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

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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.

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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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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran

    Khodabakhsh Niknam, Masoumeh Bavadi & Sanaz Mojikhalifeh

  2. Department of Medicinal Chemistry, Faculty of Pharmacy, Zahedan University of Medical Sciences, Zahedan, Iran

    Omolbanin Shahraki

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  1. Khodabakhsh Niknam
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  2. Masoumeh Bavadi
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  3. Sanaz Mojikhalifeh
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  4. Omolbanin Shahraki
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Correspondence to Khodabakhsh Niknam.

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Niknam, K., Bavadi, M., Mojikhalifeh, S. et al. A clean synthesis of 2,5-dihydro-1H-pyrrole-2-carboxylates under catalyst-free and solvent-free conditions: cytotoxicity and molecular docking studies. J IRAN CHEM SOC 15, 1613–1623 (2018). https://doi.org/10.1007/s13738-018-1359-2

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  • DOI: https://doi.org/10.1007/s13738-018-1359-2

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