Novel Triazole Hybrids of Betulin: Synthesis and Biological Activity Profile

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Ewa BębenekStanisław Boryczka

Abstract

Betulin derivatives containing a 1,2,3-triazole ring possess a wide spectrum of biological activities, including antiviral, anticancer, and antibacterial activity. A series of novel triazoles were prepared by the 1,3-dipolar cycloaddition reaction between the alkyne derivatives of betulin and organic azides. The chemical structures of the obtained compounds were defined by ¹H and 13C NMR, IR, and high-resolution mass spectrometry (HR-MS) analysis. The target triazoles were screened for their antiviral activity against DNA and RNA viruses. The cytotoxic activity of the obtained compounds 5a-k and 6a-h was determined using five human cancer cell lines (T47D, MCF-7, SNB-19, Colo-829, and C-32) by a WST-1 assay. The bistriazole 6b displayed a promising IC50 value (0.05 μM) against the human ductal carcinoma T47D (500-fold higher potency than cisplatin). The microdilution method was applied for an evaluation of the antimicrobial activity of all of the compounds. The triazole 5e containing a 3'-deoxythymidine-5'-yl moiety exhibited antibacterial activity against two gram-negative bacteria vz. Klebsiellapneumoniae and Escherichia coli (minimal inhibitory concentration (MIC) range of 0.95-1.95 μM).

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Citations

Sep 18, 2018·Medicinal Chemistry Research : an International Journal for Rapid Communications on Design and Mechanisms of Action of Biologically Active Agents·Ewa BębenekStanisław Boryczka
Mar 22, 2019·International Journal of Molecular Sciences·Ewa BębenekStanisław Boryczka
Apr 5, 2019·Journal of Analytical Methods in Chemistry·Katarzyna BoberStanisław Boryczka
Oct 24, 2019·International Journal of Molecular Sciences·Elwira ChrobakStanisław Boryczka
Feb 13, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Elwira ChrobakStanisław Boryczka
Jan 29, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Arkadiusz OrchelJanusz Kasperczyk
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vuyolwethu KhwazaBlessing A Aderibigbe
Oct 1, 2021·Chemical Biology & Drug Design·Bhavna SarohaSuresh Kumar

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Methods Mentioned

BETA
column chromatography
NMR

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