Synthesis and antimicrobial activity of δ-viniferin analogues and isosteres

Luce Micaela Mattio, Cecilia Pinna, Giorgia Catinella, Loana Musso, Karen Angeliki Krogfelt, Sabrina Dallavalle*, Andrea Pinto

*Corresponding author

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Abstract

The natural stilbenoid dehydro-δ-viniferin, containing a benzofuran core, has been recently identified as a promising antimicrobial agent. To define the structural elements relevant to its activity, we modified the styryl moiety, appended at C5 of the benzofuran ring. In this paper, we report the construction of stilbenoid-derived 2,3-diaryl-5-substituted benzofurans, which allowed us to prepare a focused collection of dehydro-δ-viniferin analogues. The antimicrobial activity of the synthesized compounds was evaluated against S. aureus ATCC29213. The simplified analogue 5,5-(2-(4-hydroxyphenyl)benzofuran-3,5-diyl)bis(benzene-1,3-diol), obtained in three steps from 4-bromo-2-iodophenol (63% overall yield), emerged as a promising candidate for further investigation (MIC = 4 µg/mL).

OriginalsprogEngelsk
Artikelnummer7594
TidsskriftMolecules
Vol/bind26
Udgave nummer24
ISSN1420-3049
DOI
StatusUdgivet - 1 dec. 2021

Bibliografisk note

Funding Information:
Acknowledgments: This work was financially supported by “Transition Grant 2015–2017-Linea 1A” of the University of Milan.

Emneord

  • Antimicrobials
  • Benzofuran nucleus
  • Stilbenoids
  • Viniferin derivatives

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