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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.
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]
Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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Header DbId: egs
DbLabel: Engineering Source
An: 181158164
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
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  Data: 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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  Data: <searchLink fieldCode="AR" term="%22Saha%2C+Anay%22">Saha, Anay</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Roy%2C+Keya%22">Roy, Keya</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Banerjee%2C+Subhrajyoti%22">Banerjee, Subhrajyoti</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Panja%2C+Subir%22">Panja, Subir</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Khatua%2C+Manas%22">Khatua, Manas</searchLink><relatesTo>4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Mukhopadhyay%2C+Chitrangada+Das%22">Mukhopadhyay, Chitrangada Das</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Samanta%2C+Subhas%22">Samanta, Subhas</searchLink><relatesTo>4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Adak%2C+Laksmikanta%22">Adak, Laksmikanta</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> ladak@chem.iiests.ac.in</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. Feb2025:Part 1, Vol. 1322, pN.PAG-N.PAG. 1p.
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  Data: <searchLink fieldCode="DE" term="%22Antifungal+agents%22">Antifungal agents</searchLink><br /><searchLink fieldCode="DE" term="%22Transformation+groups%22">Transformation groups</searchLink><br /><searchLink fieldCode="DE" term="%22Antineoplastic+agents%22">Antineoplastic agents</searchLink><br /><searchLink fieldCode="DE" term="%22Biochemical+substrates%22">Biochemical substrates</searchLink><br /><searchLink fieldCode="DE" term="%22Functional+groups%22">Functional groups</searchLink><br /><searchLink fieldCode="DE" term="%22Diamides%22">Diamides</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: • 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]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1016/j.molstruc.2024.140177
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      – Code: eng
        Text: English
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        PageCount: 1
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      – SubjectFull: Antifungal agents
        Type: general
      – SubjectFull: Transformation groups
        Type: general
      – SubjectFull: Antineoplastic agents
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      – SubjectFull: Biochemical substrates
        Type: general
      – SubjectFull: Functional groups
        Type: general
      – SubjectFull: Diamides
        Type: general
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      – TitleFull: 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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            NameFull: Saha, Anay
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              M: 02
              Text: Feb2025:Part 1
              Type: published
              Y: 2025
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