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).

Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres / L. Micaela Mattio, C. Pinna, G. Catinella, L. Musso, K. Juliet Pedersen, K. Angeliki Krogfelt, S.M.D. Dallavalle, A. Pinto. - In: MOLECULES. - ISSN 1420-3049. - 26:24(2021 Dec 15), pp. 7594.1-7594.10. [10.3390/molecules26247594]

Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres

C. Pinna
Secondo
;
G. Catinella;L. Musso;S.M.D. Dallavalle
Penultimo
;
A. Pinto
Ultimo
2021

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).
viniferin derivatives; stilbenoids; benzofuran nucleus; antimicrobials;
Settore CHIM/10 - Chimica degli Alimenti
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890501
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