Reductive Amination of Genipin with NaBH<sub>3</sub>CN to Synthesize Alkaloid-likes and Bioactivity

Jie-chen QIN; Xiao-juan ZENG; Shao-xiang ZHANG; Xiao-mei ZHANG; Xin-yang LIU; Cheng ZOU; Qing ZHAO

doi:10.12259/j.issn.2095-610X.S20210216

Volume 42 Issue 2

Mar. 2021

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Article Navigation > Journal of Kunming Medical University > 2021 > 42(2): 18-22

Jie-chen QIN, Xiao-juan ZENG, Shao-xiang ZHANG, Xiao-mei ZHANG, Xin-yang LIU, Cheng ZOU, Qing ZHAO. Reductive Amination of Genipin with NaBH3CN to Synthesize Alkaloid-likes and Bioactivity[J]. Journal of Kunming Medical University, 2021, 42(2): 18-22. doi: 10.12259/j.issn.2095-610X.S20210216

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Jie-chen QIN, Xiao-juan ZENG, Shao-xiang ZHANG, Xiao-mei ZHANG, Xin-yang LIU, Cheng ZOU, Qing ZHAO. Reductive Amination of Genipin with NaBH₃CN to Synthesize Alkaloid-likes and Bioactivity[J]. Journal of Kunming Medical University, 2021, 42(2): 18-22. doi: 10.12259/j.issn.2095-610X.S20210216

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Reductive Amination of Genipin with NaBH₃CN to Synthesize Alkaloid-likes and Bioactivity

doi: 10.12259/j.issn.2095-610X.S20210216

1.
School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products，Kunming Medical University，Kunming Yunnan 650500
2.
Faculty of Pharmacy，Yunnan University of Chinese Medicine，Kunming Yunnan 650500，China

Received Date: 2020-11-04
Publish Date: 2021-02-25

Abstract

Abstract

Objective To explore a method for the synthesis of alkaloid-likes from Genipin by reductive amination is reported. Methods The reduction of Genipin and amines in the presence of sodium cyanoborohydride: after the methanol solution of Genipin and arylethylamine was mixed, excessive sodium cyanoborohydride was added and the reaction was kept at room temperature for 3 days. The product was eluted and separated on silica gel by petroleum ether-isopropyl alcohol-diethylamine and petroleum ether-ethyl acetate. Results Nine alkaloid-likes were synthesized. Some alkaloid-likes were screened for inhibition activity of PTP1B enzyme for Ⅱ diabetes treatment. Conclusions All of the tested compounds have a certain inhibitory effect on PTP1B. The acquisition of a series of active derivatives has laid a foundation for the study of the structure-activity relationship between the compounds and their bioactivities, so as to facilitate the search for more active PTP1B inhibitors.
- Genipin,
- Alkaloid-likes,
- Reductive amination,
- Inhibition activity against PTP1B

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References(17)

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