N-Methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine, a new cholinesterase and monoamine oxidase dual inhibitor

J Med Chem. 2014 Dec 26;57(24):10455-63. doi: 10.1021/jm501501a. Epub 2014 Dec 8.

Abstract

On the basis of N-((5-(3-(1-benzylpiperidin-4-yl)propoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine (II, ASS234) and QSAR predictions, in this work we have designed, synthesized, and evaluated a number of new indole derivatives from which we have identified N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine (2, MBA236) as a new cholinesterase and monoamine oxidase dual inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Blood-Brain Barrier / drug effects
  • Brain / drug effects
  • Brain / enzymology
  • Cell Membrane Permeability / drug effects
  • Cholinesterase Inhibitors / chemical synthesis
  • Cholinesterase Inhibitors / pharmacology*
  • Cholinesterases / chemistry*
  • Indoles / chemical synthesis
  • Indoles / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Monoamine Oxidase / chemistry*
  • Monoamine Oxidase Inhibitors / chemical synthesis
  • Monoamine Oxidase Inhibitors / pharmacology*
  • Piperidines / chemical synthesis
  • Piperidines / pharmacology*
  • Swine

Substances

  • Cholinesterase Inhibitors
  • Indoles
  • Monoamine Oxidase Inhibitors
  • N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine
  • Piperidines
  • Monoamine Oxidase
  • Cholinesterases