A clean synthesis of 2,5-dihydro-1H-pyrrole-2-carboxylates under catalyst-free and solvent-free conditions: cytotoxicity and molecular docking studies

  • Khodabakhsh Niknam
  • Masoumeh Bavadi
  • Sanaz Mojikhalifeh
  • Omolbanin Shahraki
Original Paper
  • 12 Downloads

Abstract

A concise, clean synthetic approach to access of 2,5-dihydro-1H-pyrrole-2-carboxylates by two-component condensation reaction of ethyl pyruvate and aniline derivatives under catalyst-free and solvent-free conditions is described. The advantages of this method are practical simplicity, catalyst-free and solvent-free conditions, high atom economy, short reaction times, and good yields of the products. The anticancer potential of synthesized compounds was evaluated against MCF7, MOLT-4 and HL-60 cells by using MTT assay. Among the tested synthesized 2,5-dihydro-1H-pyrrole-2-carboxylates (3a-h, 4a-d), compound 4d having sulfonamide moiety exhibited good cytotoxic activity against all tested cell lines and molecular docking studies also demonstrated that the results of the docking study are in reasonable agreement with cytotoxicity activities.

Graphical Abstract

A series of 2,5-dihydro-1H-pyrrole-2-carboxylate derivatives were synthesized by two-component condensation reaction of ethyl pyruvate and aniline derivatives under catalyst-free and solvent-free conditions.

Keywords

Clean synthesis 2,5-Dihydro-1H-pyrrole-2-carboxylates Ethyl pyruvate Catalyst-free Two-component reactions Cytotoxicity Molecular docking 

Notes

Acknowledgements

We are thankful to Persian Gulf University Research Council for partial support of this work. Also, we are thankful to the School of Chemistry, Manchester University, for running NMRs.

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Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Khodabakhsh Niknam
    • 1
  • Masoumeh Bavadi
    • 1
  • Sanaz Mojikhalifeh
    • 1
  • Omolbanin Shahraki
    • 2
  1. 1.Department of Chemistry, Faculty of SciencesPersian Gulf UniversityBushehrIran
  2. 2.Department of Medicinal Chemistry, Faculty of PharmacyZahedan University of Medical SciencesZahedanIran

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