Mojarrab Mahdi, Soltani Roozbeh, Aliabadi Alireza
Department of Pharmacognosy and Pharmaceutical Biotechnology, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, IR Iran.
Students Research Committee, Kermanshah University of Medical Sciences, Kermanshah, IR Iran ; Department of Medicinal Chemistry, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, IR Iran.
Jundishapur J Nat Pharm Prod. 2013 Aug;8(3):125-30. doi: 10.17795/jjnpp-10024. Epub 2013 Jul 17.
Natural chalcones and also their synthetic derivatives have attracted increasing attention due to various pharmacological applications. Development and discovery of new chalcones with antioxidant activities is one of the attracting areas in medicinal and natural product chemistry.
In the present study, a new series of pyridine based chalcones was synthesized and their antioxidant capacity was evaluated by beta carotene bleaching (BCB), DPPH free radical scavenging, ferrous ion chelating (FIC) activity and Trolox equivalent antioxidant capacity (TEAC) methods.
All compounds were synthesized via an aldol condensation procedure in methanol or ethanol solvent at room temperature and characterization was carried out by (1)HNMR, IR and MS spectroscopic methods. Related melting points were also measured for each compound.
Fortunately, compounds 3e (16.53 ± 1.21 µg/mL), 3g (58.85 ± 1.10 µg/mL) and 3i (58.73 ± 12.94 µg/mL) showed higher antioxidant activity (EC50 ± SD) in comparison with quercetin (87.24 ± 3.93 µg/mL) as reference agent in ferrous ion chelating method. Furthermore, compounds 3g (4.82 ± 0.11 µg/mL) and 3h (6.33 ± 0.30 µg/mL) also exhibited an acceptable antioxidant property compared to Trolox (3.83 ± 0.22 µg/mL) in TEAC method. None of synthesized compounds demonstrated significant antioxidant activity in DPPH free radical scavenging as well as beta carotene bleaching tests.
According to the obtained data, synthesized pyridine based chalcones (3a-3j) could be proposed as potential antioxidant lead compounds.
天然查尔酮及其合成衍生物因其多种药理应用而受到越来越多的关注。开发和发现具有抗氧化活性的新型查尔酮是药物化学和天然产物化学中引人关注的领域之一。
在本研究中，合成了一系列新型吡啶基查尔酮，并通过β-胡萝卜素漂白法（BCB）、DPPH自由基清除法、亚铁离子螯合（FIC）活性法和Trolox等效抗氧化能力（TEAC）法评估了它们的抗氧化能力。
所有化合物均在甲醇或乙醇溶剂中于室温下通过羟醛缩合反应合成，并通过（1）HNMR、IR和MS光谱方法进行表征。还测量了每种化合物的相关熔点。
幸运的是，在亚铁离子螯合法中，与作为参考剂的槲皮素（87.24±3.93μg/mL）相比，化合物3e（16.53±1.21μg/mL）、3g（58.85±1.10μg/mL）和3i（58.73±12.94μg/mL）表现出更高的抗氧化活性（EC50±SD）。此外，在TEAC法中，与Trolox（3.83±0.22μg/mL）相比，化合物3g（4.82±0.11μg/mL）和3h（6.33±0.30μg/mL）也表现出可接受的抗氧化性能。在DPPH自由基清除试验以及β-胡萝卜素漂白试验中，所合成的化合物均未表现出显著的抗氧化活性。
根据所得数据，所合成的吡啶基查尔酮（3a - 3j）可被提议作为潜在的抗氧化先导化合物。
