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Semi-synthesis, antibacterial and antifungal activities of three novel thiazolidin-4-one by essential oil of Anethum graveolens seeds as starting material

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Abstract

The three novel compounds of thiazolidin-4-one were synthesized by the reaction of essential oil of Anethum graveolens seeds (containing carvone) with thiosemicarbazide and acetylenic esters. The essential oil of A. graveolens seeds were analyzed by GC–MS after extraction that were containing high amount of carvone (37%). Carvonethiosemicarbazone was produced by the reaction of carvone with thiosemicarbazide that this compound in the reaction with acetylenic esters produced thiazolidin-4-one derivatives. The synthetic compounds 6a–c was confirmed by FT-IR, 1H-NMR, 13C-NMR and mass spectral data. Antimicrobial and antifungal activities of the synthetic compounds were assessed against 9 Gram-positive and 7 Gram-negative pathogenic bacteria as well as three fungal strains. The activities were reported as inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration and minimum fungicidal concentration values.

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Acknowledgements

We gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    Zahra Ahani, Mohammad Nikbin, Malek-Taher Maghsoodlou & Farhang Farhadi-Ghalati

  2. Department of Biology, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran

    Jafar Valizadeh

  3. Department of Chemistry, Faculty of Science, University of Zabol, Zabol, Iran

    Hamid Beyzaei

  4. Department of Chemistry, Kerman Branch, Islamic Azad University, Kerman, Iran

    Mohammadreza Moghaddam-Manesh

Authors
  1. Zahra Ahani
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  2. Mohammad Nikbin
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  3. Malek-Taher Maghsoodlou
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  4. Farhang Farhadi-Ghalati
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  5. Jafar Valizadeh
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  6. Hamid Beyzaei
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  7. Mohammadreza Moghaddam-Manesh
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Correspondence to Malek-Taher Maghsoodlou.

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Ahani, Z., Nikbin, M., Maghsoodlou, MT. et al. Semi-synthesis, antibacterial and antifungal activities of three novel thiazolidin-4-one by essential oil of Anethum graveolens seeds as starting material. J IRAN CHEM SOC 15, 2423–2430 (2018). https://doi.org/10.1007/s13738-018-1431-y

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  • DOI: https://doi.org/10.1007/s13738-018-1431-y

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