Design and synthesis of novel thiopheno-4-thiazolidinylindoles as potent antioxidant and antimicrobial agents
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Jaiprakash Biradar
,
Parveen Rajesab
Abstract
A novel and convenient synthesis of thiopheno-4-thiazolidinyl indole analogues is presented (IVa-IVi), with the aim of obtaining biologically active compounds. 3,5-disubstituted indol-2-carboxyhydrazides (Ia-If) were allowed to react with 3-acetyl-2,5-dichlorothiophene (II) to yield the corresponding 3,5-disubstituted indol-2-carbohydrazides (IIIa-IIIf). The pre-formed indolecarbohydrazides (IIIa-IIIf) were allowed to react with 2-mercaptoacetic acid or 2-mercaptopropanoic acid to produce thiopheno-4-thiazolidinylindoles (IVa-IVi). This reaction protocol affords a simple, eco-friendly, non-hazardous, easier preparation and high yields. The antioxidant (free radical scavenging, total antioxidant capacity and ferric-reducing antioxidant power) and antimicrobial activities of the synthesised compounds were evaluated. The structures and purity of the products were confirmed by their IR, 1H NMR, 13C NMR and mass spectral and analytical data. Most of the compounds tested showed very significant scavenging, antioxidant and antimicrobial activities. Compounds containing electron donor group (CH3) at the fifth position of indole exhibit an excellent ferric-reducing activity. The present study suggests that compounds IIIa-IIIb, IIIf, IVa-IVc, IVf-IVi, may serve as promising lead scaffolds for antioxidant and antimicrobial agents.
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© 2013 Institute of Chemistry, Slovak Academy of Sciences
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Artikel in diesem Heft
- Analytical protocol for investigation of zinc speciation in plant tissue
- Assessment of waxy and non-waxy corn and wheat cultivars as starch substrates for ethanol fermentation
- Effect of quaternary ammonium silane coating on adhesive immobilization of industrial yeasts
- Modeling of supercritical fluid extraction of flavonoids from Calycopteris floribunda leaves
- Determination of limiting current density for different electrodialysis modules
- Dyeing of multiple types of fabrics with a single reactive azo disperse dye
- Physicochemical fractionation of americium, thorium, and uranium in Chernozem soil after sharp temperature change and soil drought
- Ultra-trace determination of Pb(II) and Cd(II) in drinking water and alcoholic beverages using homogeneous liquid-liquid extraction followed by flame atomic absorption spectrometry
- Synthesis, thermal stability, electronic features, and antimicrobial activity of phenolic azo dyes and their Ni(II) and Cu(II) complexes
- Inhibition of copper corrosion in acidic sulphate media by eco-friendly amino acid compound
- Formation of nanostructured polyaniline by dopant-free oxidation of aniline in a water/isopropanol mixture
- Total synthesis of cannabisin F
- Design and synthesis of novel thiopheno-4-thiazolidinylindoles as potent antioxidant and antimicrobial agents
- Microwave-assisted synthesis and antibacterial activity of derivatives of 3-[1-(4-fluorobenzyl)-1H-indol-3-yl]-5-(4-fluorobenzylthio)-4H-1,2,4-triazol-4-amine
- DFT study on [4+2] and [2+2] cycloadditions to [60] fullerene
- Efficient thioacetalisation of carbonyl compounds
- Trimerization of aldehydes with one α-hydrogen catalyzed by sodium hydroxide
