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Synthesis, spectroscopic, in vitro cytotoxicity and crystal structures of novel fluorinated dispiroheterocycles: DFT approach

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Abstract

The reaction of azomethine ylide generated in situ from ninhydrin and sarcosine/thiaproline with fluorinated cyclopent[b]indole dipolarophiles in refluxing dioxane and methanol afforded a novel class of fluorinated cyclopent[b]indole dispiroheterocycles via 1,3-dipolar cycloaddition. The crystal structures of 4′-[4-(trifluoromethyl)phenyl]-1′,5-dimethyl-2,3-dihydrodispiro[cyclopent[b]-indol-2,3′-pyrrolidine-2′,2″-indene]-1,1″,3″-trione and 4′-(4-fluorophenyl)-5-methyl-2,3-dihydrodispiro[cyclopent[b]indol-2,3′-pyrrolizidine-2′,2″-indene]-1,1″,3″-trione are reported. New compounds are investigated theoretically via DFT calculations utilizing M062X hybrid function with 6-311++G(d,p) basis sets in vacuum. Results from in vitro cytotoxicity screening are compared with those of standard drugs.

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Acknowledgements

Rajendran Satheeshkumar is grateful to the University Grant Commission (UGC-SAP), New Delhi, for BSR—Senior Research Fellowship, which is thankfully acknowledged. Dr. Karnam Jayarampillai Rajendra Prasad greatly acknowledged UGC-Emeritus fellowship for research. Dr. Werner Kaminsky thanks the Department of Chemistry, University of Washington, Seattle, USA, for access to the X-ray diffraction facility. Dr. Koray Sayin thanks to the High Performance and Grid Computing Center (TRUBA Resources), numerical calculations are performed at TUBITAK ULAKBIM.

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Authors and Affiliations

  1. Department of Chemistry, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India

    Rajendran Satheeshkumar & Karnam Jayarampillai Rajendra Prasad

  2. Department of Chemistry, Institute of Science, Cumhuriyet University, 58140, Sivas, Turkey

    Koray Sayin

  3. Department of Chemistry, University of Washington, Seattle, WA, 98195, USA

    Werner Kaminsky

Authors
  1. Rajendran Satheeshkumar
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  2. Koray Sayin
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  3. Werner Kaminsky
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  4. Karnam Jayarampillai Rajendra Prasad
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Corresponding author

Correspondence to Karnam Jayarampillai Rajendra Prasad.

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Satheeshkumar, R., Sayin, K., Kaminsky, W. et al. Synthesis, spectroscopic, in vitro cytotoxicity and crystal structures of novel fluorinated dispiroheterocycles: DFT approach. Monatsh Chem 149, 141–147 (2018). https://doi.org/10.1007/s00706-017-2050-5

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  • DOI: https://doi.org/10.1007/s00706-017-2050-5

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