. The key step of our strategy has been the sulfur/nitrogen displacement under solvent-free microwave irradiation of (5Z) 5-benzo[1,3]-dioxo-5-ylmethylene-2-ethylsulfanyl-3,5-dihydroimidazol-4-one 3 with a mono-protected ethylenediamine 2. After deprotection of the N-Boc group, the amino derivative of leucettamine B 5 was subjected to reductive amination in two steps with retention of configuration of the double bond, to lead to eight new analogs of leucettamine B. The effect of these compounds on CK1alpha/beta, CDK5/p25, and GSK-3alpha/beta were investigated

An efficient method for the preparation of new analogs of Leucettamine B under solvent-free microwave irradiation.

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Synthesis and Structural Characterization of Imidazolium-Based Dicationic Ionic Liquids

Dicationic ionic liquids present a novel class of ionic liquids composed of dication and two monoanions; the latter have shown an increasing interest in recent years and are used in many applications. Compared to conventional ionic liquids, the physicochemical properties of dicationic ionic liquids can be set by modifying the languor and the type of chains linking the cationic heads as well as the type of cation. In this work, we present the synthesis of three dicationic ionic liquids based on imidazolium with two steps; the first of which is a quaternization reaction leading to the formation of dicationic ionic liquids with the iodide ion. The characterization of these organic salts was carried out by magnetic resonance spectroscopy, allowing a better identification of the products obtained