Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4 beta-Triazolopodophyllotoxin Derivatives
Zi, Cheng-Ting1,2; Liu, Zhen-Hua2; Li, Gen-Tao2; Li, Yan2; Zhou, Jun2; Ding, Zhong-Tao1; Hu, Jiang-Miao2; Jiang, Zi-Hua3; Ding,ZT (reprint author),Yunnan Univ,Key Lab Med Chem Nat Resource,Minist Educ,Sch Chem Sci & Technol,Kunming 650091,Peoples R China.; zict@sina.cn; liuzhenhua@mail.kib.ac.cn; ligentao@mail.kib.ac.cn; liyanb@mail.kib.ac.cn; jzhou@mail.kib.ac.cn; ztding@ynu.edu.cn; hujiangmiao@mail.kib.ac.cn; zjiang@lakeheadu.ca
2015-02-01
Source PublicationMOLECULES
Volume20Issue:2Pages:3255-3280
AbstractA series of novel perbutyrylated glycosides of 4 beta-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 mu M, which is more potent than the control drugs etoposide and cisplatin. Compound 21a is characterized by a perbutyrylated alpha-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.
Subject AreaChemistry, Organic
DOI10.3390/molecules20023255
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000350748200086
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/20629
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorDing,ZT (reprint author),Yunnan Univ,Key Lab Med Chem Nat Resource,Minist Educ,Sch Chem Sci & Technol,Kunming 650091,Peoples R China.; zict@sina.cn; liuzhenhua@mail.kib.ac.cn; ligentao@mail.kib.ac.cn; liyanb@mail.kib.ac.cn; jzhou@mail.kib.ac.cn; ztding@ynu.edu.cn; hujiangmiao@mail.kib.ac.cn; zjiang@lakeheadu.ca
Affiliation1.Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Sch Chem Sci & Technol, Kunming 650091, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
3.Lakehead Univ, Dept Chem, Thunder Bay, ON P7B 5E1, Canada
Recommended Citation
GB/T 7714
Zi, Cheng-Ting,Liu, Zhen-Hua,Li, Gen-Tao,et al. Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4 beta-Triazolopodophyllotoxin Derivatives[J]. MOLECULES,2015,20(2):3255-3280.
APA Zi, Cheng-Ting.,Liu, Zhen-Hua.,Li, Gen-Tao.,Li, Yan.,Zhou, Jun.,...&zjiang@lakeheadu.ca.(2015).Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4 beta-Triazolopodophyllotoxin Derivatives.MOLECULES,20(2),3255-3280.
MLA Zi, Cheng-Ting,et al."Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4 beta-Triazolopodophyllotoxin Derivatives".MOLECULES 20.2(2015):3255-3280.
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