Synthesis and decreasing Aβ content evaluation of arctigenin-4-yl carbamate derivatives

Bioorg Med Chem Lett. 2016 Jul 1;26(13):2988-2991. doi: 10.1016/j.bmcl.2016.05.028. Epub 2016 May 10.

Abstract

A series of arctigenin-4-yl carbamate derivatives were synthesized and evaluated for potency in reducing β-amyloid (Aβ) content in HEK293-APPswe cells. Most of the arctigenin-4-yl aralkyl or aryl carbamate derivatives showed improved potency in reducing Aβ content. Among the synthesized compounds, arctigenin-4-yl (3-chlorophenyl)carbamate (20) exhibited the strongest potency with 78.7% Aβ content reduction at 20μM. Furthermore, the effect of arctigenin-4-yl (4-chlorophenyl)carbamate (19) and arctigenin-4-yl (3-chlorophenyl)carbamate (20) on lowing Aβ content was better than arctigenin under the concentrations of 1, 10 and 20μM.

Keywords: Alzheimer’s disease (AD); Arctigenin (ATG); Arctigenin-4-yl 3-carbamate; Natural product; Structure–activity relationships (SARs).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amyloid beta-Peptides / metabolism*
  • Carbamates / chemical synthesis
  • Carbamates / chemistry
  • Carbamates / pharmacology*
  • Furans / chemical synthesis
  • Furans / chemistry
  • Furans / pharmacology*
  • HEK293 Cells
  • Humans
  • Lignans / chemical synthesis
  • Lignans / chemistry
  • Lignans / pharmacology*
  • Structure-Activity Relationship

Substances

  • Amyloid beta-Peptides
  • Carbamates
  • Furans
  • Lignans
  • arctigenin-4-yl (3-chlorophenyl)carbamate
  • arctigenin-4-yl (4-chlorophenyl)carbamate
  • arctigenin