Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities

Yanghan Liu; Qicai Xiao; Yongqiang Liu; Zheng Li; Yatao Qiu; Guang Biao Zhou; Zhu Jun Yao; Sheng Jiang

doi:10.1016/j.ejmech.2014.03.062

Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities

Yanghan Liu, Qicai Xiao, Yongqiang Liu, Zheng Li, Yatao Qiu, Guang Biao Zhou, Zhu Jun Yao, Sheng Jiang

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids.

Original language	English (US)
Pages (from-to)	248-258
Number of pages	11
Journal	European Journal of Medicinal Chemistry
Volume	78
DOIs	https://doi.org/10.1016/j.ejmech.2014.03.062
State	Published - May 6 2014

Keywords

Annonaceous acetogenins
Aromatic functionalities
Click chemistry
Cytotoxicity
Quinone

ASJC Scopus subject areas

Drug Discovery
Organic Chemistry
Pharmacology

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10.1016/j.ejmech.2014.03.062

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title = "Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities",

abstract = "A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids.",

keywords = "Annonaceous acetogenins, Aromatic functionalities, Click chemistry, Cytotoxicity, Quinone",

author = "Yanghan Liu and Qicai Xiao and Yongqiang Liu and Zheng Li and Yatao Qiu and Zhou, {Guang Biao} and Yao, {Zhu Jun} and Sheng Jiang",

note = "Funding Information: This work was supported by the National Key Program for Basic Research ( 2010CB529201 , 2012CB910800 , and 2009CB940900 ), the National Natural Science Foundation of China ( 21172220 , 81071930 , and 81171925 ), the Special Foundation of President , and the Strategic Leading Science & Technology Programme of the Chinese Academy of Sciences . ",

year = "2014",

month = may,

day = "6",

doi = "10.1016/j.ejmech.2014.03.062",

language = "English (US)",

volume = "78",

pages = "248--258",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson s.r.l.",

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TY - JOUR

T1 - Biological evaluation of new mimetics of annonaceous acetogenins

T2 - Alteration of right scaffold by click linkage with aromatic functionalities

AU - Liu, Yanghan

AU - Xiao, Qicai

AU - Liu, Yongqiang

AU - Li, Zheng

AU - Qiu, Yatao

AU - Zhou, Guang Biao

AU - Yao, Zhu Jun

AU - Jiang, Sheng

N1 - Funding Information: This work was supported by the National Key Program for Basic Research ( 2010CB529201 , 2012CB910800 , and 2009CB940900 ), the National Natural Science Foundation of China ( 21172220 , 81071930 , and 81171925 ), the Special Foundation of President , and the Strategic Leading Science & Technology Programme of the Chinese Academy of Sciences .

PY - 2014/5/6

Y1 - 2014/5/6

N2 - A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids.

AB - A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids.

KW - Annonaceous acetogenins

KW - Aromatic functionalities

KW - Click chemistry

KW - Cytotoxicity

KW - Quinone

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DO - 10.1016/j.ejmech.2014.03.062

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SN - 0223-5234

VL - 78

SP - 248

EP - 258

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities

Abstract

Keywords

ASJC Scopus subject areas

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