Synthesis and mechanistic evaluation of novel N'-benzylidene-carbohydrazide-1H-pyrazolo[3,4-b]pyridine derivatives as non-anionic antiplatelet agents

Eur J Med Chem. 2017 Jul 28:135:213-229. doi: 10.1016/j.ejmech.2017.04.023. Epub 2017 Apr 14.

Abstract

Cardiovascular diseases (CVDs) account for over 17 million deaths globally each year, with atherosclerosis as the underlying cause of most CVDs. Herein we describe the synthesis and in vitro mechanistic evaluation of novel N'-benzylidene-carbohydrazide-1H-pyrazolo[3,4-b]pyridines (3-22) designed as non-anionic antiplatelet agents and presenting a 30-fold increase in potency compared to aspirin. The mechanism underlying their antiplatelet activity was elucidated by eliminating potential targets through a series of in vitro assays including light transmission aggregometry, clot retraction, and quantitative ELISA, further identifying the reduction in biosynthesis of thromboxane B2 as their main mechanism of action. The intrinsic fluorescence of the compounds permits their binding to platelet membranes to be readily monitored. In silico structure-activity relationship, molecular docking and dynamics studies support the biological profile of the series revealing the molecular basis of their activity and their potential as future molecular therapeutic agents.

Keywords: Antiplatelet agents; Cardiovascular diseases; Drug design; Pyrazolopyridines; Thrombosis.

MeSH terms

  • Benzylidene Compounds / chemistry
  • Benzylidene Compounds / pharmacology*
  • Blood Platelets / drug effects*
  • Dose-Response Relationship, Drug
  • Humans
  • Hydrazines / chemistry
  • Hydrazines / pharmacology*
  • Molecular Docking Simulation
  • Molecular Structure
  • Platelet Aggregation Inhibitors / chemical synthesis
  • Platelet Aggregation Inhibitors / chemistry
  • Platelet Aggregation Inhibitors / pharmacology*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Structure-Activity Relationship

Substances

  • 1H-pyrazolo(3,4-b)pyridine
  • Benzylidene Compounds
  • Hydrazines
  • Platelet Aggregation Inhibitors
  • Pyrazoles
  • Pyridines
  • carbohydrazide