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

Karaaslan C., Kadri H., ÇOBAN T., SÜZEN S., Westwell A. D.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, cilt.23, sa.9, ss.2671-2674, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 23 Sayı: 9
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.bmcl.2013.02.090
  • Dergi Adı: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2671-2674
  • Anahtar Kelimeler: Antioxidant, Indoles, Melatonin, ANTITUMOR BENZOTHIAZOLES, BIOLOGICAL-PROPERTIES, MELATONIN ANALOG, POTENT, INDOLE, 2-ARYLBENZOTHIAZOLE, DERIVATIVES, BEHAVIOR, RAT
  • Ankara Üniversitesi Adresli: Evet

Özet

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 1 mM concentration of 3b, respectively), at a level comparable with the reference standard MLT (98% and 75% at 1 mM). (C) 2013 Elsevier Ltd. All rights reserved.