Synthesis and conformation studies of rubiyunnanin B analogs
Liu, Na-Na1; Zhao, Si-Meng2,3; Zhao, Jing-Feng1; Zeng, Guang-Zhi2; Tan, Ning-Hua2; Liu, Jian-Ping1; Tan, NH (reprint author), Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China.; nhtan@mail.kib.ac.cn; jpliu@ynu.edu.cn
2014-09-16
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume70Issue:37Pages:6630-6640
Contribution Rank第二
AbstractFive new analogs 4-8 of rubiyunnanin B (1), mainly modified on the tetrapeptide subunit, were synthesized. These agents 4-8 were substituted D-Ala-L-Ala-L-Tyr(OMe)-L-Ala, D-Ala-L-Ala-L-Phe-L-Ala, D-Ala-L-Ala-L-Tyr-L-Ala, D-Ala-L-Ala-L-Pro-L-Ala, and D-Ala-L-Ala-L-Ala for the D-Ala-L-Ala-c-N-Me-Tyr(OMe)-L-Ala tetrapeptide subunit. Unlike the natural product, the synthetic agents 4-8 adopt only a single solution conformation, and the central peptide bond in the cyclodityrosine subunit of compounds 4-8 adopt trans stereochemistry. Cytotoxic activities of analogs 4-8 against three human cancer cell lines including A549, BGC-823, and HeLa were evaluated and all the five synthesized peptides exhibited no effects against the test cell lines. These compounds were also evaluated for their antiinsulin resistance and insulin sensitizing activities and none of them showed activity in these assays. (C) 2014 Elsevier Ltd. All rights reserved.
KeywordRubiyunnanin b Analogs Synthesis Conformation Studies Bioactivities
Subject AreaChemistry, Organic
DOI10.1016/j.tet.2014.06.108
Indexed BySCI ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000340852900030
Citation statistics
Cited Times:11[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/18256
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorTan, NH (reprint author), Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China.; nhtan@mail.kib.ac.cn; jpliu@ynu.edu.cn
Affiliation1.Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, 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.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Liu, Na-Na,Zhao, Si-Meng,Zhao, Jing-Feng,et al. Synthesis and conformation studies of rubiyunnanin B analogs[J]. TETRAHEDRON,2014,70(37):6630-6640.
APA Liu, Na-Na.,Zhao, Si-Meng.,Zhao, Jing-Feng.,Zeng, Guang-Zhi.,Tan, Ning-Hua.,...&jpliu@ynu.edu.cn.(2014).Synthesis and conformation studies of rubiyunnanin B analogs.TETRAHEDRON,70(37),6630-6640.
MLA Liu, Na-Na,et al."Synthesis and conformation studies of rubiyunnanin B analogs".TETRAHEDRON 70.37(2014):6630-6640.
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