Room temperature palladium-catalyzed synthesis of novel unsymmetrical diamide scaffolds containing moieties of α-ketoester as potential antibacterial, antifungal and anticancer agents.
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| Title: | Room temperature palladium-catalyzed synthesis of novel unsymmetrical diamide scaffolds containing moieties of α-ketoester as potential antibacterial, antifungal and anticancer agents. |
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| Authors: | Saha, Anay1 (AUTHOR), Roy, Keya1 (AUTHOR), Banerjee, Subhrajyoti2 (AUTHOR), Panja, Subir3 (AUTHOR), Khatua, Manas4 (AUTHOR), Mukhopadhyay, Chitrangada Das2 (AUTHOR), Samanta, Subhas4 (AUTHOR), Adak, Laksmikanta1 (AUTHOR) ladak@chem.iiests.ac.in |
| Source: | Journal of Molecular Structure. Feb2025:Part 1, Vol. 1322, pN.PAG-N.PAG. 1p. |
| Subjects: | Antifungal agents, Transformation groups, Antineoplastic agents, Biochemical substrates, Functional groups, Diamides |
| Abstract: | • Synthesis of a new series of unsymmetrical diamide scaffolds containing α-ketoester moieties. • A mild (room temperature), ligand- and additive-free and atom-economic palladium-catalyzed reaction. • High yields of isolated products, tolerance to several sensitive functionalities (including heterocycles) and molecules. • The synthesized products were confirmed by spectroscopic techniques and X-ray crystallographic analysis. • Significant antibacterial, antifungal, and anticancer properties of synthesized novel products. Given the widespread use of diamides and α-ketoesters in chemistry and biology and valuable precursors in various functional group transformations, developing methods for their synthesis remains essential. We have developed for the first time a novel atom-economic, mild, and efficient palladium-catalyzed reaction of a range of diversely substituted amide oxazolines 1 with various glyoxylic acid 2 for the synthesis of a new series of unsymmetrical diamide scaffolds containing α-ketoester moieties. This method provided the products with high yields, and the synthesized products were confirmed by spectroscopic techniques (e.g., FT-IR, 1H NMR, 13C NMR, HRMS spectroscopy) and X-ray crystallographic analysis. The synthesized novel products, 2-(2-benzamidobenzamido)ethyl 2-oxo-2-arylacetate derivatives (3i and 3r) have been evaluated in-vitro for their antibacterial, antifungal and anticancer activities, and it was found that both the prepared compounds showed significant antibacterial, antifungal and anticancer properties. [Display omitted] [ABSTRACT FROM AUTHOR] |
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| Database: | Engineering Source |
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