Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2018;27(9):2051-2061.
doi: 10.1007/s00044-018-2213-x. Epub 2018 Jul 17.

Novel triazoles of 3-acetylbetulin and betulone as anticancer agents

Ewa Bębenek  1 , Monika Kadela-Tomanek  1 , Elwira Chrobak  1 , Małgorzata Latocha  2 , Stanisław Boryczka  1
Affiliations
Review

Novel triazoles of 3-acetylbetulin and betulone as anticancer agents

Ewa Bębenek et al. Med Chem Res. 2018.

Abstract

The CuAAC reaction of azides and acetylenic triterpenes was used for synthesis of new triazoles of 3-acetylbetulin and betulone. The triazole derivatives were evaluated for their anticancer activity in vitro against amelanotic melanoma C-32, ductal carcinoma T47D and glioblastoma SNB-19 cell lines. 28-[1-(3'-Deoxythymidine-5'-yl)-1H-1,2,3-triazol-4-yl]carbonylbetulone 6e exhibited a significant IC50 value (0.17 µM) against the human glioblastoma SNB-19 cell line, an almost 5-fold higher potency while compared with reference cisplatin.

Keywords: 1,2,3-Triazole; Anticancer activity; Betulin; CuAAC; Lipophilicity.

PubMed Disclaimer

Conflict of interest statement

Compliance with ethical standardsThe authors declare that they have no conflict of interest.

Figures

Fig. 1
Fig. 1
Chemical structure of betulin 1 and 3-acetylbetulin 2
Scheme 1
Scheme 1
Synthesis of triazole derivatives 5a-i and 6a-j. Reagents and conditions: organic azide (RN3), CuI, reflux, 72 h
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Andri F, Héberger K. Towards better understanding of lipophilicity: assessment of in silico and chromatographic log P measures for pharmaceutically important compounds by nonparametric rankings. J Pharm Biomed Anal. 2015;115:183–191. doi: 10.1016/j.jpba.2015.07.006. - DOI - PubMed
    1. Bębenek E, Jastrzębska M, Kadela-Tomanek M, Chrobak E, Orzechowska B, Zwolińska K, Latocha M, Mertas A, Czuba Z, Boryczka S. Novel triazole hybrids of betulin: synthesis and biological activity profile. Molecules. 2017;22:1876–1892. doi: 10.3390/molecules22111876. - DOI - PMC - PubMed
    1. Bębenek E, Kadela-Tomanek M, Chrobak E, Wietrzyk J, Sadowska J, Boryczka New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity. Med Chem Res. 2016;26:1–8. doi: 10.1007/s00044-016-1713-9. - DOI - PMC - PubMed
    1. Bonacorso HG, Moraes MC, Wiethan CW, Luz FM, Meyer AR, Zanatta N, Martins MAP. Synthesis of 1H-1,2,3-triazoles-Rufinamide analogs by 1,3-dipolar cycloaddition and eletrocyclization reactions of trifluoroacetyl enolethers under thermal solventless conditions. J Flu Chem. 2013;156:112–119. doi: 10.1016/j.jfluchem.2013.09.005. - DOI
    1. Boryczka S, Bębenek E, Wietrzyk J, Kempińska K, Jastrzębska M, Kusz J, Nowak M. Synthesis, structure and cytotoxic activity of new acetylenic derivatives of betulin. Molecules. 2013;18:4526–4543. doi: 10.3390/molecules18044526. - DOI - PMC - PubMed

LinkOut - more resources