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Molecules 2017, 22(11), 1876; doi:10.3390/molecules22111876

Novel Triazole Hybrids of Betulin: Synthesis and Biological Activity Profile

1
Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland
2
Department of Solid State Physics, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
3
Silesian Center for Education and Interdisciplinary Research, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland
4
Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Laboratory of Virology, 12 Rudolfa Weigla Str., 53-114 Wrocław, Poland
5
Department of Cell Biology, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 8 Jedności Str., 41-200 Sosnowiec
6
Department of Microbiology and Immunology, School of Medicine with the Division of Dentistry in Zabrze, Medical University of Silesia in Katowice, 19 Jordana Str., 41-808 Zabrze, Poland
*
Author to whom correspondence should be addressed.
Received: 16 October 2017 / Revised: 27 October 2017 / Accepted: 30 October 2017 / Published: 1 November 2017
(This article belongs to the Special Issue Emerging Drug Discovery Approaches against Infectious Diseases)
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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 5ak and 6ah 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. Klebsiella pneumoniae and Escherichia coli (minimal inhibitory concentration (MIC) range of 0.95–1.95 μM). View Full-Text
Keywords: betulin; 1,3-dipolar cycloaddition; triazoles; antiviral activity; anticancer activity; antimicrobial activity betulin; 1,3-dipolar cycloaddition; triazoles; antiviral activity; anticancer activity; antimicrobial activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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