Current Chemistry Letters (Jan 2023)

Synthesis and antioxidant activity evaluation of some new 4-thiomethyl functionalised 1,3-thiazoles

  • Ivanna Danyliuk,
  • Nataliia Kovalenko,
  • Valentyna Tolmachova,
  • Olena Kovtun,
  • Lesya Saliyeva,
  • Nataliia Slyvka,
  • Serhii Holota,
  • Gennady Kutrov,
  • Magdalina Tsapko,
  • Mykhailo Vovk

DOI
https://doi.org/10.5267/j.ccl.2023.6.002
Journal volume & issue
Vol. 12, no. 4
pp. 667 – 676

Abstract

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The 4-bromomethyl-substituted thiazolium salts and corresponding thiazoles obtained through the condensation of 1,3-dibromoacetone with thioamide derivatives were utilised as efficient alkylating reagents for a series of thiophenols and heterylthiols. As a result, a small library of 4-thiomethyl-functionalised 1,3-thiazoles was synthesised in high yields, and their structures were characterised by 1H, 13C NMR, LC-MS and IR spectra. Antioxidant activity of obtained compounds was studied in vitro using the DPPH test. The synthesised compounds showed high absorption level of DPPH radicals in the 70-98% range. For the most active derivatives 7e,m,p,t IC50 values were determined, which were in the range 191-417 µM (for ascorbic acid (reference) IC50 value was 29 µM). Obtained radical scavenging activity screening data suggest in-depth study of the antioxidant potential for these types of heterocyclic compounds.