(THIO)-SUBSTITUTED-1,4-BENZOQUINONES: SYNTHESIS, ELECTROCHEMISTRY, DFT CALCULATIONS, AND POTENTIAL ANTIPROLIFERATIVE EFFECT AGAINST MDA-MB-231 CELLS (ТИО)-СУПСТИТУИРАНИ-1,4-БЕНЗОХИНОНИ: СИНТЕЗА, ЕЛЕКТРОХЕМИЈА, DFT ПРЕСМЕТКИ И ПОТЕНЦИЈАЛЕН АНТИПРОЛИФЕРАТИВЕН ЕФЕКТ ПРОТИВ КЛЕТКИ НА MDA-MB-231

KAÇMAZ A., TÜRKER ACAR E., Atun G., HAMURCU Z.

Macedonian Journal of Chemistry and Chemical Engineering, vol.44, no.1, pp.1-11, 2025 (SCI-Expanded, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 44 Issue: 1
  • Publication Date: 2025
  • Doi Number: 10.20450/mjcce.2025.3016
  • Journal Name: Macedonian Journal of Chemistry and Chemical Engineering
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Directory of Open Access Journals
  • Page Numbers: pp.1-11
  • Keywords: benzoquinones, p-chloranil, thiols, time-dependent density functional theory
  • Erciyes University Affiliated: Yes

Abstract

This study explores the synthesis, electrochemical properties, and computational aspects of mono-, bis-, tris-, and tetrakis(thio)-substituted 1,4-benzoquinones. The electrochemical properties of the com pounds were analyzed using staircase cyclic voltammetry (CV). Ground-state energies were determined through time-dependent density functional theory (TD-DFT), utilizing the B3LYP functional and the 6 311G(d,p) basis set. Additionally, the in vitro anticancer efficacy of 2-(tert-butylthio)-3,5,6-trichloro cyclohexa-2,5-diene-1,4-dione (compound 5) was evaluated using the triple-negative breast cancer cell line (MDA-MB-231). Notably, compound 5 demonstrated significant potency, with values of 50 µM 50% cytotoxic concentration (IC50).