Synthesis, structural characterization and myorelaxant activity of 4-naphthylhexahydroquinoline derivatives containing different ester groups

Abstract

The present study reports the synthesis, structural characterization and myorelaxant activity evaluation of a series of 16 novel 4-naphthyl-hexahydroquinoline derivatives. The compounds were achieved by one-pot microwave-assisted method via a modified Hantzsch reaction. The structures of the compounds were confirmed by various spectral methods like IR, 1D-2D NMR techniques and mass analysis. X-ray studies of compound 10 provided further evidence for the proposed structure. To evaluate their myorelaxant activities, the Emax and pD2 values of the compounds and nifedipine were determined on isolated rabbit gastric fundus smooth muscle strips. The obtained results indicated that introduction of long chain alkyl groups such as 2-methoxyethyl or 2-(methacryloyloxy)ethyl moiety to the ester group led to the most active compounds.

Keywords

• 1,4-dihydropyridine
• synthesis
• myorelaxant activity
• crystal structure
• structure elucidation