兰州大学机构库 >化学化工学院
Synthesis and structure-activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors
Yang, ZD; Song, ZW; Xue, WW; Sheng, J; Shu, ZM; Shi, Y; Liang, JB; Yao, XJ(姚小军); Yang, ZD (reprint author), Lanzhou Univ Technol, Sch Life Sci & Engn, Lanzhou 730050, Gansu, Peoples R China.
Indexed BySCIE
2014-06
Source PublicationMEDICINAL CHEMISTRY RESEARCH
Volume23Issue:6
PublisherSPRINGER
Publication PlaceNEW YORK
AbstractAcetylcholinesterase inhibitors (AChEIs) are currently the best available pharmacotherapy for Alzheimer patients, but because of bioavailability issues, there is still great interest in discovering better AChEIs. The aporphine alkaloid is an important class of natural products, which shows diverse biological activity, such as acetylcholinesterase inhibitory activity. To find new lead AChEIs compounds, eight aporphine alkaloids were synthesized by O-dealkylation, N-dealkylation, and ring aromatization reactions using nuciferine as raw material. The anti-acetylcholinesterase activity of synthesized compounds was measured using modified Ellman's method. The results showed that some synthesized compounds exhibited higher affinity to AChE than the parent compound nuciferine. Among these compounds, 1,2-dihydroxyaporphine (2) and dehydronuciferine (5) were the most active compounds (IC50 = 28 and 25 mu g/mL, respectively). Preliminary analysis of structure-activity relationships suggested that aromatization of the C ring, the presence of the alkoxyl group at C1 and the hydroxy group at C2 position as well as the alkyl substituent at the N atom were favorable to the acetylcholinesterase inhibition. Molecular docking was also applied to predict the binding modes of compounds 1, 2, and 9 into the huperzine A binding site of AChE.
KeywordAporphine alkaloids Acetylcholinesterase inhibitors Structure-activity relationships
Department[Yang, Zhongduo;
Song, Zhuwen;
Sheng, Jie;
Shu, Zongmei;
Liang, Jibei] Lanzhou Univ Technol, Sch Life Sci & Engn, Lanzhou 730050, Gansu, Peoples R China;
[Xue, Weiwei;
Yao, Xiaojun] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China;
[Shi, Yin] CAAS, Key Lab New Anim Drug Project, Key Lab Vet Pharmaceut Dev, Minist Agr,Lanzhou Inst Husb & Pharmaceut Sci, Lanzhou 730050, Gansu, Peoples R China
Subject AreaPharmacology & Pharmacy
Project NumberNational Natural Science Foundation of China [21262022] ; Elitist Program of Lanzhou University of Technology [J201303] ; Zhejiang Provincial Natural Science Foundation of China [LY12B02005]
Funding Project国家自然科学基金项目
Funding OrganizationNational Natural Science Foundation of China [21262022]; Elitist Program of Lanzhou University of Technology [J201303]; Zhejiang Provincial Natural Science Foundation of China [LY12B02005] ; NSFC
DOI10.1007/s00044-013-0905-9
ISSN1054-2523
SubtypeArticle
Language英语
WOS IDWOS:000334184400043
First Inst
Citation statistics
Cited Times:9[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.lzu.edu.cn/handle/262010/81949
Collection化学化工学院
Corresponding AuthorYang, ZD (reprint author), Lanzhou Univ Technol, Sch Life Sci & Engn, Lanzhou 730050, Gansu, Peoples R China.
Recommended Citation
GB/T 7714
Yang, ZD,Song, ZW,Xue, WW,et al. Synthesis and structure-activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors[J]. MEDICINAL CHEMISTRY RESEARCH,2014,23(6).
APA Yang, ZD.,Song, ZW.,Xue, WW.,Sheng, J.,Shu, ZM.,...&Yang, ZD .(2014).Synthesis and structure-activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors.MEDICINAL CHEMISTRY RESEARCH,23(6).
MLA Yang, ZD,et al."Synthesis and structure-activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors".MEDICINAL CHEMISTRY RESEARCH 23.6(2014).
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