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Molecules 2015, 20(2), 3255-3280; doi:10.3390/molecules20023255

Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives

1
Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
2
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
3
Department of Chemistry, Lakehead University, 955 Oliver Road, Thunder Bay, ON P7B 5E1, Canada
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 11 January 2015 / Accepted: 4 February 2015 / Published: 16 February 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [911 KB, uploaded 16 February 2015]   |  

Abstract

A series of novel perbutyrylated glycosides of 4β-triazolopodophyllotoxin derivatives were synthesized by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Evaluation of cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using the MTT assay shows that some of these glycosylated derivatives have good anticancer activity. Among the synthesized compounds, compound 21a shows the highest activity, with IC50 values ranging from 0.49 to 6.70 μM, which is more potent than the control drugs etoposide and cisplatin. Compound 21a is characterized by a perbutyrylated α-D(+)-galactosyl residue, the absence of an additional linking spacer between the sugar residue and the triazole ring, as well as a 4'-OH group on the E ring of the podophyllotoxin scaffold. View Full-Text
Keywords: podophyllotoxin; glycosylated; 4β-triazole; CuAAC reaction; antitumor; synthesis podophyllotoxin; glycosylated; 4β-triazole; CuAAC reaction; antitumor; synthesis
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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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MDPI and ACS Style

Zi, C.-T.; Liu, Z.-H.; Li, G.-T.; Li, Y.; Zhou, J.; Ding, Z.-T.; Hu, J.-M.; Jiang, Z.-H. Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives. Molecules 2015, 20, 3255-3280.

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