Synthesis of Indole-, Benzo[<i>b</i>]thiophene-, and Benzo[<i>b</i>]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B

Krzyzanowski, Adrian; Saleeb, Michael; Elofsson, Mikael

doi:10.1021/acs.orglett.8b02638

Cited by 13 publications

(9 citation statements)

References 40 publications

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“…Several troublesome efforts in the demethylation process confirmed that this step is an Achilles' heel in the synthesis of stilbenoids-derived compounds [6,10,14,22].…”

Section: Resultsmentioning

confidence: 94%

“…Over the last years, several efforts were made towards the synthesis of complex natural resveratrol oligomers, by biomimetic and de novo approaches [1,[5][6][7][8][9]. However, only few research groups have focused on the synthesis of new resveratrol-derived chemical scaffolds with improved pharmacodynamics and pharmacokinetics with respect to the natural precursors [6,[10][11][12][13][14]. In this scenario, we planned to set up a versatile and efficient synthetic strategy for the construction of dimeric resveratrol-derived benzofurans.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres

et al. 2021

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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).

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“…Several troublesome efforts in the demethylation process confirmed that this step is an Achilles' heel in the synthesis of stilbenoids-derived compounds [6,10,14,22].…”

Section: Resultsmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres

et al. 2021

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“…In addition to normal RSV reactions, another method for preparing RSV and its derivatives was discovered. RSV and its products were synthesized via the Horner-Wadsworth-Emmons reaction, and it was found that certain substances had a discerning capacity to inhibit cyclooxygenase-1 and cyclooxygenase-2 [49]. RSV from grapevine leaves was obtained by aluminum chloride induction.…”

Section: Chemical Synthesis Of Resveratrolmentioning

confidence: 99%

A Comprehensive Study on the Antimicrobial Properties of Resveratrol as an Alternative Therapy

Abedini

Khodadadi

Zeinalzadeh

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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Resveratrol is a polyphenolic antioxidant whose possible health benefits include anticarcinogenic, antiaging, and antimicrobial properties that have gained significant attention. The compound is well accepted by individuals and has been commonly used as a nutraceutical in recent decades. Its widespread usage makes it essential to study as a single agent as well as in combination with traditional prescription antibiotics as regards to antimicrobial properties. Resveratrol demonstrates the action of antimicrobials against a remarkable bacterial diversity, viruses, and fungus. This report explains resveratrol as an all-natural antimicrobial representative. It may modify the bacterial virulence qualities resulting in decreased toxic substance production, biofilm inhibition, motility reduction, and quorum sensing disturbance. Moreover, in conjunction with standard antibiotics, resveratrol improves aminoglycoside efficacy versus Staphylococcus aureus, while it antagonizes the deadly function of fluoroquinolones against S. aureus and also Escherichia coli. The present study aimed to thoroughly review and study the antimicrobial potency of resveratrol, expected to help researchers pave the way for solving antimicrobial resistance.

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“…Since then, these protocols have paved the way for the development of several transformations in organic synthesis. For instance, this was the key step in the recently-described synthesis of benzo[b]selenophene-based analogues of the resveratrol dimers viniferifuran and (±)-dehydroampelopsin B (Scheme 39) [147]. The 5-endo-dig cyclization was carried out under microwave irradiation, in just 75 min, using I 2 as an electrophile and DCM as a solvent, affording the 3-iodo-selenophene 53 in 96% yield.…”

Section: Scheme 38mentioning

confidence: 99%

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

et al. 2020

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The selenophene derivatives are an important class of selenium-based heterocyclics. These compounds play an important role in prospecting new drugs, as well as in the development of new light-emitting materials. During the last years, several methods have been emerging to access the selenophene scaffold, employing a diversity of cyclization-based synthetic strategies, involving specific reaction partners and particularities. This review presents a comprehensive discussion on the recent advances in the synthesis of selenophene-based compounds, starting from different precursors, highlighting the main differences, the advantages, and limitations among them.

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Synthesis of Indole-, Benzo[b]thiophene-, and Benzo[b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B

Cited by 13 publications

References 40 publications

Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres

Synthesis and Antimicrobial Activity of δ-Viniferin Analogues and Isosteres

A Comprehensive Study on the Antimicrobial Properties of Resveratrol as an Alternative Therapy

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

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