Synthesis of deoxy-Andrographolide Triazolyl Glycoconjugates for the Treatment of Alzheimer’s Disease

Abstract

A new andrographolide-based terminal alkyne 3 was synthesized in good yield from deoxy-andrographolide 2, obtained from a natural compound andrographolide 1, which in turn was isolated from the leaves of the plant Andrographis paniculata.Copper(I)-catalyzed azide−alkyne cycloaddition reaction of alkyne 3 with azido-sugars 4a−f furnished a library of andrographolidefastened triazolyl glycoconjugates 5a−f in good yields. The structures of these semisynthetic andrographolide derivatives were established by Fourier transform infrared, NMR, and mass spectroscopy. The compounds 5a−f were further evaluated against Alzheimer's disease (AD) using a scopolamine (SCOP)-induced memory impairment mice model. It was observed that antioxidant and anticholinesterase properties of these compounds contribute significantly toward their remarkable potential to improve cognitive functioning.