Cu(OTf)2 catalyzed three component strategy for the synthesis of thienopyridine containing spirooxindoles and their cytotoxic evaluation

K. Parthasarathy; C. Praveen; P. Senthil Kumar; C. Balachandran; P. T. Perumal

doi:10.1039/c4ra16605a

Cu(OTf)₂ catalyzed three component strategy for the synthesis of thienopyridine containing spirooxindoles and their cytotoxic evaluation

K. Parthasarathy, C. Praveen, P. Senthil Kumar, C. Balachandran, P. T. Perumal

Research Institute for Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Synthesis of novel spirooxindoles via a three component reaction of thienopyridines, isatins and malononitriles under copper catalysis was accomplished. This one-pot, room temperature protocol allowed the synthesis of diversely substituted spirooxindoles in good to excellent yields. Cytotoxicity towards COLO320 cells revealed that compound 5v possessing a 2,6-difluorobenzyl group (IC₅₀ of 49.1 μM) was found to be highly potent among the screened compounds. In addition, molecular docking of compound 5v into caspase-3 receptors exhibited the largest binding energy (-10.5 kcal mol^-1) compared to other compounds. The formation of a DNA ladder for compound 5v also supports the experimental results.

Original language	English
Pages (from-to)	15818-15830
Number of pages	13
Journal	RSC Advances
Volume	5
Issue number	21
DOIs	https://doi.org/10.1039/c4ra16605a
Publication status	Published - 2015

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abstract = "Synthesis of novel spirooxindoles via a three component reaction of thienopyridines, isatins and malononitriles under copper catalysis was accomplished. This one-pot, room temperature protocol allowed the synthesis of diversely substituted spirooxindoles in good to excellent yields. Cytotoxicity towards COLO320 cells revealed that compound 5v possessing a 2,6-difluorobenzyl group (IC50 of 49.1 μM) was found to be highly potent among the screened compounds. In addition, molecular docking of compound 5v into caspase-3 receptors exhibited the largest binding energy (-10.5 kcal mol-1) compared to other compounds. The formation of a DNA ladder for compound 5v also supports the experimental results.",

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AU - Parthasarathy, K.

AU - Praveen, C.

AU - Kumar, P. Senthil

AU - Balachandran, C.

AU - Perumal, P. T.

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N2 - Synthesis of novel spirooxindoles via a three component reaction of thienopyridines, isatins and malononitriles under copper catalysis was accomplished. This one-pot, room temperature protocol allowed the synthesis of diversely substituted spirooxindoles in good to excellent yields. Cytotoxicity towards COLO320 cells revealed that compound 5v possessing a 2,6-difluorobenzyl group (IC50 of 49.1 μM) was found to be highly potent among the screened compounds. In addition, molecular docking of compound 5v into caspase-3 receptors exhibited the largest binding energy (-10.5 kcal mol-1) compared to other compounds. The formation of a DNA ladder for compound 5v also supports the experimental results.

AB - Synthesis of novel spirooxindoles via a three component reaction of thienopyridines, isatins and malononitriles under copper catalysis was accomplished. This one-pot, room temperature protocol allowed the synthesis of diversely substituted spirooxindoles in good to excellent yields. Cytotoxicity towards COLO320 cells revealed that compound 5v possessing a 2,6-difluorobenzyl group (IC50 of 49.1 μM) was found to be highly potent among the screened compounds. In addition, molecular docking of compound 5v into caspase-3 receptors exhibited the largest binding energy (-10.5 kcal mol-1) compared to other compounds. The formation of a DNA ladder for compound 5v also supports the experimental results.

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Cu(OTf)₂ catalyzed three component strategy for the synthesis of thienopyridine containing spirooxindoles and their cytotoxic evaluation

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