New indane derivatives containing 2-hydrazinothiazole as potential acetylcholinesterase and monoamine oxidase-B inhibitors

Z Naturforsch C J Biosci. 2021 May 28;76(9-10):417-424. doi: 10.1515/znc-2021-0058. Print 2021 Sep 27.

Abstract

Although radical treatment of Alzheimer's and Parkinson's disease is not possible yet, it is aimed to slow the course of the disease and increase the life quality of individuals with the drugs used in the clinic at the present time. Successful results have been achieved in the use of cholinesterase inhibitors and monoamine oxidase inhibitors together in these neurodegenerative diseases. In this study, indane ring which are in the structure of anticholinesterase effective molecules and 2-hydrazinothiazole structure whose inhibitory activities reported on monoamine oxidase-B (MAO-B) were combined; 4-(substituted phenyl)-2-[2-(3-phenyl-2,3-dihydro-1H-inden-1-ylidene) hydrazinyl]thiazole derivatives (3a-3i) were synthesized as dual inhibitors. The structures of the compounds were verified by IR, 1H-NMR, 13C-NMR, and HRMS spectroscopy. When enzyme inhibition activities were evaluated, it was determined that the compounds 3a (42.33%) and 3d (42.39%) on acetylcholinesterase (AChE) enzyme; compounds 3g (75.42%) and 3h (60.33%) showed inhibition on MAO-B enzyme at most, at 10-3 M concentration.

Keywords: ADME prediction; anticholinesterase activity; indane; monoamine oxidase inhibition; thiazole.

MeSH terms

  • Cholinesterase Inhibitors / pharmacology*
  • Humans
  • Monoamine Oxidase / drug effects*
  • Monoamine Oxidase Inhibitors / chemistry
  • Monoamine Oxidase Inhibitors / pharmacology*
  • Spectrum Analysis / methods
  • Structure-Activity Relationship
  • Thiazoles / chemistry*

Substances

  • Cholinesterase Inhibitors
  • Monoamine Oxidase Inhibitors
  • Thiazoles
  • Monoamine Oxidase