Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara University, 06100 Tandogan, Ankara, Turkey.
Bioorg Med Chem Lett. 2013 May 1;23(9):2671-4. doi: 10.1016/j.bmcl.2013.02.090. Epub 2013 Mar 1.
In this study, we report the design, synthesis and antioxidant activity of a series of substituted 2-(4-aminophenyl)-1H-indoles and 2-(methoxyphenyl)-1H-indoles. The new compounds are structurally related to the known indole-based antioxidant lead compound melatonin (MLT), and the antitumour 2-(4-aminophenyl)benzothiazole and 2-(3,4-dimethoxyphenyl)benzothiazole series. Efficient access to the target 2-phenylindoles was achieved via Fischer indole synthesis between substituted phenylhydrazines and acetophenones. 2-(4-Aminophenyl)indoles (such as the 6-fluoro analogue 3b) in particular showed potent antioxidant activity in the DPPH and superoxide radical scavenging assays (80% and 81% inhibition at 1mM concentration of 3b, respectively), at a level comparable with the reference standard MLT (98% and 75% at 1 mM).
在这项研究中，我们报告了一系列取代的 2-(4-氨基苯基)-1H-吲哚和 2-(甲氧基苯基)-1H-吲哚的设计、合成和抗氧化活性。这些新化合物与已知的基于吲哚的抗氧化先导化合物褪黑素（MLT）以及抗肿瘤的 2-(4-氨基苯基)苯并噻唑和 2-(3,4-二甲氧基苯基)苯并噻唑系列在结构上有关联。通过取代的苯肼和苯乙酮之间的费歇尔吲哚合成，高效地获得了目标 2-苯基吲哚。特别是 2-(4-氨基苯基)吲哚（如 6-氟类似物 3b）在 DPPH 和超氧自由基清除测定中表现出很强的抗氧化活性（在 1mM 浓度下，分别为 80%和 81%的抑制率），与参考标准 MLT（在 1mM 时分别为 98%和 75%）相当。
