Ullah Atta, Rohman Nur, Ardiansah Bayu, Cahyana Antonius Herry, Almehizia Abdulrahman A
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok 16424, Indonesia.
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.
MethodsX. 2023 Aug 7;11:102322. doi: 10.1016/j.mex.2023.102322. eCollection 2023 Dec.
The substituted 1,2,3-triazole core is prevalent in numerous commercially available drugs utilized for a wide range of clinical applications. Simultaneously, chalcone represents a privileged framework discovered in natural products exhibiting intriguing bioactivities. In this study, we synthesized triazole-bonded chalcone compounds (-), starting from a simple aromatic ketone, acetophenone, which underwent aldol condensation to give hydroxychalcone intermediate. In the second step, the hydroxyl group of chalcone compound was adducted with propargyl moiety through propargylation reaction. Then, the propargylated products underwent smooth copper-mediated azide-alkyne cyclization to give the triazole-bonded chalcones as the final products. They were characterized by IR, NMR and HRMS, and evaluated their radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH). Among the tested products, compound was denoted as the most potent derivative which can inhibit DPPH radical in 91.62 ± 0.10% at 500 ppm.•Acetophenone as a simple ketone was modified to triazole-bonded chalcones.•Modification was performed through three steps reaction.•Final products exhibited free radical scavenging activity.
取代的1,2,3 - 三唑核心在众多用于广泛临床应用的市售药物中普遍存在。同时，查尔酮是在具有有趣生物活性的天然产物中发现的一种特殊结构。在本研究中，我们从简单的芳香酮苯乙酮开始合成了三唑键合的查尔酮化合物（-），苯乙酮经过羟醛缩合得到羟基查尔酮中间体。第二步，查尔酮化合物的羟基通过炔丙基化反应与炔丙基部分加成。然后，炔丙基化产物顺利进行铜介导的叠氮化物 - 炔烃环化反应，得到三唑键合的查尔酮作为最终产物。通过红外光谱、核磁共振和高分辨质谱对它们进行了表征，并评估了它们对2,2 - 二苯基 - 1 - 苦基肼（DPPH）的自由基清除活性。在测试的产物中，化合物被认为是最有效的衍生物，在500 ppm时能以91.62±0.10%的比例抑制DPPH自由基。
•苯乙酮作为一种简单的酮被修饰为三唑键合的查尔酮。
•通过三步反应进行修饰。
•最终产物表现出自由基清除活性。
