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

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

Molecules (Basel, Switzerland) 2021 Dec 15

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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).

Citation

Luce Micaela Mattio, Cecilia Pinna, Giorgia Catinella, Loana Musso, Kasandra Juliet Pedersen, Karen Angeliki Krogfelt, Sabrina Dallavalle, Andrea Pinto. Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres. Molecules (Basel, Switzerland). 2021 Dec 15;26(24)