2. Academic Validation
  3. Green Approach for the Synthesis of Chalcogenyl- 2,3-dihydrobenzofuran Derivatives Through Allyl-phenols/ Naphthols and Their Potential as MAO-B Inhibitors

Green Approach for the Synthesis of Chalcogenyl- 2,3-dihydrobenzofuran Derivatives Through Allyl-phenols/ Naphthols and Their Potential as MAO-B Inhibitors

  • Chem Asian J. 2023 Dec 14;18(24):e202300586. doi: 10.1002/asia.202300586.
Amanda R Azevedo 1,  Pâmella Cordeiro 1,  Dianer N Strelow 2,  Karine N de Andrade 3,  Marcos R S Neto 4,  Rodolfo Goetze Fiorot 3,  César A Brüning 2,  Antonio L Braga 4,  Luciano M Lião 5,  Cristiani F Bortolatto 2,  José S S Neto 5,  Vanessa Nascimento 1
Affiliations

Affiliations

  • 1 SupraSelen Laboratory, Department of Organic Chemistry, Universidade Federal Fluminense, Niterói, Institute of Chemistry, Campus do Valonguinho, 24020-141, RJ, Brazil.
  • 2 Molecular Biochemistry and Neuropharmacology Laboratory (LABIONEM), Chemical, Pharmaceutical and Food Sciences Center (CCQFA), Federal University of Pelotas Pelotas, 96010-900, RS, Brazil.
  • 3 Department of Organic Chemistry, Institute of Chemistry, Universidade Federal Fluminense Niterói, Outeiro São João Batista, s/n, 24020-141, RJ, Brazil.
  • 4 LabSelen, Department of Chemistry, Federal University of Santa Catarina, Santa Catarina, 88040-900, SC, Brazil.
  • 5 LabRMN, Chemistry Institute, Federal University of Goiás Goiânia, 74690-900, GO, Brazil.
PMID: 37733585 DOI: 10.1002/asia.202300586
Abstract

This work presents the design, synthesis, and MAO-B Inhibitor activity of a series of chalcogenyl-2,3-dihydrobenzofurans derivatives. Using solvent- and metal-free methodology, a series of chalcogen-containing dihydrobenzofurans 7-9 was obtained with yields ranging from 40% to 99%, using an I2 /DMSO catalytic system. All compounds were fully structurally characterized using 1 H and 13 C NMR analysis, and the unprecedented compounds were additionally analyzed using high-resolution mass spectrometry (HRMS). In addition, the mechanistic proposal that iodide is the most likely species to act in the transfer of protons along the reaction path was studied through theoretical calculations. Finally, the compounds 7b-e, 8a-e, and 9a showed great promise as inhibitors against MAO-B activity.

Keywords

dihydrobenzofurans; green synthesis; monoamines oxidases; organochalcogen.

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