新型基于螺环异吲哚酮的席夫碱的合成、抗氧化活性及构效关系研究。
Synthesis, antioxidant activity and SAR study of novel spiro-isatin-based Schiff bases.
机构信息
Pamukova Vocational High School, Sakarya University of Applied Sciences, 54900, Sakarya, Turkey.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Bezmialem Vakif University, 34093, Istanbul, Turkey.
出版信息
Mol Divers. 2019 Nov;23(4):829-844. doi: 10.1007/s11030-018-09910-7. Epub 2019 Jan 5.
A new series of 21 Schiff bases of spiro-isatin was synthesized, and their DPPH, CUPRAC and ABTS cation radical scavenging abilities were investigated for antioxidant activity. The results showed that all the synthesized compounds exhibited antioxidant activity for each assay. 5̍-(2,3-Dihydroxybenzylideneamino)spiro[[1,3] dioxolane-2,3̍-indoline]-2̍-on (5c) (IC = 4.49 µM, for DPPH; IC = 0.39 µM, for ABTS; and A = 0.42 µM, for CUPRAC) showed significantly better ABTS, CUPRAC and DPPH radical scavenging ability than quercetin (IC = 8.69 µM, for DPPH; IC = 15.49 µM, for ABTS; and A = 18.47 µM, for CUPRAC), which is used as a standard. SAR study showed that the synthesized compounds had higher ABTS activity than DPPH and CUPRAC activities. Moreover, the compounds (5c and 5d), containing two hydroxyl groups, exhibited the highest antioxidant activities for all assays. Quantum chemical calculations were also carried out to support SAR results.
合成了一系列 21 种新型螺环异吲哚啉席夫碱，并研究了它们对 DPPH、CUPRAC 和 ABTS 阳离子自由基清除能力的抗氧化活性。结果表明，所有合成的化合物在每种测定中都表现出抗氧化活性。5-（2,3-二羟基苯亚甲基氨基）螺[[1,3]二氧戊环-2,3-吲哚]-2-酮（5c）（IC = 4.49 µM，用于 DPPH；IC = 0.39 µM，用于 ABTS；A = 0.42 µM，用于 CUPRAC）在 ABTS、CUPRAC 和 DPPH 自由基清除能力方面明显优于用作标准的槲皮素（IC = 8.69 µM，用于 DPPH；IC = 15.49 µM，用于 ABTS；A = 18.47 µM，用于 CUPRAC）。SAR 研究表明，合成的化合物具有比 DPPH 和 CUPRAC 更高的 ABTS 活性。此外，含有两个羟基的化合物（5c 和 5d）在所有测定中表现出最高的抗氧化活性。还进行了量子化学计算以支持 SAR 结果。
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