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New Synthetic Method and Antioxidant Activity of Betulin Diformate and Allobetulin Formate

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Chemistry of Natural Compounds Aims and scope

A simple and effective method for formylation of betulin using formic acid and 3a,6a-diphenylthioglycoluril is reported. The yield of betulin diformate was 87%. Allobetulin formate (95%) was prepared by reacting betulin diformate with trifluoroacetic acid. The structures of betulin diformate and allobetulin formate were confirmed by IR and NMR spectroscopy. The antioxidant activity of the synthesized compounds was studied.

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References

  1. D. W. C. MacMillan, Nature (London), 455, 304 (2008).

    Article  CAS  Google Scholar 

  2. A. G. Doyle and E. N. Jacobsen, Chem. Rev., 107, 5713 (2007).

    Article  CAS  Google Scholar 

  3. (a) Y. Takemoto, Org. Biomol. Chem., 3, 4299 (2005); (b) P. M. Pihko, Angew. Chem., Int. Ed., 43, 2062 (2004); (c) M. S. Taylor and E. N. Jacobsen, Angew. Chem., Int. Ed., 45, 1520 (2006); (d) A. G. Doyle and E. N. Jacobsen, Chem. Rev., 107, 5713 (2007).

  4. C. J. Broan, A. R. Butler, D. Reed, and I. H. Sadler, J. Chem. Soc., Perkin Trans. 2, 731 (1989).

    Article  Google Scholar 

  5. L. Cao, J. Ding, G. Yin, M. Gao, M. Li, and A. Wu, Synlett, 9, 1445 (2009).

    Google Scholar 

  6. S. Khaksar, S. M. Vahdat, M. Tajbakhsh, F. Jahani, and A. Heydari, Tetrahedron Lett., 51 (49), 6388 (2010).

    Article  CAS  Google Scholar 

  7. T. R. Shesadri and T. N. C. Vedanthan, Phytochemistry, 10, 897 (1971).

    Article  Google Scholar 

  8. A. K. Batta and S. Rangaswami, Phytochemistry, 12, 214 (1973).

    Article  CAS  Google Scholar 

  9. C. A. Dehelean, S. C. Pinzaru, C. I. Peev, C. Soica, and D. S. Antal, J. Optoelectron. Adv. Mater., 9, 783 (2007).

    Google Scholar 

  10. E. E. Kovac-Besovic, K. Duric, Z. Kalodera, and E. Sofic, Bosnian J. Basic Med. Sci., 9, 31 (2009).

    Article  Google Scholar 

  11. (a) T. R. Shesadri and T. N. C. Vedanthan, Phytochemistry, 10, 897 (1971); (b) B. Green, M. D. Bentley, B. Y. Chung, N. G. Lynch, and B. L. Jensen, J. Chem. Educ., 84, 1985 (2007); (c) T.-S. Li, J.-X. Wang, and X.-J. Zheng, J. Chem. Soc., Perkin Trans. 1, 3957 (1998).

  12. H. Schulze and K. Pieroh, “Zur Kenntnis des Betulins,” Chem. Ber., 55, 2332 (1922).

    Article  Google Scholar 

  13. F. N. Lugemwa, F. Y. Huang, M. D. Bentley, M. J. Mendel, and A. R. A. Alford, J. Agric. Food Chem., 38, 493 (1990).

    Article  CAS  Google Scholar 

  14. S. G. Errington, E. L. Ghisalberti, and P. R. Jefferies, Aust. J. Chem., 29, 1809 (1976).

    Article  CAS  Google Scholar 

  15. E. Plotnikov, O. Voronova, W. Linert, D. Martemianov, E. Korotkova, E. Dorozhko, A. Astashkina, I. Martemianova, S. Ivanova, and N. Bokhan, J. App. Pharm. Sci., 6 (1), 086 (2016).

    Article  CAS  Google Scholar 

  16. E. Plotnikov, E. Korotkova, O. Voronova, N. Sazhina, E. Petrova, A. Artamonov, L. Chernyavskaya, and E. Dorozhko, Arch. Med. Sci., 12 (5), 1071 (2016).

    Article  Google Scholar 

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Acknowledgment

The work was sponsored by the Ministry of Education and Science of the Russian Federation (Grant No. 05-13108). Antioxidant activity was studied in the framework of state task “Nauka” No. 4.5752.2017 and a program for increasing the competency of Tomsk Polytechnic University.

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Correspondence to Salah Arrous.

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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November−December, 2019, pp. 941−944.

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Arrous, S., Boudebouz, I., Parunov, I. et al. New Synthetic Method and Antioxidant Activity of Betulin Diformate and Allobetulin Formate. Chem Nat Compd 55, 1094–1097 (2019). https://doi.org/10.1007/s10600-019-02902-5

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  • DOI: https://doi.org/10.1007/s10600-019-02902-5

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