Synthesis of Dihydrobenzofuran Neoligans Licarin A and Dihydrocarinatin as Well as Related Triazolylglycosides

doi:10.1007/s40242-013-3131-6

高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (6): 1119-1124.doi: 10.1007/s40242-013-3131-6

Synthesis of Dihydrobenzofuran Neoligans Licarin A and Dihydrocarinatin as Well as Related Triazolylglycosides

LIU Shuang-yan, WANG Gang-qiang, LIANG Zhi-ying, WANG Qiu-an

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

收稿日期:2013-03-20 修回日期:2013-05-28 出版日期:2013-12-01 发布日期:2013-06-03
通讯作者: WANG Qiu-an E-mail:WangQA@hnu.edu.cn
基金资助:
Support by the Hunan Provincial Innovation Foundation for Postgraduate, China(No.CX2012B160) and the Personal Trai-ning Funds in National Basic Science of China(No. J1210040/J0104).

Synthesis of Dihydrobenzofuran Neoligans Licarin A and Dihydrocarinatin as Well as Related Triazolylglycosides

LIU Shuang-yan, WANG Gang-qiang, LIANG Zhi-ying, WANG Qiu-an

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

Received:2013-03-20 Revised:2013-05-28 Online:2013-12-01 Published:2013-06-03
Contact: WANG Qiu-an E-mail:WangQA@hnu.edu.cn
Supported by:
Support by the Hunan Provincial Innovation Foundation for Postgraduate, China(No.CX2012B160) and the Personal Trai-ning Funds in National Basic Science of China(No. J1210040/J0104).

摘要/Abstract

摘要：

Two natural dihydrobenzofuran neolignans licarin A(1) and dihydrocarinatin(2) were systhesized from isoeugenol with Ag₂O-catalyzed biomimetic oxidative coupling as the key step. Four novel dihydrobenzofuran triazolylglycoside(3―6) were achieved in good yields via Cu(I)-catalyzed azide-alkyne cycloadditions of licarin A terminal alkynes with different azide acetylated sugar and deacetylation with sodium methoxide in anhydrous methanol. The structures of all the compounds synthesized were determined by elemental analysis, MS, ¹H NMR and ¹³C NMR. And the inhibition activity of synthesized compounds on α-glucosidase was determined by in vitro experiments. The results show that triazolyglycosides 3, 4, 5 and 6 show moderate inhibitory activity on α-glucosidase.

关键词: Dihydrobenzofuran, Licarin A, Dihydrocarinatin, Triazolylglycoside

Abstract:

Key words: Dihydrobenzofuran, Licarin A, Dihydrocarinatin, Triazolylglycoside

LIU Shuang-yan, WANG Gang-qiang, LIANG Zhi-ying, WANG Qiu-an. Synthesis of Dihydrobenzofuran Neoligans Licarin A and Dihydrocarinatin as Well as Related Triazolylglycosides[J]. 高等学校化学研究, 2013, 29(6): 1119-1124.

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Synthesis of Dihydrobenzofuran Neoligans Licarin A and Dihydrocarinatin as Well as Related Triazolylglycosides

Synthesis of Dihydrobenzofuran Neoligans Licarin A and Dihydrocarinatin as Well as Related Triazolylglycosides

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