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<p>The reaction of 3,5-di-<i>tert</i>-butyl-6-(metoxymethyl)catechol with 1,3-dicarbonyl compounds afforded new 2,8-dihydroxychromane derivatives with a sterically hindered phenolic fragment. Dehydration of the resulting compounds led to 8-hydroxy-4<i>H</i>-chromene derivatives. A heterocyclic analog of the [4.4.4]propellane structure was obtained by double addition of <i>o</i>-quinone methide to indanedione. The electrochemical properties of the new compounds, as well as their radical-scavenging activity in the DPPH and CUPRAC assays, were studied. Some of test compounds demonstrated efficiency exceeding or comparable to that of Trolox. Moderate cytotoxicity toward several human cancer cell lines was also established.</p>

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Sterically hindered 2,8-dihydroxychromanes and 8-hydroxy-4H-chromenes: synthesis, properties, and radical-scavenging activity

  • 期刊论文

  • 发表日期：

    2026年1月1日

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  • A. A. Pashkov,
  • D. A. Martynova,
  • T. A Kovylina,
  • N. M. Khamaletdinova,
  • A. E. Tarakanova,
  • A. V. Bogdanov,
  • A. D. Voloshina,
  • M. V. Arsenyev,
  • S. A. Chesnokov

摘要

The reaction of 3,5-di-tert-butyl-6-(metoxymethyl)catechol with 1,3-dicarbonyl compounds afforded new 2,8-dihydroxychromane derivatives with a sterically hindered phenolic fragment. Dehydration of the resulting compounds led to 8-hydroxy-4H-chromene derivatives. A heterocyclic analog of the [4.4.4]propellane structure was obtained by double addition of o-quinone methide to indanedione. The electrochemical properties of the new compounds, as well as their radical-scavenging activity in the DPPH and CUPRAC assays, were studied. Some of test compounds demonstrated efficiency exceeding or comparable to that of Trolox. Moderate cytotoxicity toward several human cancer cell lines was also established.