Synthesis and conformation studies of rubiyunnanin B analogs

doi:10.1016/j.tet.2014.06.108

	Synthesis and conformation studies of rubiyunnanin B analogs
	Liu, Na-Na 1; Zhao, Si-Meng 2,3; Zhao, Jing-Feng 1; Zeng, Guang-Zhi 2; Tan, Ning-Hua 2; Liu, Jian-Ping 1; 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
发表期刊	TETRAHEDRON
ISSN	0040-4020
卷号	70 期号:37 页码:6630-6640
摘要	Five 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.
关键词	Rubiyunnanin b Analogs Synthesis Conformation Studies Bioactivities
学科领域	Chemistry, Organic
DOI	10.1016/j.tet.2014.06.108
收录类别	SCI ; IC
语种	英语
WOS记录号	WOS:000340852900030
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/18256
专题	植物化学与西部植物资源持续利用国家重点实验室
通讯作者	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
作者单位	1.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
推荐引用方式 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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