Synthesis of novel N-benzyl substituted piperidine amides of 1H-indole-5-carboxylic acid as potential inhibitors of cholinesterases

Acta Pol Pharm. 2012 May-Jun;69(3):449-55.

Abstract

A series of novel N-benzyl substituted amides of 1H-indole-5-carboxylic acid were synthesized and evaluated for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The target compounds (6b-6e) displayed moderate potency to inhibit BuChE. One of the compounds tested, i.e., 1-benzylpiperidine amide of 1H-indole-5-carboxylic acid (6a) was a weak, non-selective inhibitor for both enzymes. The highest inhibitory activity towards BuChE (30.06% [10 microM]) was determined for compound (6c) which is 1-(3-chloro)benzylpiperidine amide of 1H-indole-5-carboxylic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butyrylcholinesterase / chemical synthesis
  • Butyrylcholinesterase / chemistry
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry*
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cholinesterase Inhibitors / chemistry*
  • Cholinesterases / metabolism*
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry*

Substances

  • Carboxylic Acids
  • Cholinesterase Inhibitors
  • Indoles
  • Piperidines
  • 1-benzylpiperidine
  • indole
  • Butyrylcholinesterase
  • Cholinesterases