Triazole-linked Benzylated Glucosyl, Galactosyl, and Mannosyl Monomers and Dimers as Novel Sugar Scaffold-based PTP1B Inhibitors

被引：16

作者：

Zhang, Yin Jie ^{[1
,2
]}

He, Xiao-Peng ^{[4
,5
]}

Li, Cui ^{[4
]}

Li, Zhen ^{[1
,2
]}

Shi, De-Tai ^{[1
,2
]}

Gao, Li-Xin

Qiu, Bei-Ying ^{[3
]}

Shi, Xiao-Xin ^{[4
]}

Tang, Yun ^{[4
]}

Li, Jia ^{[3
]}

Chen, Guo-Rong ^{[1
,2
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Natl Ctr Drug Screening, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

[4] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

[5] CNRS, PPSM, ENS Cachan, F-94230 Cachan, France

来源：

CHEMISTRY LETTERS | 2010年 / 39卷 / 12期

基金：

中国国家自然科学基金;

关键词：

TYROSINE-PHOSPHATASE; 1B; CLICK-CHEMISTRY; DISCOVERY;

D O I：

10.1246/cl.2010.1261

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Monomeric and dimeric benzylated glycosyl benzenes were synthesized via copper-catalyzed [3 + 2] azide-alkyne cycloaddition These compounds were then identified as protein tyrosine phosphatase (PTP) 1B inhibitors which displayed at least several fold selectivity over other homologous PTPases The glucosyl, galactosyl, and mannosyl inhibitors exhibited different biological profiles, suggesting the monosaccharides may qualify as chiral scaffolds for probing the spatial preference of PTP1B Furthermore, docking study suggested a plausible binding mode of this glycoside series with the enzymatic target

引用

页码：1261 / 1263

页数：3

共 17 条

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Lin, Li
Shen, Qiang
Chen, Guo-Rong
Xie, Juan
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (22) : 9757 - 9763
[2] Preparation of triazole-linked glycosylated α-ketocarboxylic acid derivatives as new PTP1B inhibitors
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He, Xiao-Peng
Li, Cui
Gao, Li-Xin
Wang, Zhao-Xia
Tang, Yun
Xie, Juan
Li, Jia
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CARBOHYDRATE RESEARCH, 2011, 346 (01) : 140 - 145
[3] Microwave-assisted construction of triazole-linked amino acid-glucoside conjugates as novel PTP1B inhibitors
He, Xiao-Peng
Li, Cui
Jin, Xiao-Ping
Song, Zhuo
Zhang, Hai-Lin
Zhu, Cheng-Jiang
Shen, Qiang
Zhang, Wei
Sheng, Li
Shi, Xiao-Xin
Tang, Yun
Li, Jia
Chen, Guo-Rong
Xie, Juan
NEW JOURNAL OF CHEMISTRY, 2011, 35 (03) : 622 - 631
[4] Synthesis of Triazole-Linked Amino Acid-Aryl C-Glycoside Hybrids via Click Chemistry as Novel PTP1B Inhibitors
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Gao Lixin
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Shi Xiaoxin
Li Jia
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CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (06) : 1227 - 1232
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Dixit, Manish
Tripathi, Brajendra K.
Tamrakar, Akhilesh K.
Srivastava, Arvind K.
Kumar, Brijesh
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BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (02) : 727 - 734
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Balaramnavar, Vishal M.
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Rahuja, Neha
Gupta, Swati
Rawat, Arun K.
Varshney, Salil
Chandasana, Hardik
Chhonker, Yashpal S.
Doharey, Pawan Kumar
Kumar, Santosh
Gautam, Sudeep
Srivastava, Swayam Prakash
Bhatta, Rabi Sankar
Saxena, Jitendra Kumar
Gaikwad, Anil Nilkanth
Srivastava, Arvind K.
Saxena, Anil K.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 87 : 578 - 594
[7] Microwave-Accelerated Click Chemistry: Expeditious Synthesis of Novel Triazole-linked Salicylic β-D-O-Glycosides with PTP1B Inhibitory Activity
Yang, Jin-Wei
Li, Cui
He, Xiao-Peng
Zhao, Hong
Gao, Li-Xin
Zhang, Wei
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Tang, Yun
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Chen, Guo-Rong
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (11) : 3359 - 3365
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Chai Qian
Shen Qiang
Ma Lan-Ping
Wang Xin
Meng Tao
Li Jing-Ya
Li Jia
Shen Jing-Kang
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2011, 32 (02): : 306 - 315
[9] Click to a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides: Novel construction of PTP1B inhibitors on a sugar scaffold
Li, Cui
He, Xiao-Peng
Zhang, Yin-Jie
Li, Zhen
Gao, Li-Xin
Shi, Xiao-Xin
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Li, Jia
Chen, Guo-Rong
Tang, Yun
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) : 4212 - 4218
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Nie, Feilin
Yang, Ying
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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (23) : 6217 - 6222

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