Cerium(Ⅳ) ammonium nitrate(CAN)-mediated regioselective synthesis and anticancer activity of 6-substituted 5,8-dimethoxy-1,4-naphthoquinone

被引：0

作者：

Guang Huang ^{[1
,2
]}

Hui-Ran Zhao ^{[3
]}

Qing-Qing Meng ^{[1
]}

Wen Zhou ^{[1
]}

Qi-Jing Zhang ^{[1
]}

Jin-Yun Dong ^{[1
]}

Jia-Hua Cui ^{[1
]}

Shao-Shun Li ^{[1
]}

机构：

[1] School of Pharmacy,Shanghai Jiao Tong University

[2] Shanghai Institute of Pharmaceutical Industry

[3] School of Pharmaceutical Sciences and Chemistry,Dali University

来源：

ChineseChemicalLetters | 2017年 / 28卷 / 07期

基金：

中国国家自然科学基金;

关键词：

6-Substituted 5,8-O-dimethyl-1,4-; naphthoquinone; Cerium(Ⅳ) ammonium nitrate; Regioselective oxidation; Steric effects; Antitumor activity; Sulfur-containing;

D O I：

暂无

中图分类号：

TQ460.1 [基础理论];

学科分类号：

1007 ;

摘要：

6-Substituted 5,8-O-dimethyl-1,4-naphthoquinones(6-DMNQ),the promising anticancer scaffolds,were selectively generated by oxidative demethylation of 2-substituted 1,4,5,8-tetramethoxynaphthalenes with CAN in EtOAc/H2O in comparatively high yields.An interesting finding was that apart from the reported electron-withdrawing effects of substituents on position 2 of naphthalene ring,regioselective synthesis of 6-DMNQ was largely dependent on the steric effects in CAN-mediated oxidation.The selective cytotoxicities of 6-DMNQ from the in vitro cell-based assays were exhibited between the cancer cells and normal cells.Moreover,most of sulfur-containing 6-DMNQ derivatives displayed better anticancer activities than the corresponding oxygen-containing ones,which could provide an available strategy for the design of 6-DMNQ derivatives as potential anticancer agents.

引用

页码：1553 / 1558

页数：6

共 21 条

[1] Shikonin Derivative DMAKO-05 Inhibits Akt Signal Activation and Melanoma Proliferation [J].

Yang, Yao-yao ;

He, Hui-qiong ;

Cui, Jia-hua ;

Nie, Yun-juan ;

Wu, Ya-xian ;

Wang, Rui ;

Wang, Gang ;

Zheng, Jun-Nian ;

Ye, Richard D. ;

Wu, Qiong ;

Li, Shao-shun ;

Qian, Feng .

CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 87 (06) :895-904

[2]

Design, Synthesis, and Biological Evaluation of Shikonin and Alkannin Derivatives as Potential Anticancer Agents via a Prodrug Approach[J] . Ru‐Bing Wang,Wen Zhou,Qing‐Qing Meng,Xu Zhang,Jing Ding,Yan Xu,Hua‐Long Song,Kai Yang,Jia‐Hua Cui,Shao‐Shun Li.ChemMedChem . 2014 (12)

[3] Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents [J].

Wang, Rubing ;

Zhang, Xu ;

Song, Hualong ;

Zhou, Shanshan ;

Li, Shaoshun .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (17) :4304-4307

[4]

Synthesis of N ＜sup＞1＜/sup＞‐tritylethane‐1,1,2,2‐ d ＜sub＞4＜/sub＞‐1,2‐diamine: a novel mono‐protected C‐deuterated ethylenediamine synthon[J] . Jun Yang,Kunlun Hong,Peter V. Bonnesen.J. Label Compd. Radiopharm . 2012 (13)

[5]

Anti-proliferative actions of 2-decylamino-5,8-dimethoxy-1,4-naphthoquinone in vascular smooth muscle cells[J] . Jung-Jin Lee,Wei-Yun Zhang,Hyoseok Yi,Yohan Kim,In-Su Kim,Gui-Nan Shen,Gyu-Yong Song,Chang-Seon Myung.Biochemical and Biophysical Research Communications . 2011 (1)

[6]

Semi-synthesis and antitumor activity of 6-isomers of 5, 8- O -dimethyl acylshikonin derivatives[J] . Wen Zhou,Xu Zhang,Ling Xiao,Jing Ding,Quan-Hua Liu,Shao-Shun Li.European Journal of Medicinal Chemistry . 2011 (8)

[7]

Synthesis and antitumor activity of 6- and 2-（1-substituted-thio-4-methylpent-3-enyl）-5,8-dimethoxynaphthalene-1,4-diones[J] . Li-Ming Zhao,Tian-Pei Xie,Yu-Qin He,De-Feng Xu,Shao-Shun Li.European Journal of Medicinal Chemistry . 2008 (4)

[8]

6‐（1‐Oxobutyl）‐5,8‐dimethoxy‐1,4‐naphthoquinone inhibits lewis lung cancer by antiangiogenesis and apoptosis[J] . Hyo JeongLee,Hyo‐JungLee,Gyu‐YongSong,GuangxunLi,Jae‐HoLee,JunxuanLü,Sung‐HoonKim.Int. J. Cancer . 2007 (11)

[9]

Synthesis and evaluation of antitumor activity of 2- and 6-[（1,3-benzothiazol-2-yl）aminomethyl]-5,8-dimethoxy-1,4-naphthoquinone derivatives[J] . Yongseog Chung,Young-Kook Shin,Chang-Guo Zhan,Sungduck Lee,Hoon Cho.Archives of Pharmacal Research . 2004 (9)

[10]

Elucidation of structure–activity relationships for 2- or 6-substituted-5,8-dimethoxy-1,4-naphthoquinones[J] . Rajeshwar P. Verma,Corwin Hansch.Bioorganic ＆ Medicinal Chemistry . 2004 (22)

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