Ungureanu Daniel, Marc Gabriel, Tiperciuc Brîndușa, Moldovan Cristina, Ionuț Ioana, Stana Anca, Oniga Ilioara, Vlase Laurian, Pîrnău Adrian, Oniga Ovidiu
Department of Pharmaceutical Chemistry, "Iuliu Hațieganu" University of Medicine and Pharmacy, 41 Victor Babeș Street, 400012 Cluj-Napoca, Romania.
Department of Organic Chemistry, "Iuliu Hațieganu" University of Medicine and Pharmacy, 41 Victor Babeș Street, 400012 Cluj-Napoca, Romania.
Antioxidants (Basel). 2025 May 26;14(6):636. doi: 10.3390/antiox14060636.
Oxidative stress represents a key process in many physiopathological mechanisms involved in several diseases. Therefore, antioxidants represent an important strategy in reversing this pathologic process. In the present study, we proposed the design, synthesis, computational, and in vitro evaluation of seven novel hydroxyphenyl-thiazole-coumarin hybrid compounds (-) as antioxidant molecules. The conducted theoretical quantum and thermodynamical calculations revealed compound as the most promising antioxidant, having the highest HOMO-LUMO gaps (3.13 eV in vacuum, 3.22 eV in nonpolar environment, and 3.33 in water) and some of the lowest BDE values (68.23 kcal/mol and 69.63 kcal/mol for O-H and N-H bonds in nonpolar environment). This was transposed in the results obtained following the in vitro antiradical (DPPH and ABTS) and electron transfer capacity assays (TAC, RP, FRAP, and CUPRAC), although all compounds showed important antioxidant activity, superior in almost all instances to ascorbic acid and Trolox, which were used as references. Compounds and can serve as molecules for further research involving in vivo antioxidant activity and possible synergistic mechanisms.
氧化应激是多种疾病所涉及的许多生理病理机制中的关键过程。因此，抗氧化剂是逆转这一病理过程的重要策略。在本研究中，我们提出了七种新型羟基苯基 - 噻唑 - 香豆素杂化化合物（-）作为抗氧化分子的设计、合成、计算和体外评估。进行的理论量子和热力学计算表明，化合物是最有前景的抗氧化剂，具有最高的HOMO - LUMO能隙（真空中为3.13 eV，非极性环境中为3.22 eV，水中为3.33）以及一些最低的BDE值（非极性环境中O - H和N - H键分别为68.23 kcal/mol和69.63 kcal/mol）。这在体外抗自由基（DPPH和ABTS）和电子转移能力测定（TAC、RP、FRAP和CUPRAC）的结果中得到体现，尽管所有化合物均表现出重要的抗氧化活性，在几乎所有情况下都优于用作参考的抗坏血酸和Trolox。化合物和可作为进一步研究体内抗氧化活性及可能协同机制的分子。
