title: Synthesis and antioxidant properties of substituted 2-phenyl-1H-indoles.
abstract: 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).
authors.affiliation: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara University, 06100 Tandogan, Ankara, Turkey.
authors.forename: Cigdem
authors.initials: C
authors.lastname: Karaaslan
authors.forename: Hachemi
authors.initials: H
authors.lastname: Kadri
authors.forename: Tulay
authors.initials: T
authors.lastname: Coban
authors.forename: Sibel
authors.initials: S
authors.lastname: Suzen
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Westwell
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D052160:Benzothiazoles / Q000737:chemistry; D015195:Drug Design; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008550:Melatonin / Q000737:chemistry; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000737:chemistry / Q000378:metabolism
chemical_list: C111133:2-(4-aminophenyl)benzothiazole; D000970:Antineoplastic Agents; D000975:Antioxidants; D052160:Benzothiazoles; D007211:Indoles; D013481:Superoxides; D008550:Melatonin