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

doi:10.3390/molecules26247594

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

^*Corresponding author

Institut for Naturvidenskab og Miljø

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer 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).

Originalsprog	Engelsk
Artikelnummer	7594
Tidsskrift	Molecules
Vol/bind	26
Udgave nummer	24
ISSN	1420-3049
DOI	https://doi.org/10.3390/molecules26247594
Status	Udgivet - 1 dec. 2021

Emneord

Antimicrobials
Benzofuran nucleus
Stilbenoids
Viniferin derivatives

Link til dokument

10.3390/molecules26247594Licens: CC BY

Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres Forlagets udgivne version, 2,38 MBLicens: CC BY

Citer dette

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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).",

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AU - Mattio, Luce Micaela

AU - Pinna, Cecilia

AU - Catinella, Giorgia

AU - Musso, Loana

AU - Pedersen, Kasandra Juliet

AU - Krogfelt, Karen Angeliki

AU - Dallavalle, Sabrina

AU - Pinto, Andrea

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N2 - 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).

AB - 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).

KW - Antimicrobials

KW - Benzofuran nucleus

KW - Stilbenoids

KW - Viniferin derivatives

KW - Antimicrobials

KW - Benzofuran nucleus

KW - Stilbenoids

KW - Viniferin derivatives

U2 - 10.3390/molecules26247594

DO - 10.3390/molecules26247594

M3 - Journal article

AN - SCOPUS:85121518657

SN - 1420-3049

VL - 26

JO - Molecules

JF - Molecules

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