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

A hybrid pharmacophore approach for the synthesis of isomeric pyranoindolones was achieved by employing gold(III) chloride-catalyzed cycloisomerization of alkyne-tethered indole carboxylic acids in good to excellent yield. All the synthesized compounds were evaluated for their tumor cell growth inhi...

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Published inJournal of chemical sciences (Bangalore, India) Vol. 128; no. 5; pp. 787 - 802
Main Authors JEYAVEERAN, J C, PRAVEEN, CHANDRASEKAR, ARUN, Y, PRINCE, A A M, PERUMAL, P T
Format Journal Article
LanguageEnglish
Published New Delhi Springer India 01.05.2016
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
chemical synthesis
positional isomers
molecular docking
gold catalysis
Pyranoindolones
cytotoxicity
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Summary:A hybrid pharmacophore approach for the synthesis of isomeric pyranoindolones was achieved by employing gold(III) chloride-catalyzed cycloisomerization of alkyne-tethered indole carboxylic acids in good to excellent yield. All the synthesized compounds were evaluated for their tumor cell growth inhibitory activity against human cervix adenocarcinoma (HeLa) which revealed that three compounds exhibited activity comparable with the standard cis -platin (IC 50 = 0.08 μ M). 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 energy of binding as −8.27 kcal/mol. Graphical Abstract A highly regioselective synthesis of isomeric pyranoindolones through AuCl 3 catalyzed 6-endo-dig cycloisomerization of acetylene tethered indole carboxylic acids in moderate to good yield was achieved. In addition, all the synthesized compounds were evaluated for their cytotoxic potential against human cervix adenocarcinoma cells.
ISSN:0974-3626
0973-7103
DOI:10.1007/s12039-016-1070-8