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Synthesis and Evaluation of Biological Activity of Homodrimane Sesquiterpenoids Bearing Hydrazinecarbothioamide or 1,2,4-Triazole Unit

Chemistry of Heterocyclic Compounds volume 55, pages 716–724 (2019)Cite this article

Synthesis of novel (+)-sclareolide-based homodrimane sesquiterpenoids bearing hydrazinecarbothioamide or N-substituted 1,2,4-triazole unit has been reported. These heterocyclic compounds demonstrate promising in vitro antifungal and antibacterial activities toward fungal species Aspergillus niger, Fusarium solani, Penicillium chrysogenum, Penicillium frequentans, and Alternaria alternata and bacteria strains Bacillus sp. and Pseudomonas aeruginosa at minimum inhibitory concentration level of μg/ml. In addition, two homodrimane sesquiterpenoids with hydrazinecarbothioamide fragment show cytotoxicity toward human ovarian carcinoma cells A2780 and A2780cis with half maximal inhibitory concentration values in range of 9–15 μM.

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Authors and Affiliations

  1. Institute of Chemistry, Laboratory “Chemistry of Natural and Biologically Active Compounds”, 3 Academiei St., MD-2028, Chisinau, Moldova

    Lidia Lungu, Alexandru Ciocarlan, Alic Barba, Sergiu Shova, Serghei Pogrebnoi & Aculina Aricu

  2. ”P. Poni” Institute of Macromolecular Chemistry, 41A Aleea Grigore Ghica Voda, RO-700487, Iasi, Romania

    Sergiu Shova

  3. ”Al. I. Cuza” University of Iasi, Faculty of Chemistry, 11 Carol Bd., RO-700506, Iasi, Romania

    Ionel Mangalagiu & Costel Moldoveanu

  4. Metropolitan Center of Research T.A.B.O.R., 9 Closca St., RO-700066, Iasi, Romania

    Nicoleta Vornicu

  5. University of Trento, Laboratory of Bioorganic Chemistry, 14 Via Sommarive, 38123, Trento, Italy

    Michele D’Ambrosio

  6. National University of Singapore, Department of Chemistry, 3 Science Drive 2, Singapore, 117543, Singapore

    Maria V. Babak

  7. University of Vienna, Institute of Inorganic Chemistry, 42 Währinger Straße, 1090, Vienna, Austria

    Vladimir B. Arion

Authors
  1. Lidia Lungu
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  2. Alexandru Ciocarlan
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  3. Alic Barba
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  4. Sergiu Shova
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  5. Serghei Pogrebnoi
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  6. Ionel Mangalagiu
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  7. Costel Moldoveanu
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  8. Nicoleta Vornicu
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  9. Michele D’Ambrosio
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  10. Maria V. Babak
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  11. Vladimir B. Arion
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  12. Aculina Aricu
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Corresponding author

Correspondence to Michele D’Ambrosio.

Additional information

Supplementary information file containing 1H and 13C NMR spectra of compounds 6, 7a–d, 8a–d, and 9a–d, HRMS of compounds 7c and 8d, and single crystal X-ray crystallographic data of compounds 8c and 9d is available at the journal website http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 716–724

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Lungu, L., Ciocarlan, A., Barba, A. et al. Synthesis and Evaluation of Biological Activity of Homodrimane Sesquiterpenoids Bearing Hydrazinecarbothioamide or 1,2,4-Triazole Unit. Chem Heterocycl Comp 55, 716–724 (2019). https://doi.org/10.1007/s10593-019-02526-1

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  • DOI: https://doi.org/10.1007/s10593-019-02526-1

Keywords

  • homodrimane sesquiterpenoid
  • hydrazinecarbothioamide
  • 1,2,4-triazole
  • antibacterial activity
  • anticancer activity
  • antifungal activity
  • microwave irradiation