Synthesis, Biological Evaluation, and Molecular Docking Studies of Hexahydro-1H-xanthene-1,8(2H)-dione and 1,2,3-Triazole Hybrids as Potent Free Radical Scavengers

IF 1.7 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Russian Journal of Bioorganic Chemistry Pub Date : 2025-07-28 DOI:10.1134/S1068162024606013

Jaydeep N. Lalpara, Bhavin B. Dhaduk, G. G. Dubal, Maneesh Kumar Gupta, Chandan Kumar Pashavan, Jayendra Kanzariya, Rakesh Rola, Mayur Shiyal, Sanjay D. Hadiyal

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引用次数: 0

Abstract

Objective: To develop and synthesize new hybrid compounds incorporating hexahydro-1H-xanthene-1,8(2H)-dione and 1,2,3-triazole with potential free radical inhibitory activity. Methods: The structures of all synthesized compounds were confirmed by ¹H and ¹³C NMR spectroscopy, as well as by elemental analysis. A molecular docking study was conducted for the designed compounds against the 1PRX receptor. Furthermore, the antioxidant activity of all synthesized compounds was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydrogen peroxide (H₂O₂), and nitric oxide (NO) assays. Results and Discussion: A direct transformation of a xanthene-based intermediate into triazole hybrids via a Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction was developed, affording the desired products in 73–91% yields. Conclusions: Compound (VIIh) exhibited notable antioxidant potential compared to the reference standard.

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六氢- 1h -杂蒽-1,8(2H)-二酮和1,2,3-三唑强自由基清除剂的合成、生物学评价及分子对接研究

目的：开发合成具有潜在自由基抑制活性的六氢- 1h -杂蒽-1,8(2H)-二酮和1,2,3-三唑的杂化化合物。方法：通过 1H、 13C NMR及元素分析对合成的化合物结构进行确证。对设计的化合物与1PRX受体进行了分子对接研究。此外，利用2,2-二苯基-1-苦味酰肼（DPPH）、过氧化氢（H2O2）和一氧化氮（NO）测定了所有合成化合物的抗氧化活性。结果与讨论：通过Cu(I)催化叠氮-炔环加成（CuAAC）反应，建立了以杂蒽为基础的中间体直接转化为三唑杂化产物的反应，产率为73-91%。结论：与对照品相比，化合物（VIIh）具有显著的抗氧化活性。

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来源期刊

Russian Journal of Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

1.80

自引率

10.00%

发文量

118

审稿时长

3 months

期刊介绍： Russian Journal of Bioorganic Chemistry publishes reviews and original experimental and theoretical studies on the structure, function, structure–activity relationships, and synthesis of biopolymers, such as proteins, nucleic acids, polysaccharides, mixed biopolymers, and their complexes, and low-molecular-weight biologically active compounds (peptides, sugars, lipids, antibiotics, etc.). The journal also covers selected aspects of neuro- and immunochemistry, biotechnology, and ecology.