Synthesis and antioxidant properties of substituted 2-phenyl-1H-indoles

Karaaslan, Cigdem, Kadri, Hachemi, Coban, Tulay, Suzen, Sibel and Westwell, Andrew D. (2013) Synthesis and antioxidant properties of substituted 2-phenyl-1H-indoles. Bioorganic & Medicinal Chemistry Letters, 23(9), pp. 2671-2674. ISSN (print) 0960-894X


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).

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