Abstract
BackgroundThe main aim of this work was to synthesise a novel N-(substituted phenyl)-2-(3-(hydroxyimino) methyl)-1H-indol-1-yl) acetamide derivatives and evaluate their antioxidant activity. These compounds were prepared by a condensation reaction between 1H-indole carbaldehyde oxime and 2-chloro acetamide derivatives. The newly synthesised compound structures were characterised by FT-IR, 1H-NMR, mass spectroscopy and elemental analysis. Furthermore, the above-mentioned compounds were screened for antioxidant activity by using ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) methods.ResultThe antioxidant activity result reveals that most of the compounds were exhibiting considerable activity in both methods and the values are very closer to the standards. Among the synthesised compounds, compound 3j, 3a and 3k were shown remarkable activity at low concentration.ConclusionCompounds 3j, 3a and 3k were shown highest activity among the prepared analogues due to the attachment of halogens connected at the appropriate place in the phenyl ring. Hence, these substituted phenyl rings considered as a perfect side chain for the indole nucleus for the development of the new antioxidant agents.
Highlights
The main aim of this work was to synthesise a novel N-(substituted phenyl)-2-(3-(hydroxyimino) methyl)-1H-indol-1-yl) acetamide derivatives and evaluate their antioxidant activity
Functional groups present in the compounds were confirmed by using IR spectra (KBr) were recorded on a Shimadzu Fourier transform infrared spectroscopy (FT-IR) 8400S spectrophotometer between the ranges from 4000 cm−1 to 400 cm−1. Nuclear magnetic resonance spectroscopy (1H-NMR) spectra were determined on a Bruker NMR spectrometer (500 MHz). 13C-NMR spectra were performed on a Bruker NMR spectrometer (100 MHz) and fully decoupled
[1] An equimolar mixture of indole (0.001 mol), N, N-dimethyl formamide (0.001 mol) and 8.75 ml of phosphorous oxychloride was poured into the round bottom
Summary
The main aim of this work was to synthesise a novel N-(substituted phenyl)-2-(3-(hydroxyimino) methyl)-1H-indol-1-yl) acetamide derivatives and evaluate their antioxidant activity. These compounds were prepared by a condensation reaction between 1H-indole carbaldehyde oxime and 2-chloro acetamide derivatives. In 1986, Adolf von Bayer prepared indole from oxindole by a simple chemical reaction using zinc dust [3] Indole and their derivatives are identified as a non-basic nitrogenous pharmacophore exhibiting a broad range of useful biological activities such as anti-inflammatory [4], anti-depressant [5], antifungal [6], anti-cancer [7], antihypertensive [8], antibiotic [9], anti-microbial agent [10], anti-viral [11], chelating agents [12], antimalarial [13], anti-HIV [14], anti-. N-(substituted phenyl)-2-(3-(hydroxyimino) methyl)-1Hindol-1-yl) acetamide derivatives were synthesised and evaluated their antioxidant activity by using ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2picrylhydrazyl (DPPH) method.
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