Synthesis and Antidiabetic Activity of Tropinone Derivatives

doi:10.3724/SP.J.1095.2013.20593

Chinese Journal of Applied Chemistry

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Synthesis and Antidiabetic Activity of Tropinone Derivatives

XIE Zhaoyang¹, LI Zhiwei², BAO Zhichao¹, WANG Jiannan¹, YIN Peng³, HE Kan¹, YAN Fei¹, ZHENG Qunyi^1,4*

(1.Herbalife Natsource(Hunan) Natual Products Corporation,Changsha 410100,China;
2.School of Chemistry and Biological Engineering,Changsha University of Science & Technology,Changsha 410114,China；
3.Natsource Chemical(Changsha) Corporation,Changsha 410329,China;
4.College of Chemistry and Chemical Engineering,Hunan University,Changsha 410082,China)

Received:2012-12-18 Revised:2013-02-14 Published:2013-10-10 Online:2013-10-10

Abstract

Abstract: 6-Hydroxytropinone was chosen as the primary precursor and subjected to a series of reactions including acetylation or benzoylation of its hydroxyl group, reduction and ammoniation of its keto group to yield two compounds containing tropane with primary amine core structure. A series of N-acyl compounds has been prepared by the reactions of the core structures with a variety of acyl chlorides. These compounds were screened in peroxisome proliferateive activeated recaptor-γ(PPARγ) and dipeptidylpeptidase-Ⅳ(DPP-Ⅳ） in-vitro models. Most of these compounds displayed inhibitory effect against DPP-Ⅳ and two of them showed inhibitory rates higher than 30% at 3 μmol/L in DMSO. But no activation toward PPARγ of all compounds could be observed.

Key words: tropinone derivaties, diabetes, In-vitro model, dipeptidylpeptidase-IV inhibitory effect

CLC Number:

O629.3

XIE Zhaoyang1, LI Zhiwei2, BAO Zhichao1, WANG Jiannan1, YIN Peng3, HE Kan1, YAN Fei1, ZHENG Qunyi1,4*. Synthesis and Antidiabetic Activity of Tropinone Derivatives[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20593.

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Synthesis and Antidiabetic Activity of Tropinone Derivatives

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