Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields and excellent enantio- and diastereoselectivities. The reaction conditions have been optimized by invoking ultrasonication and the influence of some structural moieties of the catalysts on the chemical yield and stereoselectivity of the Mannich products has been evaluated.
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http://dx.doi.org/10.1039/c3ob40681d | DOI Listing |
Acc Chem Res
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China.
ConspectusThe Mannich reaction, involving the nucleophilic addition of an enol(ate) intermediate to an imine or iminium ion, is one of the most widely used synthetic methods for the synthesis of β-amino carbonyl compounds. Nevertheless, the homo-Mannich reaction, which utilizes a homoenolate intermediate as the nucleophilic partner and provides straightforward access to the valuable γ-amino carbonyl compounds, remains underexplored. This can be largely attributed to the difficulties in generation and manipulation of the homoenolate species, despite various homoenolate equivalents that have been developed.
View Article and Find Full Text PDFFoods
December 2024
Instituto Universitario de Ingeniería de Alimentos-Food UPV, Universitat Politècnica de València, Camino de Vera s/n, 46022 Valencia, Spain.
The immobilisation of essential oil components (EOCs) on food-grade supports is a promising strategy for preserving liquid foods without the drawbacks of direct EOC addition such as poor solubility, high volatility, and sensory alterations. This study presents a novel method for covalently immobilising EOCs, specifically thymol and carvacrol, on SiO particles (5-15 µm) using the Mannich reaction. This approach simplifies conventional covalent immobilisation techniques by reducing the steps and reagents while maintaining antimicrobial efficacy and preventing compound migration.
View Article and Find Full Text PDFInt J Mol Sci
December 2024
Department of Chemistry, Faculty of Sciences, Canakkale Onsekiz Mart University, Terzioglu Campus, 17100 Canakkale, Turkey.
Hematoxylin (HT) is a natural staining dye used in histopathology, often combined with Eosin for H&E staining. A poly(hematoxylin-co-l-lysine) (p(HT-co-l)) nanonetwork was synthesized through a one-step Mannich condensation reaction using formaldehyde as a linking agent. The resulting p(HT-co-l) nanogels had an average size of about 200 nm and exhibited a smooth surface and desirable functional groups such as -OH, -NH, and -COOH, as recognized by FT-IR analysis.
View Article and Find Full Text PDFChemistryOpen
January 2025
Discipline of Pharmaceutical Sciences, Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban, 4000, South Africa.
An efficient microwave-assisted synthesis route for novel oxazolidinone analogues has been developed. The general synthesis of these compounds began with an L-proline-mediated three-component Mannich reaction between commercially available 3-fluoro-4-morpholinoaniline, aqueous formaldehyde and α-hydroxyacetone. This was followed by a one-step cyclisation to form the core structure of oxazolidinone antibiotics which was subsequently derivatized.
View Article and Find Full Text PDFBiomedicines
December 2024
Departamento de Ciência Básica, Instituto de Saúde de Nova Fribrugo, Universidade Federal Fluminense, Nova Friburgo 28625-650, RJ, Brazil.
Pyruvate kinase M2, a central regulator of cancer cell metabolism, has garnered significant attention as a promising target for disrupting the metabolic adaptability of tumor cells. This study explores the potential of the Mannich base derived from lawsone () to interfere with PKM2 enzymatic activity both in vitro and in silico. The antiproliferative potential of was tested using MTT assay in various cell lines, including SCC-9, Hep-G2, HT-29, B16-F10, and normal human gingival fibroblast (HGF).
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