Synthesis of cyclopentapyridine and thienopyridine derivatives as potential calcium channel modulators

Arzneimittelforschung. 2012 Apr;62(4):167-75. doi: 10.1055/s-0031-1299744. Epub 2012 Jan 27.

Abstract

In this study, novel condensed 1,4-dihydropyridines bearing cyclopentanone (1-21) or tetrahydrothiophene-1,1-dioxide ring (22-42) with various ester substituents were synthesized via a modified Hantzsch reaction and their calcium channel modulator activities were investigated on isolated rat ileum and rat thoracic aorta. The introduction of a cyclopentanone ring fused to the 1,4-dihydropyridine nucleus and methyl, ethyl and allyl moieties to the ester group led to more active calcium modulators.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aorta, Thoracic / drug effects
  • Calcium Channel Blockers / pharmacology
  • Calcium Channels / drug effects*
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / pharmacology*
  • Female
  • Ileum / drug effects
  • In Vitro Techniques
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Male
  • Models, Molecular
  • Muscle Relaxation / drug effects
  • Muscle, Smooth / drug effects
  • Nicardipine / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology*
  • Rats
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship
  • Tandem Mass Spectrometry
  • Thienopyridines / chemical synthesis*
  • Thienopyridines / pharmacology*

Substances

  • Calcium Channel Blockers
  • Calcium Channels
  • Cyclopentanes
  • Indicators and Reagents
  • Pyridines
  • Thienopyridines
  • Nicardipine