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Chemical Research in Chinese Universities

, Volume 34, Issue 4, pp 571–577 | Cite as

Synthesis of 9-Substituted Berberine Derivatives with Microwave Irradiation

  • Xie Han
  • Kaiyuan Shao
  • Wenxiang Hu
Article
  • 35 Downloads

Abstract

Hyperglycemia is frequently accompanying with hyperlipidemia. To explore the potent drugs with dual-activity and dual-site effects that could reduce blood glucose and blood lipid at the same time, fibrate group with lipid-lowering effect on the 9th position of berberine(BBR) was introduced using the drug design combination principle and the multitarget collaborative treatment method. Moreover, the molecular structure of BBR was modified, and six 9-substituted derivatives of BBR were designed and synthesized, among which, five compounds have never been reported before. In addition, the molecular structures of these derivatives were identified using liquid chromatography-mass spectrometry(LC-MS), 1H nuclear magnetic resonance(1H NMR) and 13C NMR, respectively. Furthermore, the microwave irradiation experimental technique was applied in the synthesis reaction using the novel microwave synthesizer, which accelerated the reaction rate, enhanced the reaction yield, reduced the reaction by-products, and simplified the post-processing steps. In the meantime, the 9-position regioselective demethylation of BBR was explored through quantum chemical calculation during the synthesis of berberrubine. The computations were consistent with the experimental results, which contributed to deducing the mechanism of its selective methylation.

Keywords

Berberine derivative Microwave irradiation Quantum chemistry Regioselectivity 

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Supplementary material

40242_2018_7425_MOESM1_ESM.pdf (2.6 mb)
Synthesis of 9-Substituted Berberine Derivatives with Microwave Irradiation

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Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Chemical Engineering and PharmacyWuhan Institute of TechnologyWuhanP. R. China
  2. 2.Jingdong Xianghu Microwave Chemistry Union LaboratoryBeijing Excalibur Space Military Academy of Medical SciencesBeijingP. R. China
  3. 3.Space Systems Division, Strategic Support TroopsChinese People’s Liberation ArmyBeijingP. R. China

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