• Chandrasekar Praveen

      Articles written in Journal of Chemical Sciences

    • Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles

      J C Jeyaveeran Chandrasekar Praveen Y Arun A A M Prince P T Perumal

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      The synthesis of substituted isoxazoles and pyrazoles through a general cycloisomerization methodology has been reported. The capability of gold(III) chloride to promote cycloisomerization of both 𝛼, 𝛽-acetylenic oximes and 𝛼, 𝛽-acetylenic hydrazones is the centrepiece of the strategy. A range of acetylenic precursors were investigated to afford 28 examples of the products with good to excellent chemical yields. Selected compounds were screened for their cytotoxic potential towards COLO320 cancer cell lines. The IC50 values of the tested compounds were in the micromolar range, with the best compound, 5-(6-Methoxy-naphthalen-2-yl)-3-phenyl-isoxazole (3h) displaying an IC50 of 38.9 𝜇M. For this compound, the crystal structure in complex with Aurora-A kinase was obtained which revealed details of its binding mode within the active site with a free energy of binding -9.54 kcal/mol.

    • Flexible synthesis of isomeric pyranoindolones and evaluation of cytotoxicity towards HeLa cells


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      A hybrid pharmacophore approach for the synthesis of isomeric pyranoindolones was achievedby employing gold(III) chloride-catalyzed cycloisomerization of alkyne-tethered indole carboxylic acids ingood to excellent yield. All the synthesized compounds were evaluated for their tumor cell growth inhibitoryactivity against human cervix adenocarcinoma (HeLa) which revealed that three compounds exhibited activitycomparable with the standard cis-platin $(IC_{50} = 0.μM)$. Molecular docking of all the compounds in Vaccinia H1-Related (VHR) Phosphatase receptor also supported that compound 7d as the most active with a free energyof binding as - 8.27 kcal/mol.

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