The total synthesis of berberine and selected analogues, and their evaluation as amyloid beta aggregation inhibitors

The total synthesis of berberine and selected analogues. And their evaluation as amyloid β (Aβ) aggregation inhibitors is described. The key step in the synthesis, the assembly of the berberine framework, was accomplished using an intermolecular Heck reaction. Berberine analog 17 incorporating a ter...

Full description

Saved in:
Bibliographic Details
Published in:European journal of medicinal chemistry 2021-04, Vol.215, p.113289-113289, Article 113289
Main Authors: Tajiri, Misato, Yamada, Ryo, Hotsumi, Mayumi, Makabe, Koki, Konno, Hiroyuki
Format: Article
Language:English
Subjects:
Aggregation inhibition
Alzheimer’s disease
Amyloid beta
Berberine
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The total synthesis of berberine and selected analogues. And their evaluation as amyloid β (Aβ) aggregation inhibitors is described. The key step in the synthesis, the assembly of the berberine framework, was accomplished using an intermolecular Heck reaction. Berberine analog 17 incorporating a tertiary amine moiety showed good anti Aβ aggregation activity, water solubility, and almost no toxicity to nerve cells. [Display omitted] •The total synthesis of berberine (1) has been accomplished and its analogues were prepared for the evaluation as Aβ aggregation inhibitors.•Berberine (1) was found to inhibit moderate Aβ aggregation inhibitory activity and the synthetic intermediates showed no activity, demonstrating the necessity of the berberine framework.•Tertiary amine (17) has excellent Aβ aggregation inhibitory activity, as well as good water solubility and low cytotoxicity.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2021.113289