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Synthesis, Crystal Structure, and Biological Evaluation of Fused Thiazolo[3,2-a]Pyrimidines as New Acetylcholinesterase Inhibitors.

ABSTRACT: A new series of thiazolo[3,2-a]pyrimidine bromide salt derivatives 7a-d were synthesized from 3,4-dihydropyrimidinethione precursors. The target compounds were fully characterized by 1D- and 2D-NMR, high resolution ESI-MS/MS and single crystal X-ray diffraction analysis, which confirmed a regioselective 5H cyclization of the dihydropyrimidinethiones. All target compounds were evaluated in vitro as human acetylcholinesterase (hAChE) inhibitors via an Ellman-based colorimetric assay and showed good inhibition activities (better than 70% at 10 µM and IC50 values in the 1 µM range). Molecular docking simulations for all target products into hAChE were performed and confirmed strong binding to the enzyme. These results provide a promising and new starting point to improve acetylcholinesterase inhibitors and explore novel treatment options against Alzheimer's disease.

SUBMITTER: Mahgoub MY 

PROVIDER: S-EPMC6630738 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Synthesis, Crystal Structure, and Biological Evaluation of Fused Thiazolo[3,2-<i>a</i>]Pyrimidines as New Acetylcholinesterase Inhibitors.

Mahgoub Mohamed Y MY   Elmaghraby Awatef M AM   Harb Abd-Elfttah A AA   Ferreira da Silva João L JL   Justino Gonçalo C GC   Marques M Matilde MM  

Molecules (Basel, Switzerland) 20190621 12

A new series of thiazolo[3,2-<i>a</i>]pyrimidine bromide salt derivatives <b>7a</b>-<b>d</b> were synthesized from 3,4-dihydropyrimidinethione precursors. The target compounds were fully characterized by 1D- and 2D-NMR, high resolution ESI-MS/MS and single crystal X-ray diffraction analysis, which confirmed a regioselective 5<i>H</i> cyclization of the dihydropyrimidinethiones. All target compounds were evaluated in vitro as human acetylcholinesterase (<i>h</i>AChE) inhibitors via an Ellman-base  ...[more]

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