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Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres.

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).

SUBMITTER: Mattio LM

PROVIDER: S-EPMC8703454 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres.

Mattio Luce Micaela LM Pinna Cecilia C Catinella Giorgia G Musso Loana L Pedersen Kasandra Juliet KJ Krogfelt Karen Angeliki KA Dallavalle Sabrina S Pinto Andrea A

Molecules (Basel, Switzerland) 20211215 24

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 ...[more]

PMID: 34946674

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