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

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Chemistry of Heterocyclic Compounds Aims and scope

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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References

  1. Jansen, B. J. M.; de Groot, Ae. Nat. Prod. Rep. 2004, 21, 449.

  2. (a) Kubo, I. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995, Vol. 17, p. 233. (b) Taniguchi, M.; Yano, Y.; Motoba, K.; Tanaka, T.; Oi, S.; Haraguchi, H.; Hashimoto, K.; Kubo, I. Agric. Biol. Chem. 1988, 52, 1881.

  3. Fritz, G. L.; Mills, G. D., Jr.; Warthen, J. D., Jr.; Waters, R. M. J. Chem. Ecol. 1989, 15, 2607.

    Article  CAS  PubMed  Google Scholar 

  4. Barrero, A. F.; Manzaneda, E. A.; Altarejos, J.; Salido, S.; Ramos, J. M.; Simmonds, M. S. J.; Blaney, W. M. Tetrahedron 1995, 51, 7435.

    Article  CAS  Google Scholar 

  5. Ciocarlan, A.; Aricu, A.; Lungu, L.; Edu, C.; Barba, A.; Shova, S.; Mangalagiu, I. I.; D'Ambrosio, M.; Nicolescu, A.; Deleanu, C.; Vornicu, N. Synlett 2017, 565.

  6. Viegas, C., Jr.; Danuello, A.; da Silva Bolzani, V.; Barreiro, E. J.; Fraga, C. A. M. Curr. Med. Chem. 2007, 14, 1829.

    Article  Google Scholar 

  7. Kuchkova, K.; Aricu, A.; Barba, A.; Vlad, P.; Shova, S.; Secara, E.; Ungur, N.; Zbancioc, Gh.; Mangalagiu, I. I. Synlett 2013, 697.

  8. Kuchkova, K.; Aricu, A.; Secara, E.; Barba, A.; Vlad, P.; Ungur, N.; Tuchilus, C.; Shova, S.; Zbancioc, Gh.; Mangalagiu, I. I. Med. Chem. Res. 2014, 23, 1559.

    Article  CAS  Google Scholar 

  9. (a) Kharb, R.; Sharma, P. C.; Yar, M. S. J. Enzyme Inhib. Med. Chem. 2011, 26, 1. (b) Gupta, D.; Jain, D. K. J. Adv. Pharm. Technol. Res. 2015, 6, 141. (c) Shen, Q.-K.; Liu, C.-F.; Zhang, H.-J.; Tian, Y.-S.; Quan, Z.-S. Bioorg. Med. Chem. Lett. 2017, 27, 4871. (d) Silva-Ortiz, A. V.; Bratoeff, E.; Ramírez-Apan, T.; Heuze, Y.; Sánchez, A.; Soriano, J.; Cabeza, M. Bioorg. Med. Chem. 2015, 23, 7535.

  10. Kuchkova, K. I.; Aricu, A. N.; Sekara, E. S.; Barba, A. N.; Vlad, P. F.; Makaev, F. Z.; Melnic, E.; Kravtsov, V. Kh. Chem. Nat. Compd. 2015, 51, 684. [Khim. Prir. Soedin. 2015, 589.]

  11. Cucicova, C.; Rudic, V.; Aricu, A.; Cepoi, L.; Rudi, L.; Secara, E.; Valuta, A.; Barba, A.; Miscu, V.; Vlad, P.; Chiriac, T. MD Patent 4327.

  12. Styngach, E. P.; Malinovskii, S. T.; Bets, L. P.; Vlad, L. A.; Gdanets, M.; Makaev, F. Z. J. Struct. Chem. 2005, 46, 765. [Zh. Struktur. Khim. 2005, 46, 785.]

  13. Namratha, B.; Gaonkar, S. L. Int. J. Pharm. Pharm. Sci. 2014, 6, 73.

    CAS  Google Scholar 

  14. Macaev, F.; Rusu, G.; Pogrebnoi, S.; Gudima, A.; Stingaci, E.; Vlad, L.; Shvets, N.; Kandemirli, F.; Dimoglo, A.; Reynolds, R. Bioorg. Med. Chem. 2005, 13, 4842.

    Article  CAS  PubMed  Google Scholar 

  15. Jogdand, G. F. Ph. D. Thesis, University of Pune: Pune, 2016.

  16. (a) Antimicrobial Susceptibility Testing (AST) Standards M07 and M100; National Committee on Clinical Laboratory Standards (NCCLS), 2003. (b) Cavalieri, S. J.; Harbeck, R. J.; McCarter, Y. S.; Ortez, J. H.; Rankin, I. D.; Sautter, R. L.; Sharp, S. E.; Spiegel, C. A. Manual of Antimicrobial Susceptibility Testing; Coyle, M. B., Ed.; American Society for Microbiology: Washington, 2005. (c) Arendrup, M. C.; Verweij, P.; Nielsen, H. V. Antimicrob. Agents Chemother. 2017, 61, e01659-16. (d) Thompson, G. R., III; Fothergill, A. W.; Wiederhold, N. P.; Vallor, A. C.; Wickes, B. L.; Patterson, T. F. Antimicrob. Agents Chemother. 2008, 52, 2959. (e) Espinel-Ingroff, A.; Rezusta, A. J. Clin. Microbiol. 2002, 40, 2101.

  17. CrysAlis RED, v1.171.34.76; Oxford Diffraction Ltd.: Abingdon, 2003.

  18. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

  19. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

  20. Sîrbu, A.; Palamarciuc, O.; Babak, M. V.; Lim, J. M.; Ohui, K.; Enyedy, E. A.; Shova, S.; Darvasiová, D.; Rapta, P.; Ang, W. H.; Arion, V. B. Dalton Trans. 2017, 46, 3833.

    Article  CAS  PubMed  Google Scholar 

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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

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