Facile One-Pot Conversion of (poly)phenols to Diverse (hetero)aryl Compounds by Suzuki Coupling Reaction: A Modified Approach for the Synthesis of Coumarin- and Equol-Based Compounds as Potential Antioxidants.

Muthipeedika Nibin Joy, Igor S Kovalev, Olga V Shabunina, Sougata Santra, Grigory V Zyryanov

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Article in Antioxidants (Basel, Switzerland), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

Muthipeedika Nibin JoyUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira Street, Yekaterinburg 620002, Russia.ORCID 0000-0002-9912-2264

Igor S KovalevUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira Street, Yekaterinburg 620002, Russia.ORCID 0000-0002-0537-3274

Olga V ShabuninaUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira Street, Yekaterinburg 620002, Russia.

Sougata SantraUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira Street, Yekaterinburg 620002, Russia.

Grigory V ZyryanovUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira Street, Yekaterinburg 620002, Russia.

Funding

Ministry of Science and Higher Education of the Russian Federation Reference # 075-15-2022-1118, dated 29 June 2022Russian Science Foundation Grant # 24-23-00516

6 · The paper itself

Abstract

A series of 16 (hetero)aryl compounds based on coumarin and equol has been efficiently synthesized by exploring the palladium-catalyzed Suzuki cross-coupling reactions. Polyphenol based on coumarin (4-methyl-7-hydroxy coumarin) was initially converted to corresponding coumarin imidazylate and then subjected to Suzuki coupling reaction with 4-methoxyphenylboronic acid to obtain the coupled product. This modified approach was later developed into a one-pot methodology by directly reacting the polyphenol with 1,1-sulfonyldiimidazole (SDI) and boronic acid in situ to obtain the Suzuki coupled product in one step. Moreover, an array of (poly)phenols based on coumarin and equol were later converted to diverse (hetero)aryl compounds by this optimized step-economic protocol. The synthesized compounds were then subjected to the screening of their potential antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In our investigation, the compounds

Indexed as

antioxidantsaryl imidazylatescoumarinDPPHSuzuki coupling

Identifiers

PMID39456452

DOI10.3390/antiox13101198

PMCPMC11504026

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